How to wear dresses without being dressy?
March 22, 2013 12:35 PM   Subscribe

Are you a woman who wears skirts and dresses casually? Can you teach me your secrets?

I live in jeans. Seriously. I have a few pairs of dress pants for special occasions. And I wear dresses to weddings. My office is casual, so I get away with wearing solid or patterned shirts with scarves, sweaters, or blouses... with jeans. But I like skirts, and I'd like to wear more skirts or even dresses. I'd like it even more if I could wear them when I'm just running errands, or during a gaming night, or grabbing lunch with friends. It seems like every time I try though, I either end up super-overdressed, or just... really awkward. I have a lot of questions about skirts.
  • What do you wear under them? I understand that pantyhose is way too formal, but tights and leggings are both in? Can you do bare-legs if your skin tone is somewhere between ivory and glow-in-the-dark?
  • What is the deal with shoes? I have two great pairs of boots and some sneakers. I also have an awesome pair of black patent pumps, but I think those are too fancy for casual wear. How do you know what shoes to wear with a skirt?
  • What kind of skirts are flattering, comfortable, and casual? Is there anything out there that matches the convenience and comfort of jeans? BONUS: are there any skirts that look okay with nerdy printed t-shirts, without being too pre-teen?
Extra info: I'm a 26-year old woman with a fairly average body, slightly bigger in the hips. This is a pretty accurate depiction of my daily office wear, although I don't have all the fancy shoes or purses. For my bumming around, sub out the nice shirts for shirt-a-day printed shirts with gaming or Doctor Who references.
posted by specialagentwebb to Clothing, Beauty, & Fashion (71 answers total) 106 users marked this as a favorite
Boots. Tall boots.
posted by feral_goldfish at 12:37 PM on March 22, 2013 [5 favorites]

I wear a lot of Old Navy skirts and dresses. They are casual as heck and cute. In the winter I wear pantyhose and then go bare legged once it hits 70 or so.

For shoes, I wear sandals or boots or flats.
posted by roomthreeseventeen at 12:38 PM on March 22, 2013

Or ballet flats. Tights only if dictated by weather. Try denim or canvas for casual wear.
posted by Pomo at 12:38 PM on March 22, 2013 [1 favorite]

Best answer: I either end up super-overdressed, or just... really awkward.

Oh gosh, I made the transition from "jeans always" to "casual skirts and dresses sometimes" a few years ago, and honestly the trick is to just jump in! You will get the hang of it! Sometimes I still feel super-awkward but that is usually just me! No one else is judging what I wear in any meaningful way.

What do you wear under them?

I am prone to thigh chafing, so in the summer I wear cotton shorts. In the winter I wear opaque tights or leggings

Can you do bare-legs if your skin tone is somewhere between ivory and glow-in-the-dark?

Yes! Own the skin you're in! I am very pale, have several big scars, and don't shave my legs, and I still go bare-legged. It's a mental trick - literally no one you care about is scrutinizing your legs for flaws.

What is the deal with shoes? I have two great pairs of boots and some sneakers. I also have an awesome pair of black patent pumps, but I think those are too fancy for casual wear. How do you know what shoes to wear with a skirt?

I usually wear a pair of flats, or a pair with a slight wedge heel, or flip flops, or sandals, or cowboy boots, or ankle boots. It depends on the season.
posted by muddgirl at 12:43 PM on March 22, 2013 [17 favorites]

Best answer: What do you wear under them?
Nothing, if possible. Tights/leggings are okay-ish while it's still cold outside, but they're a fading fashion. Personally, I'm just waiting until it's warm enough that I can go bare-legged. Or you can wear bloomers! They're super helpful when the hot, sticky weather rolls around.

What is the deal with shoes?
For office-wear, flats. Otherwise, sandals. The great thing is you can get away with the craziest flats if you're wearing a skirt. Some flats I would wear with skirts.

What kind of skirts are flattering, comfortable, and casual?
This depends to a degree on your body shape, but generally I'd go with above-the-knee skirts. Personally I prefer fuller skirts with a fitted top, and pencil skirts.
posted by DoubleLune at 12:47 PM on March 22, 2013 [4 favorites]

Best answer: Some skirts, paired with outfits. I am 34, live in a temperate zone, and wear a lot of jeans as well. However, I rarely wear a shirt with anything written on it. It should also be noted that although average weight I am a FF cup, so I tend toward the knit and stretchy on top.

I have a very outdoorsy skirt I like to wear in the summer; it's khaki and a-line and I wear it with sandals of all kinds and a t-shirt. Sandals could be silver Birkenstocks or wedgy t-straps from Clarks. I have been known to wear this skirt with knee-high boots in cooler weather.

I also have a red cord miniskirt I wear in the winter with fleece-lined leggings and one of several kinds of boots, always flat -- wearing it with heels is more Car-camping Hooker than I'm comfortable with at the office (although that's probably a pretty good description of my weekend attire overall...)

The holy grail for me is a denim pencil skirt cut for a curvy butt that does not contain actual shapewear. If I owned such a thing my life would be complete. I would wear it with flat boots, a band t-shirt and a hoodie, or flat boots and a scoop-neck top and a scarf, or flat boots etc. You get the idea.
posted by chesty_a_arthur at 12:49 PM on March 22, 2013 [1 favorite]

Black pumps with jeans can look good and casual. Black pumps with a skirt or dress will always be way too formal for casual wear.

Basic sneakers (like converse) or similar casual shoes with a simple casual dress can work pretty well. This can look even better with brightly colored ankle socks in a contrasting color.

Maybe consider a denim skirt?
posted by steinwald at 12:50 PM on March 22, 2013 [1 favorite]

I wear skirts with T-shirts, and both dresses and skirts with sneakers.
For the T-shirt skirts, I like plain ones, black or gray or white, knee-length or so.
posted by mlle valentine at 12:51 PM on March 22, 2013

I wear skirts all the time. In the winter it's tights or leggings, in the summer nothing. I'm pretty pale, but I haven't blinded anyone yet, so I don't worry about it.

As for shoes, in the summer I wear a pair of sandals or clogs, and in the winter I wear a pair of boots or clogs. My cowboy boots are year-round wear, depending on the skirt.
posted by carolinecrane at 12:52 PM on March 22, 2013

I'm a dress girl. I think the last time I wore pants was in 2010. Seriously. I wear them to work, I wear them at home, I wear them everywhere.

The secret to dresses is first embracing the fact that a dress, in and of itself, is not necessarily dressy. I grew up thinking that the only way to dress casually was to wear jeans. I hate jeans. They never fit me (I have a very small waist with larger hips) and I spent SOOOO many years trying to find ones that would. Since switching to dresses I am a woman liberated (some irony there!)

Once I got over the mental hurdle that dresses could be casual, I came to realize just how many casual dresses there are out there. After all, there is a big difference between this and this.

Fabric has a lot to do with it. Cotton or linen mixes read casual to me.

As a Canadian, I wear black tights (with feet) all winter long - with boots on my way to work, switching into shoes with a bit of heel for the office. In the summer, I go barelegged with sandals or flats. Kitten heels can also read more casual.

Online shopping is also a great resource for casual-y dresses. In my experience, dress sizing is easier to judge from basic measurements than it is for other articles of clothing. Some of my favorite sites are:

Dress 911
posted by elkerette at 12:52 PM on March 22, 2013 [5 favorites]

Best answer: As far as covering your legs - do it if you feel like it, if it's cold, if you have nifty stockings or leggings, but if you don't, by god, don't. Believe me, pale white legs are not unusual! If they bother you, you can grab some rub on home tanner but honestly, I don't bother; I wear dresses daily, all year round.

In the summer I wear flip flops and sandals, if my dress is particularly sporty I'll wear slip on canvas tennies, but I've got a couple of pairs of black leather mules that basically go with everything. In the winter, of course, boots, but depending on the weather, pretty much anything with closed toes.

I think longish, not-quite-maxi type skirts would look good with t shirts, with it getting to be spring that kind of slouchy boho look would be a nice change from winter. And yeah, denim and khaki are great for casual skirts, but at the same time, so are those gauzy broomstick ones.
posted by lemniskate at 12:52 PM on March 22, 2013

I wear skirts to the office everyday. Full suits with hose if there are meetings, but most days just knee-length skirts or dresses. If it's winter, I wear tights and in summer, bare legs. Boots or closed toe shoes in winter, dressy sandals or pumps in summer. I don't wear flats because I don't feel like they have good arch support, but you can wear flats with them.

Hemlines: exactly at the knee is the most flattering place for most people, and this is true for both pencil skirts and A-line. I think simple (no ruffles or extra crap) is best.

Contrary to advice above: do not wear sneakers in an office unless it's "casual Friday". Sneakers are not business casual; they are casual casual. Same with denim: Fridays only and only if your workplace as "casual Friday". Denim is not business casual.
posted by Kurichina at 12:53 PM on March 22, 2013

Best answer: Yea, boots. Cowboy boots or chunky low heeled boots are more casual (obviously) than high-heeled, sleek boots. Tights if winter, bare legs if spring or fall. If you have thin legs you could do those high socks that show above your boots with a shorter skirt. In summer with casual dresses and skirts I wear flats, sandals, or flip-flops. I personally detest leggings worn anywhere other than to work out, but it's "acceptable" to wear leggings under dresses. Ugh.

I find dresses and skirts WAY more comfortable than pants. A-line is always flattering, especially if you have hips/a butt. Thick jersey skirts with flat elastic waistbands (all of mine are maxi or below-knee, but again if you have thin legs you could go shorter) are super comfortable and can range from extremely casual to more cute/put-together casual. Jean or corduroy a-line skirts are good in fall or winter. Casual fabric will make a skirt or dress more casual. So cotton, denim, etc instead of silk or more flowing or embellished fabrics. (You can make those casual too, with jean jackets and T's and stuff, but that's slightly more advanced;-)

Check out this blog. She is about your age and wears dresses and skirts almost exclusively, and everywhere. Some of her outfits are quite dressy but some are not. I think it would be a good place to get ideas (or the courage to wear a dress walking in a forest) if you're new to skirts.
posted by DestinationUnknown at 12:54 PM on March 22, 2013

For me, opaque tights for winter, bare legs for summer. I am verrrry white.

Again, for me, tall boots in winter, ballet flats year round, sandals in summer. Something along the lines of Chuck Taylors or Toms is also a good choice. I feel like non-sandal heels dress up a skirt a lot, so that's not probably what you're looking for.

I think skirts are WAY MORE comfortable than jeans (unless it's really cold) and about equally convenient so I am maybe not the best person to answer this. Different people are flattered by different skirt shapes/styles. I find A-line knee-length-ish skirts to be the most comfortable and they look good on a lot of body types. Pencil/tapered skirts read dressier to me. Black skirts also read dressier. I wear nerdy t-shirts with my gray and brown A-line skirts but wouldn't do that with a black pencil skirt.
posted by mskyle at 12:54 PM on March 22, 2013

Best answer: -Boots, flats, or something like Toms or Keds will dress-down a dress or skirt.
-Look for jersey or cotton fabrics. Anything un-lined is a good bet for casual.
-Look for A-line or straight skirts, above the knee. Pencil skirts often read dressy.
-Jean jacket, cardigan, or something else structured on top.
-Hair up in a messy pony for casual; down for more dressy.
-Funky jewelry = casual, small delicate jewelry = dressy.
-Bare legs = casual, pantyhose = dressy.
-Opague tights or leggings = casual, sheer tights = dressy.

Basically, I live in skirts year-round. My uniform in the winter is equestrian boots, opaque tights or leggings, a fitted skirt, a cotton top, a denim or otherwise cropped jacket (like a fitted army jacket), a chunky scarf, hair up and messy, and big earrings. Summer is flats, bare legs, a flowier cotton a-line skirt (bike shorts underneath = no chafing), a tank or tee, maybe a scarf and a jacket or cardi.

In my experience the more layers you use, the more casual you will look.
posted by stellaluna at 12:55 PM on March 22, 2013 [2 favorites]

Best answer: Tights and leggings are both in! It's still freezing where I am, so I'm doing black tights under my skirts along with knee-high boots. I'm short, so my skirts are all knee-length or just-above, and my boots hit below my kneecap; if you're doing the boot-skirts combo, either there should be a recognizable gap between the hem of your skirt and the top of your (knee-height) boots, or the hem should fall low enough below the boot-top that they're not interacting awkwardly. As for bare legs, the only time I think they look awkward is if my personal perception is that it's too damned cold for bare legs, but my legs are medium in skin tone, so I'm probably not the right person to assess that aspect.

I pretty much wear any shoes with my skirts except athletic shoes ("plimsoll"-type sneakers, like Keds or Converse, work with most of my skirts for a casual weekend look), but most of the non-boot-weather time, it's flats or sandals.

As someone with a moderately-hippy body, I tend to go for A-line skirts that break at the knee. Simple solid-colored "tailored" cotton, like black or blue, or dark denim or corduroy. I like them better than pencil skirts, because I can still bike in them without worrying too much about flashing anyone (though I wear bike shorts underneath as a backup anyway); hell, I've even gone impulse-kayaking in them multiple times. I've also done this in more floaty girly patterned skirts made of some material that dries quickly in the sun, but basically, yes, as long as you can move your legs the way you're used to in pants, you can totally do skirts :)

In terms of "just going" with a t-shirt, though, a denim, dark cotton or corduroy straight skirt (read: no pleats) is your best bet for being "not pre-teen" yet also "not overdressed."
posted by Pandora Kouti at 12:56 PM on March 22, 2013

Best answer: I'm like you in that I am an inveterate jeans-wearer, wanting to kick my style up a notch, but still often feel too dressy in skirts. A great casual skirt in my mind is something sold by an "outdoor" or "travel" clothing line such as REI, Athleta, or Ex Officio - A-line, stretchy knit, length to just above the knee, and sometimes they even have a hidden pocket, which is helpful if you are not used to wearing pocket-free "feminine" clothes. Here are a couple of good examples.
posted by matildaben at 1:00 PM on March 22, 2013 [1 favorite]

Best answer: When I started wearing skirts/dresses every day, I wore them with some chic combat-style boots and black tights. In the winter I pretty much stick to black tights underneath (like Zooey Deschanel, who says black tights are her security blanket). That was my tomboy transitioning phase. In the summer I wear no tights and a pair of tiny black spandex shorts, so I'm not self-conscious about my skirt blowing up in the wind.

A-line skirts were my first love, now I wear those and pencil skirts. H&M had skirts last year that were just like a loop of stretchy fabric, like a tight black miniskirt, but not prone to riding up or anything, they were pretty cool as something you could just slap on underneath a casual blouse and sweater. T-shirts go well with a pencil-style denim miniskirt, imo. Tall black boots-- also I wear brown leather ankle boots + boot socks with both with black tights and bare legs and it's my current favorite look. I also have a few pairs of wedges-- espadrilles and some t-strap velvet black wedges. ModCloth, H&M, Ruche, and Target are good places to shop for our age range and what sounds like your style.
posted by stoneandstar at 1:02 PM on March 22, 2013

Also my favorite comfy look when I stopped wearing jeans every day was an above-the-knee length cotton a-line sundress with pockets. Pockets really help the impression of security.
posted by stoneandstar at 1:03 PM on March 22, 2013 [1 favorite]

The skirts Athleta sells are casual and comfortable and would work fine with a t-shirt with writing on. So would denim or khaki skirts from the Gap or Old Navy.
posted by Sidhedevil at 1:03 PM on March 22, 2013

Oh, my latest thing is that those really billowy blouses are in right now-- to be worn with skinny jeans. But I buy them and wear them with skinny jeans and with high-waisted skirts (usually a-line, above the knee), and it opens up so many cute vintage styles.
posted by stoneandstar at 1:05 PM on March 22, 2013

I've been trying to do more dresses and skirts at work. Old Navy has a lot of casual stuff (both hanging-out casual and business casual). I wear this skirt in either black or gray, with tights in the winter and bare-legged in the summer. (I'm plus-sized, but I'm betting they have a similar skirt in smaller sizes too.) Throw on a nice knit top, and maybe a light cardigan, and I'm good to go. Sandals in warm weather, flats in cold.
posted by sarcasticah at 1:08 PM on March 22, 2013

Best answer: Rocket Dog flats for me, they are the best shoes in the entire world and they look amazing with casual dresses.
posted by lydhre at 1:09 PM on March 22, 2013 [2 favorites]

BC Footwear has a TON of supercute, casual/dressy shoes. They're a little on the expensive side and the fit can be odd so I would try to try them on in person whenever possible.
posted by stoneandstar at 1:14 PM on March 22, 2013

What's your figure like? Not every skirt works on every woman.

I wear mostly skirts, formal and casual. Generally speaking it's all how you dress it. Usually I pair mine with cheap ballet flats and legs like pair of dumpy alabaster columns. This is not a fashion mistake in urban Canada.

In cold weather it's basically black tights, though leggings (you can pair them with socks) present another alternative. Bare legs are in right now because nylons do diddly for anyone other than cost money.
posted by Phalene at 1:16 PM on March 22, 2013

Best answer: I live in skirts in the summer and dresses half the time in the winter.

What do you wear under them?

Tights-- usually thick cotton in the winter. I own a lot of black tights and also gray tights, which are a better neutral for some colors.
Running tights-- especially in the deep of winter.
Pantyhouse-- if I forget to shave or if I have some sort of actual meeting.

Can you do bare-legs if your skin tone is somewhere between ivory and glow-in-the-dark?

I am glow-in-the-dark and I wear bare legs proudly.

What is the deal with shoes? ... How do you know what shoes to wear with a skirt?

Generally my criteria is more "what shoes go with my job, which is to say, lots of boxes and dusty books" and then I figure the skirts will work themselves out. I sometimes wear converses with skirts and dresses; I wear knee-high boots all the time; ballet flats a crazy amount; pumps if I am feeling fancy. I try to wear flats if the skirt is on the high side, and I wouldn't wear converses with a more suit-like or fancy dress. Seychelles are often nice and often on sale. Also, Lands End.

What kind of skirts are flattering, comfortable, and casual? Is there anything out there that matches the convenience and comfort of jeans?

Oh god yes. In the winter: SWEATER DRESSES! Like wearing a blanket. A fancy-seeming blanket. Way easier: throw on tights, throw on dress. Add boots. If fancy, add a belt around the middle and/or a longer shirt with sleeves (depends on dress.) Jersey dress? Rinse, repeat. Throw on a black blazer if you want to mix it up.

I know I recommend Lands End all the time, but I think they have a very good mix of wearable fabrics. The jersey cowlneck dresses are fantastic; I actually own two. They're substantially easier to put on and wear than pants are. Do not get anything with tiny pleats if you don't feel like taking care of tiny pleats and dry-cleaning.

BONUS: are there any skirts that look okay with nerdy printed t-shirts, without being too pre-teen?

I have a flared, sewn-in pleated jean skirt that I wear with Achewood shirts with pride. I think a pencil jean skirt would also work well. Plain color cotton skirts (A-line or circle?) would also do just fine.
posted by jetlagaddict at 1:18 PM on March 22, 2013

Best answer: More things that will make an outfit with a dress or skirt read more casual: a canvas tote bag instead of a leather bag. Jewelry - less shiny gemstones and more "earthy"-type stones, pendants on leather/silk cords instead of gold, minimal jewelry, totally non-serious jewelry like a knotted rope or friendship bracelet. A jean jacket, as I said above, or a cotton khaki jacket with lots of pockets or zippers, or a long cardigan. Long scarves and maxi dresses and skirts are (provided they're not actually dressy) casual almost by default. They're just too bohemian-looking to be "proper" office clothes.
posted by DestinationUnknown at 1:25 PM on March 22, 2013 [1 favorite]

I have a gored skirt like this one, except without a bow, and it looks great with t-shirts. I pull it up so it's knee-length and wear the shirt un-tucked.
posted by muddgirl at 1:25 PM on March 22, 2013

In the winter, I am a jeans-only lady, like you.

But in the summer? Ohhhhhh, shit, it's on with some dresses and skirts! I am not fancy and I don't ever feel weird in my summer attire (and I am prone to feeling weird when dressed up so let this emotion speak to the fact that it's possible to wear non-pants without feeling like you're going to the prom). I stick to long dresses with some flow. They feel less dressy to me but I think short dresses work, too.

Hippy-ish skirts and dresses are my go to with either flip flops or flats. Old Navy does have some pretty casual get-ups that fit the bill and I always find cute long dresses at Target as well. American Eagle and aerie always have a great selection -- for those, maybe see if you don't have a Factory Connection store or something similar in the area. I've only ever paid full price for one AE dress because I generally get them for less than $15 at a Factory Connection store. Likewise, an outlet mall, if there's one near you as well, is great for picking these pieces up on the cheap. The skirts I wear usually look best with just a plain solid tank top as well so that tones down the Dressed Up Factor...
posted by youandiandaflame at 1:29 PM on March 22, 2013

Best answer: I wear a lot of skirts and dresses, to the point where a friend mentioned, after I arrived early to a group get-together, "I saw a skirt out the door, I knew you were here."

If it's warmer, I always wear some sort of shorts under my skirts and dresses (usually biking shorts, but I also have a pair of lace boy-shorts that work better under more form-fitting things. It's a habit that starting from wearing lots of dresses when I play with my band and while lugging equipment around, bending down to plug in cords, I didn't want things showing that I didn't want to be seen). The rest of my legs are bare (and yes, I too am very pale). In the winter, tights or even skinny jeans.

You can wear sneakers with skirts or dresses! Maybe not running shoes, but Chucks or something less clunky, definitely!

I've worn denim skirts with my Batman t-shirts. Like jeans, jean skirts will go with almost anything. Mine is a basic shape, not even a-line, more like a tube skirt, but denim.

One way to wear dresses casually is just to add casual accessories to less-than-casual dresses. I have two examples of this: 1.) I bought a shiny gold strapless 'clubbing' dress for my birthday one year. Wore black strappy shoes, dangling necklace, wrist full of bangles. Not really something you would call a "work" dress by any means. BUT - I have indeed worn it to work as well as out and about to lunch on weekends, etc by taking the dress and adding skinny jeans, combat boots and a black blazer over it. MUCH more casual, though it was not a casual dress. 2.) Bought a navy and white polka dot dress in a silky fabric to wear to my boyfriend's cousin's wedding. Paired it with red wedges, a simple pearl necklace, everyone gave me many compliments. Repurposed the dress to wear at punk shows by adding a kelly green cardigan and kelly green high-top Converse.

Loose dresses (think cottony, billowy sundresses) are often more comfortable than jeans, plus it makes getting dressed so much easier--your top and bottom already match!

Anything works, really, if you wear it with confidence.
posted by dearwassily at 1:36 PM on March 22, 2013

Title Nine and Athleta both carry dresses+skirts in a range of formalities. Many with pockets (yay pockets).

I find any kind of tights terribly uncomfortable so I get thigh-high socks for the winter instead- sockdreams has these (be sure to read their reviews to ensure the tights you get will actually go up high enough, unless you like having bare knees. I don't like that.)

As another woman with sizeable hips, I'd vote for A-line. Pencil skirts fit me better than pants, but A-line are more made for my body shape.

I'm not a shoe fashion person, but I go with mary-jane style or clogs in the winter, and sandals in the summer. Ziera makes a mary-jane style that's very comfortable.
posted by nat at 1:53 PM on March 22, 2013

Invest in a pair of amazing casual boots that you love. For me it's Frye Jane Stitch in Redwood (pricey but will last a lifetime. Yes, like 25 years.). I have a black flat pair, too, and slightly shorter heeled tan suede pair.

I wear them with tall socks that just peek over the top of the boots (extra casual) or with tights (smooth black or thick knit gray or navy, plus socks).

No leggings, yuck. That's sort of a college-girl look.

In warm weather, skirts with bare legs and leather flats or boat shoes.

Fabric makes them casual, too - linen or cotton, instead of something more expensive. Bright colors and prints.

On the top? Whatever you'd wear with jeans.
posted by amaire at 2:07 PM on March 22, 2013 [1 favorite]

To look more casual | To look more dressy

Matte fabric | Shiny fabric
Stretchy fabric | Woven fabric
Patterns | Solid colours
Earth tones | Jewel tones
Opaque tights | Sheer hose or bare legs
Smooth jewellery | Twinkly jewellery
"Heavier" footwear (boots or flats) | Delicate footwear (heels)

Kate Middleton's shiny blue wrap dress is pretty dressy, especially with bare legs and heels.

A matte jersey dress in a pattern, with tights and boots, looks much more everyday-appropriate, even though the actual shape of the dress itself is not that dissimilar to Kate's.
posted by pseudostrabismus at 2:20 PM on March 22, 2013

Maxi dresses and Toms shoes! Here is a picture of me (on the left) in a super casual maxi dress. I was even able to wear a sweatshirt and leather jacket over it.
posted by kbennett289 at 2:24 PM on March 22, 2013

Also, try this website for some great variety.
posted by kbennett289 at 2:37 PM on March 22, 2013

As to the graphic tee question - you can definitely do a t-shirt with any basic casual skirt (knit, cargo, etc in a neutral color), but I personally really like the contrast of a graphic tee with a more feminine bottom half - a la Alexa Chung here.
posted by celtalitha at 2:50 PM on March 22, 2013

And here's a recent blog post about the trend, which I didn't know was a trend, but hey, all the better!
posted by celtalitha at 2:53 PM on March 22, 2013

Best answer: I just bought two of these dresses (black and grey) because they are super easy to wear (and I'm previously a jeans and only jeans on non-work days kind of person). I've been wearing them with sneakers (cons style ones) or ballet flats (a white pair with retro details from TUK). Knee high boots come winter but I'm probably going to get a pair of the combat or cowboy inspired boots that are around right now for the end of wet season (hot but the ground/grass is wet enough to soak any shoe that isn't a boot, and aircon is up high enough that it's vile for the rest of the day). I like that dress because it's effectively an oversized shirt but not ill-fitted. I do wish it had pockets but I'm going to get a wristlet for those days I'm not already having to carry a bag. I also have a similar dress I made but the fabric is more poly than cotton so it feels a little dressier. My other standard dress is a Drape Drape one I made and it is weird enough to be casual with cons and a cardigan, but I could wear heels and wrap and make it swankier AND I can wear it as a really lovely shirt.

Skirts have been harder for me. I have a bunch of black pencil skirts and that's about it. None seem to fit well apart from the pencil skirts. I quite like graphic tees with midi skirts as well, and a pair of ballet flats. I haven't found myself a decent midi skirt (or made one) but they are more likely to have pockets. I tend to wear my graphic tees with a pencil skirt and ballet flats/cons.
posted by geek anachronism at 3:03 PM on March 22, 2013 [1 favorite]

What do you wear under them? If it's too cold for bare legs, I wear tights and tall boots (sometimes ballet flats if it's not all snowy). If it's quite cold and I'm also too lazy to wiggle into tights, I will wear leggings with short skirts and boots but it's not my preference. If it's warm enough, I do bare legs. I am pretty fair, but a) all skin tones are valid, even if they're not considered the ideal, and b) a few days of even a bit of sun exposure will take the edge off the "glow-in-the-dark" effect. I know a lot of people wear cropped leggings with skirts but I just don't like it much. I do have a pair to wear as one solution to avoiding exposure while biking in skirts, but that's it.

What is the deal with shoes?
Boots an option unless summer. Ballet flats and sandals, chosen according to what matches color-wise. I have some sneaker-like shoes that are shaped kinda like ballet flats and I can wear those if ultra-casual, otherwise I never wear sneakers with skirts because I can't pull it off.

What kind of skirts are flattering, comfortable, and casual?
Knee length, flowy or at least not tapered. I think fuller skirts change the most with just an inch or two above or below the knee in terms of looking youthful or more...classy? chic? Or dowdy, depending on the skirt. I wear knee-length dresses with other tops over them a lot which is actually more comfortable than my skirts sometimes because I almost always wear layers on top anyway.

Is there anything out there that matches the convenience and comfort of jeans?
In my opinion, not quite, but close, with tradeoffs. Skirts give me less annoyance around the waist and fewer fit problems, but I either have to deal with tights, or find a chub-rub solution. Which you didn't ask about, but I've had the best success with the Monistat chafing gel (sold near their other products but not for yeast infections and not sold everywhere), and some with Spanx but they're a pain. Some people say cheapie "bike shorts" work but they always ride up on me.
posted by zizania at 3:10 PM on March 22, 2013

Oh, I wear either bike pants, boxers or cut off stockings/leggings under my skirts for chubrub solutions.

I am rapidly finding a dress more comfortable than jeans, primarily because I've finally found dresses that fit. The only jeans I have that don't fall down/show my butt crack are a pair of super-retro highwaisted ones (which tend to be even dressier than my dresses). Every other pair cannot cope with my thigh/hip/butt-to-waist ratio. So getting through the day without having to hoik my paints up is almost enough to outweigh no pockets. There is no breaking in of skirts, no stretching out effect the way there is with jeans. They are more forgiving of the monthly fluctuations in my weight. BUT they tend to not have pockets, require that layer underneath if your thighs rub/it's cold, and can be a bit harder to match shoes. But once you're over the 'oh god dresses = dressy' hump it's kinda nice.
posted by geek anachronism at 3:23 PM on March 22, 2013 [1 favorite]

For under skirts, I recommend tap pants. I have a pair of silk ones from Victoria's Secret a long time ago. They function as a slip to prevent clinging and help preserve my modesty in case I forget I'm wearing one and bend over.
posted by mlo at 3:25 PM on March 22, 2013

Best answer: I always recommend Nordstrom's personal shopper service to anyone who is trying out a new look or needs a new wardrobe. It's a free service, and they will work with a budget and won't steer you to designer labels (unless that's what you want).

I'm mentioning Nordie's personal shopping service because if you want to go the skirt route, the key is to find a style that flatters you - and skirts are so individual that even if you were to give your height and build I'd be hard-pressed to tell you a hard-and-fast rule of what to wear or what not to wear. The only thing to do is take a morning or afternoon and try on lots and lots of skirts and see what fits and flatters. The personal shopper really comes in handy here! They know where to hunt down things you might never have thought of - thanks to the one personal shopper I had, I now have a closet full of lovely abstract 60's style prints because I fell in love with a dress she found.

I myself find that I can wear certain maxi-skirts - which ought to be a no-no on a petite woman like me - as long as they are sized for a petite (not an average-sized woman) and are of a nice floaty cotton or chiffon fabric. These floaty maxis make wonderful casual attire. I pair them with a top that skims my body so no-one can see my waist (I'm extremely short-waisted), sandals, and my favorite handmade jewelry, a sweater if it gets chilly, and I have a terrific outfit for a casual workplace or an outing.

For winter, I like pencil skirts with tights and ballet flats, a knit top that again hides my waist, heavier jewelry, a cardigan, and I have a good winter business casual or a bit dressier outfit.

In general, heavier wools, silks and lined linens are dressier; cottons, denims, light linens and anything floaty on the one hand or rugged textured (like corduroy) on the other is more casual. Footwear that is not a pump or slingback dresses down an outfit - think boots, ballet flats, sandals, etc. depending on the weather and your office.
posted by Rosie M. Banks at 3:40 PM on March 22, 2013 [1 favorite]

If for any reason you're uncomfortable going with bare legs there's leg makeup you can get at the drug store - you spray it on and rub it in, and then wash off at the end of the day. Not spray tan.

Denim would definitely work with a fitted nerdy tee. Also look at this (note the shoes with it).

You Look Fab has some advice on pairing skirts and tops. Also check out the related posts on the left. Academichic is mostly defunct but has a lot of images of outfits based on skirts and dresses that you may find inspirational.
posted by bunderful at 3:46 PM on March 22, 2013

In the winter it's tights and boots. I really don't like the look of tights and flats together. In the summer I don't wear anything but chones under my skirts. When I had bigger thighs and chafing issues I would wear spanx that were several sizes too big. There's also silicone based anti-chafing gel if that's an issue for you.

Shoes: Boots, flats, flip flops, sandals of all types. I'll even wear skirts and Keen sandals. But I think you have to live west of the Rockies to get away with that.

And I am a firm believer that a straight denim skirt goes with everything, ESPECIALLY nerdy t-shirts.
posted by elsietheeel at 3:53 PM on March 22, 2013

My wardrobe's "dresses to jeans ratio" is currently 20 to 1. Seriously. I wear dresses because I'm a lazy mofo who can't be bothered to think of an outfit in the morning. Dress + cardigan and then I'm out the door. Half my dresses have some kind of collar or button action, which adds to the casual vibe. My favorite dresses are vintage-y print wrap-wanna-be dresses with v-necks (note, these do not actually require wrapping because that is way too much hand-eye coordination in the morning for me).

As for skirts, I'm going to recommend you also pick out a few brightly colored patterns in addition to neutrals/denim. I have a orange/baby blue/pink blobbies on a navy blue background skirt, purchased in the 1990s! (my god, that skirt is probably of drinking age!) from The Limited and I invariably get compliments on it. Patterns on bottom usually lead me to choose neutrals (brown, ivory) on top but then I get cold and add a brightly colored cardigan on top of that.

Other things to consider:
- A good half or full slip (or slippery bike shorts) so the more staticky fabrics stop riding up the thighs when wearing tights.
- Nthing boots. I did knee-high for most of my twenties, as well as some crazy spiral non-matched boots from Campers that totally cramped my drama when I wanted to storm out of the house because they took ages to put on.
- Discount stores like Ross or TJ Maxx are good places to try on dresses. I think 10 out of my 20 are from Ross.
posted by spamandkimchi at 4:11 PM on March 22, 2013

Best answer: Oh god yes sweater dresses. It's lovely, you feel like you're in comfortable pyjamas all while knowing you look classy enough for the office.

Indeed, anything out of jersey, cotton, or linen will read as more casual. Just one word of caution with jersey dresses: if you buy online, be very careful to look for any and all signs of them being so sheer they're see-through. Mainly you can tell on real women by looking, ahem, through the legs (if you can see crisp, clear leg shadows, it's probably too sheer), or on mannequins by looking at the, well, rear end. If you can see a mannequin's rear end through the fabric, it will be even worse in real life.

What do you wear under them? [...] What is the deal with shoes?
Nthing boots! I also like wearing tights and office-appropriate Mary Janes with a bit of a heel.

In warmer weather, ballet flats are great and of course sandals. I wear fancier Birkenstocks to the office, but here in France that's fine; I know in some places in the US they have a stronger casual read. (I'm originally from Oregon so I kind of feel like I'm hiding in plain sight when I wear Birks to the office... grew up wearing tattered Birks around Eugene, where they read quite differently than in France.)

In warmer weather I don't wear anything on my legs, and I too am a hairy alabaster. egads I really am Eugenian...

What kind of skirts are flattering, comfortable, and casual?
Indeed, A-line skirts work on most figures. With less flare they can look nearly straight; I love longer ones (mid-calf) over boots in winter, very classy. Knee-length for the office is good, and slightly above, too, if you can pull it off. (For instance, at 5'11" I'm tall enough that something that hits two or three inches above my knees looks like a mini-skirt, so I tend to be conservative.) This summer I'm going to try what are called flared skirts, nearly a 1950s silhouette; you'd almost need an underskirt to keep the volume, but not quite. Really versatile, and flattering on most silhouettes.

Is there anything out there that matches the convenience and comfort of jeans?
I'm going to sound like a broken record given how often I've said this in comments here, but ever since I started sewing my own skirts – you only need basic sewing skills to whip up a flattering A-line skirt – I will never, ever go back to anything else. This winter I practically lived in three skirts I made: a grey wool blend that was warm, soft, comfortable; a cotton one with a black background and understated plum, green and reddish waves that matched several blouse-like t-shirts; and a more fun purple skirt with huge pink plum blossoms on it when I wanted to imagine winter was less dreary. I wore that one with crisp white blouses and shirts. Just today I was peeved when I realized all my wintry tights needed washing and it meant I had to wear jeans: "ugh, I wanted to wear my wool skirt!" It goes great with nerdy printed shirts, btw. Wool is one of those fabrics that can so easily be dressed any way you like. Any solid-color skirt would be good with a printed tee; it's mainly the cut and fabric that will set the skirt's (in)formality.

Count me as another woman who feels paradoxically liberated by stereotypically "feminine" dress. I never wore dresses or skirts until a few years ago, had been a tomboy in school; now I hardly wear anything else. Cotton sundresses are absolutely wonderful in summer. (I too wear boxers or equivalent beneath in hotter weather.)
posted by fraula at 4:11 PM on March 22, 2013 [1 favorite]

Best answer: My weight has fluctuated a bit recently, and skirts have been a life saver. Pants that hang a few inches lower get caught in my shoes, higher and they make me feel like Urkel. Changing skirt length isn't so dramatic.

I wore a bright pink linen A-lone skirt today with a silk shell and a black cardigan plus black pumps. To dress it down I would absolutely wear a plain tee and brown strappy heels (I snagged naturalizer Lailah for $20 in my weird size off season!). I don't wear graphic fees except for one from a now defunct favorite band and a purple one that's sheep wearing sweaters. Those shirts I wear with a denim pencil skirt (I own two, one almost black, the other a smudge lighter. Yay Goodwill!) or a linen skirt and I throw a jacket over the mix. My favorite for a few years is a seersucker one. Which is a radical I am seeing everywhere right now. It's like people finally figured out that southerners know how to do summer!

Most of my clothes are from Thrift shops and clothing swaps, which allows me to sometimes go a smudge out of my comfort zone. Though jcrew has a red pencil skirt, will end of season. I would kill to own it. I would wear it with everything and in all weather for I know the magical properties of wool. And red.

Shoes and jewelry are going to be the deciding indicator(s) of your formality unless you're wearing satin head to knee. Shoes have been well covered here already, so I'll just chime in to add: be comfortable. Beauty over comfort is bullshit and I am constantly glad I learned that early despite vigorous attempts to teach me otherwise. My black pumps are naturalizers because A) I can afford them and B) they are reall fucking comfortable. I can wear them with jeans and a tee and be perfectly casual. But they're a by trickier with skirts, as peoe have pointed out.

Wearing things under skirts, I started doing that this winter because I can't handle being cold. Sweater tights. Bought two pair on clearance in odd colors/patterns. Hand wash them to preserve their looks. And a pair of regular purple tights (in America Tigre are different from nude pantyhose), again, on clearance. 2 more pairs would have. It down on laundry/ allowedme to wash them All Together once a week. Leg Warmers. I knit, so I made a pair. Why had I never done this for myself before? Why only as gifts for other people?!?

I am also pale and do not shave. When the weather is warm I wear nothing under my skirts except underpants. (I spend my razor money on tights and ice cream!) Nobody ever remarks beyond the occasional body policer doing me the favor of alerting me that I don't want them in my life.
posted by bilabial at 4:45 PM on March 22, 2013 [2 favorites]

I pretty much live in skirts in the summer, because it is hot where I live. I get too chilly in the winter and really dislike tights, but in the summer I'm pretty much always in a skirt.

Personally, I shave my legs every day in the summer, because it is really fast if you do it all the time and I am not comfortable going out with stubble or leg hair, but YMMV there. If you are squeamish about it like I am, this is a good way to handle that. If you're not squeamish about it, power to you. Hairy legs are totally fine.

An important tip for skirts/dresses that I read once that really holds true is the one-inch knee rule: the skirt should fall an inch above your knee or an inch below your knee. I'm short, and I find this to be very important. Obviously it does not apply to minis or maxis, but that in-between length needs to fall right.

Your body shape is going to determine what skirt looks best best best on you, but an A-line skirt is the most forgiving for any body type. I'd get one in a dark color, like black or navy or grey or olive. That will take you far. If it's a nice, high-quality cotton you can wear it year-round and it will look cute with nerdy tees and can also be dressed up with a proper blouse.

I have a pair of pewter Cole Haan shoes that are perfect with skirts or jeans. They have a bit of a heel, which is vital for me, but ballet flats look super cute on other people and are usually inexpensive and are great with skirts or jeans. In the winter, as other posters have covered, a skirt looks fabulous with a pair of boots.

Happy skirting! :)
posted by k8lin at 4:55 PM on March 22, 2013

The best skirt/dress advice I ever had:

The shorter the skirt, the flatter the heel.
posted by citygirl at 6:34 PM on March 22, 2013 [1 favorite]

For those of you who wear tights: doesn't it get expensive? I feel like I wear holes in the heels after just a few wearings.
posted by The corpse in the library at 6:35 PM on March 22, 2013

I think it depends-- I have some thick tights that I've had for three+ years now that are going strong, and I've ripped some of the delicate ones after three hours (sad times.) The Marks and Spencer's black opaque ones have been genius and I haven't found anything at that price point in the states. DSW has great sales on tights.
posted by jetlagaddict at 8:41 PM on March 22, 2013

I love tights. I have a whole collection of tights, many from Sock Dreams, and skirts are my excuse to wear tights as much as anything else.

Skirt or dress plus tights plus boots is as casual or fancy as you want them to be. For me, more casual skirts/dresses are ones in stretchier/flowier fabrics, i.e. less tailored, with dark, solid tights, and flat boots. More dressy is a more tailored outfit, with lacier or sheer or fishnet tights, and heels. I live in foggy San Francisco, so I can rock tights pretty much all year long, but for those rare hot days or when I visit warmer climes, I just go barelegged, with sandals or heels.

To the corpse's point, I often wear socks over my tights and under my boots. That may make a difference?
posted by gingerbeer at 9:37 PM on March 22, 2013 [1 favorite]

I buy tights at Ross/TjMaxx/Marshalls/clearance. I have never paid over $8 per pair, usually more like $5.99 for a two-pack. The "retail" standard price on the things are insane, especially for good quality. If you know you'll wear them next fall, stock up in the spring!
posted by celtalitha at 10:27 PM on March 22, 2013

I live in an Orthodox community, so while I am no source of advice on anything to do with fashion, I do know a little about skirts every day.

Go to Goodwill and find a standard black skirt that you like. Maybe this is A-line at the knee, maybe this is ankle-length, whatever. For this particular purpose I say go with a synthetic. (Cotton is great for disposable clothes, but skirts DO RIP and the butt will pill.)

THIS is now your pair of jeans. You can wear it with whatever you wear jeans with. When it wears out, you can buy a duplicate of it.

This is not to speak of fun clothes, dresses, etc., which I also like--only to explain how a skirt is NO DIFFERENT than jeans.
posted by skbw at 1:57 AM on March 23, 2013

Best answer: I live in dresses with boots. I am kind of dreading when it will be too warm to wear my leather boots. I wear a lot of tights and surprisingly, they don't rip too often. I get the Hue brand at Macy's usually, almost always plain black - it sounds boring but then I know they go with everything. The nice thing with wearing boots is that you can hide a lot of holes. Most of the holes I get are in the toes which is not a problem with boots. I bought a few new pairs of tights this season and one is still in the package. I haven't gone bare-legged in a while because it's been cold. I usually save that for warm weather.

I was reading on xojane about how to pack less when you travel and one of the suggestions was dresses, which made me think, yes, and? Dresses are the best. It's like an adult crotch-less onesie. You put it on, grab some shoes and you're *done.* Scarf, necklace, earrings, tights = bonus. I've gone up and down a few pounds recently and right now, I can't wear most of my pants. This is a non issue with my dresses and skirts. And I don't spend a lot of money on dresses either - most of the dresses I buy are from Target or Gap. Plus, I think it's a lot easier to look cute, pulled together and memorable in a great dress than a pair of jeans.

I hate to say that I came late to this party but you might want to consider a slip. Most of the time, especially when I'm wearing tights or a dress with a lining, I can get away without one but I usually wear one just because I want to look nice at work. I'm a recent convert and I bought one because I went to work one day wearing a dress I love without tights and it just kept clinging to my legs. I don't know if it was because I hadn't shaved or what but that dress was all up my butt. I went to the Macy's near my office, bought one slip and it saved the day. Since then, I have bought one other slip. To recap, I wear dresses or skirts to work almost every day and own two slips.

I just don't feel like I'm dressy when I'm wearing boots. I feel like a badass in a dress, which apparently is how I like to feel :)

Now can someone explain to me how to wear pants?
posted by kat518 at 8:44 AM on March 23, 2013 [3 favorites]

When I was your age (10 yrs ago!), I wore a lot of graphic tees with a corduroy skirt (above the knee) and my puma flats. In the summer/really hot weather, I subbed it for a cargo style skirt that looked a lot like this (that's a skort, but you get the idea). I currently buy a lot of casual skirts and dresses at Ann Taylor LOFT, the gap, old navy, and stores like that. Come to think of it, a lot of the short, casual skirts I have from back then and now are all from LOFT.

The puma flats are seriously the most versatile pair of shoes I own. I love them and wear them all the time, I think I'm on my 4th pair at this point. They don't really work in the winter with tights (just wear casual flat boots then), but will work at all other times.
posted by echo0720 at 9:18 AM on March 23, 2013 [1 favorite]

Oh, also, I only recently (like in the past 4-5 years) started wearing tights. Before then, I would suffer (and wear spanx under my skirt and tall boots to keep warm). In hindsight, that was dumb, but I also don't think tights were as in 4-5 years ago as they are now. It is much easier to find cute tights now in all sorts of colors and patterns.
posted by echo0720 at 9:20 AM on March 23, 2013 [1 favorite]

Helpful hint: if you find that your tights/stockings constantly get holes in them, check the insides of your shoes to make sure there are no rough edges or protruding bits. Run your hands around the insides and if you find a rough bit, cover it with sports tape, or stick-on gel cushioning if you want the padding. I once destroyed a pair of heavy cotton tights because I wasn't aware that I had a rough spot on the inside heel of my shoes (which otherwise were in pretty good repair). A bit of sports tape fixed that.

Then make sure your toenails are well groomed and filed. Sharp and/or jagged toenails can cut through tights like a knife through butter. Clip, file, and your tights will thank you.

With a little care, I've had tights (the opaque kind, that is, not the pantyhose kind) last for years; I've only had to toss them when they've faded and shrunk, not when they've gotten holes in them.
posted by Rosie M. Banks at 9:56 AM on March 23, 2013

Good eye, kat518. I didn't notice the omission of slips.

For many years I declined to wear a slip (extended rebellion from my mother's teaching). But to paraphrase the Jewish grace after meals, I used to be young, and now I am old, and I have come to understand that the slip REALLY DOES make the skirt hang better. Also, as for light-colored skirts, where I myself am a commando offender, YES, EVERYONE KNOWS that you're not wearing a slip.

Vanity Fair is a good brand.

As for skirt attitude--I see from your history that you were in the upper South at one point. Are you from the South or Midwest? Do you have any super-hardcore older relatives (female, LOL) who lacked a girly personality but wore skirts because pants were just too far out? Take a look at this (live footage) of Maybelle and Sara Carter. They're not doing gender performance...this is just their default attire. As it happens, my own great-grandmothers were straight-up rejecters of skirts and wore pantsuits like this lady. But as you can tell from the pantsuit lady's song selection, she's already a generation younger than Maybelle and Sara. This "ladylike" thing is just a trip people are trying to lay on us. Enjoy your expanded wardrobe!
posted by skbw at 9:57 AM on March 23, 2013

Others have given great advice. I just want to mention that I like to wear ballet or Mary Jane flats with casual skirts and dresses in the summertime. Clarks makes great ones, in my experience. Flat sandals are also great.

Thigh rub is the only real downside of wearing lots of dresses/skirts. I'm still looking for a good solution. Usually I end up wearing bike-shorts style shapewear, because that's the only bike-shorts style underwear I can find. But I don't always like having the thickness and compression of shapewear. If the skirt/dress is unlined, shapewear basically necessitates a slip, or the fabric will cling really weirdly. Sometimes shapewear plus slip plus skirt is just too hot in the summertime.

This year, I'm planning to buy some culotte slips, AKA pettipants -- essentially slips in skort form. They seem surprisingly hard to find; I'm definitely going to have to order them online.
posted by snowmentality at 10:06 AM on March 23, 2013

I'm late to this party, but I have life-changing advice (it was for me, anyway):
If you wear tights, wear a pair of underwear outside of them.
I hate having to hike up tights (which happens regardless of fit), and undies over top of my tights keeps the crotch from heading toward my knees all the time.
I wear skirts and dresses 95% of the time, and where I live it's freezing cold for much of the year, so fleece-lined tights are part of my daily uniform (usually footless ones worn with boots and socks--which minimizes wear on the toes--but if I'm wearing shoes, then maybe tights with feet). The few times I haven't had outer-underwear, I've regretted it all day.
posted by Edna Million at 10:40 AM on March 23, 2013

Best answer: I never wore skirts until I moved to a new town ... I felt they weren't my style, they weren't casual! I felt shy about looking like was trying to look good, but I wanted to look good!

So I got over that. I checked my perceptions of other women who wear cute outfits. I usually don't think "she's overdressed," I usually think "I like that outfit a lot. She looks great."

Dresses and skirts do generally seem dressier in general to me though so I have some personal habits to keep it more casual:

- Never wear dressy shoes with them (I like ballet flats, boots, or casual sandals)
- Keep makeup casual - no heavy "evening" looks
- Wear opaque, not sheer tights or pantyhose (and sometimes in colors other than black)
- No shiny metallic jewelry

If you're not sure what kinds of dresses and skirts can be casual, I'd actually suggest looking at the selection at Target -- not necessarily to buy, but they've had a wide range of casual dresses lately and that might give you an idea of possible cuts and fabrics. I actually prefer dresses to skirts because I don't have to think about pairing pieces together (oh no what if the shirt I want to wear with the skirt is dirty).
posted by Kutsuwamushi at 11:39 AM on March 23, 2013

I've been wearing jean, cargo and above-the-knee straight skirts with tights in winter, and with the same tops I'd wear with jeans or with sandals in summer and whatever I'd wear with shorts. With pleated or full skirts, I often wear a cotton cardigan or layered tees. In summer, I wear Tevas and other comfortable sandals with everything. In winter, tights & boots. I especially like wearing a black sweater, skirt and boots, and bright teal tights.

Some people seem to need to comment on any change. Don't let it bug you; express yourself.
posted by theora55 at 11:42 AM on March 23, 2013

For those who struggle with chafing or "chub rub," runners use Body Glide though there are several similar products. I bought something by BandAid last year. I think Gold Bond might make a version. It should work all day. Body Glide looks expensive but one stick will last for a while.
posted by kat518 at 12:24 PM on March 23, 2013

What kind of skirt shape are you wearing? Personally, I much prefer knee-length A-line skirts that let me sit and slouch around however I like, which isn't possible in pencil skirts. Fabric matters too: cotton is casual, silk and satin is dressy.

Shoes: in winter, I wear flat, tall boots (can be difficult to shop for depending on your foot-size to calf-width proportions, but worth persevering) with opaque tights, often in fun colors like purple and red. In summer, I wear flat or slightly heeled wedge sandals. In spring and fall, go for flats: ballet flats, Toms slip-ons, even COnverse sneakers. The latter two will do wonders for dressing down a dress/skirt.

I will wear a printed graphic tee with any of my skirts. A slightly slouchy fit works well over a pencil or mini skirt (structured straight silhouette, try a denim pencil if you want to stay casual); a shorter tee or a slightly scrunched longer tee paired with an A-line or full skirt.

If you're used to wearing jeans, keep an eye out for skirts and dresses that have pockets. They're hard to find at lower price points, but I LOVE pockets.
posted by serelliya at 4:19 PM on March 23, 2013

You don't need body glide or special products. Cheapo solid antiperspirant/deodorant works a charm on the thigh rub. Very handy.
posted by lemniskate at 6:07 PM on March 23, 2013

I always had trouble wearing my dresses and skirts on a regular basis until I got a good pair of boots. Find one that you love and that will also look sexy with your jeans. There are lots of great ones out there, but I think you can't go wrong with cowboy boots or a pair of Fryes.

I live in a cool, mild climate, so I usually wear something over my legs, and I find leggings with a pair of cozy socks to be more comfortable than wearing tights, which sometimes pull on my toes, unless I'm going for a particular pattern/texture. No one knows it's not a tight because the sock is hidden in my boot. I have some great plain cotton leggings that I got at Target a number of years ago; find ones that you don't have to think about, they fit so nicely.

Since you are wanting something easy and comfortable, equivalent to jeans, I would advise you to make sure the dresses and skirts you are getting truly ARE comfortable (no spots that are a wee bit too tight, or rub a little) and do not require other, less comfortable or more complicated garments in order to wear them. Does it need a slip? Will your underwear line show unless you wear a thong? It's good to have a nice slip, and some people don't mind wearing thongs, but those are some things to consider. Also, when you're trying things on, remember to move around in the dressing room: sit, squat, bend over, lift up your arms... make sure the dress/skirt is still comfortable doing all those things, and doesn't flash your undies when you bend over! Sorry if this is overly basic, but I feel like it's stuff I only learned over time.

Also, it's great to have cardigan sweaters to wear with your dresses.
posted by sumiami at 7:17 PM on March 23, 2013

I am very slowly but successfully making this transition myself, and I'm finding that jersey skirts and dresses are flattering, comfortable, and manage to look polished but still not-dressy. I've also been surprised to discover that prints, which I was pretty sure I was allergic to for most of my life, work really well as dresses. (That's from a plus-sized shop, but you get the idea. And actually, you might want to browse around for inspiration anyway--the models on all the plus-sized sites I shop with seem to have figured out this causal dress and skirt thing!)

I would love to wear boots with my dresses but I have gloriously thick calves that even wide-calf boots cannot contain. So I mostly wear sandal-esque things. I have two pairs of Dansko Sams, one on black and one in brown, and they work with nearly every dress or skirt I have.

A friend of mine is an all-skirts-all-the-time person and she wears black khaki skirts with her geeky/arty printed t-shirts and it looks great on her.

And I keep my legs bare, even though they're blindingly pale, because I am happiest and most comfortable that way. It seems to be socially acceptable.
posted by rhiannonstone at 11:13 PM on March 23, 2013

Best answer: If you're looking for tights, it's perfect timing at Target -- I just picked up several colors on clearance for $1.50 each. Looks like they're closing out the full-foot models for the season, and bringing in the footless varieties.

I'm working on transitioning from an all-jeans lifestyle too. (And my coworkers are still making endless comments every time I wear a skirt. Hopefully that, too, shall pass.) For a more casual look, definitely boots, and definitely flats. With or without tights. (If it's a day off, I'll wear bike shorts underneath. If it's a work day in my freezing cold office, it's tights.)

And as a person with 14 inches difference between waist and hip, I'm 100% a fan of dresses over skirts. Skirts always ride up on me, which is probably why I avoided them for so long. But dresses, for the most part, stay where they're meant to be. And you can still throw a cardigan or sweater over the top for a top-with-skirt look.
posted by themissy at 7:42 AM on March 24, 2013

Wolford. The. Best. Tights. Ever.

They last forever (years), and are soft and comfortable. Worth the eye-popping price not to have to worry about them ever again. Except to get new colors!
posted by nanook at 6:15 PM on March 24, 2013

I never wear flesh-coloured tights because they are always too dark for me and look like I have fake-tanned only my legs. If it's cold, I like leggings or tights - leggings if the dress is a little short when I sit down in particular as they offer a bit more coverage. I only wear opaques, though, and very occasionally fine fishnets.

I tend to wear mine with a pair of brown boots which would probably be described as 'riding boots', or if I'm being less dressy, some coloured flat boots. In the summer I like Birkenstocks or ballet flats.
posted by mippy at 10:33 AM on March 26, 2013

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