How do I wear dresses?
September 19, 2022 4:16 AM   Subscribe

I've been wearing a uniform of skinny jeans, tee, sweater/cardigan, and black boots for decades. I'm ready for a change and could use advice!

I like my uniform, but lately I've been wanting to wear dresses more. What's stopping me is that 1) they seem expensive! Can I wear the same dress multiple times a week like I do with jeans? 2) I like to be warm in the winter, and 3) I walk a lot so need comfortable, solid shoes.

Can you give me some advice like I'm 5 and I've never bought clothes before? What kind of dress + shoes would you buy to look great that can do a few miles of outdoor commuting a day? I don't have a strong personal style - like good cuts and happy with color.

I'm 40s, tall, small chest and waist, wider hips. Size 12-14 US.
posted by jebs to Clothing, Beauty, & Fashion (35 answers total) 8 users marked this as a favorite
Of course you can wear dresses multiple times per week. But you have to remember that while jeans are typically separated from your skin by undies, a dress tends to have a bodice and sleeves that are frequently intended to be worn right next to the skin. So your sweat/skin oils get absorbed into the dress, limiting your ability to wear it for days on end. Of course you can pick styles that can be layered with a shirt/blouse/t-shirt. In that case, you probably don't want the dress to be made of thin jersey type material but something with a bit more weight so it looks nice with a layer underneath. There are also dress shields. A skirt and separate top could give you a similar silhouette and remove the problem.

To create a uniform, pick dresses in neutral colour or black and add interest with different scarves cardigans, jackets, belts etc. If you're going to wear a dress multiple days you do not want people to remember the bold pattern or unique want the dress to provide a background silhouette so that people can notice the changing scarves or jackets, not the dress.

It depends on your waist/hip ratio. If the curve is pronounced, you may want to explore wrap dresses or any skirt shape that gets looser from the waist down. If the curve is not very pronounced styles where the skirt is a bit more fitted would also work nicely.

Winter commuting and robust footwear - traditionally, that problem has been overcome by a nice long coat and boots. For boots that look too bulky indoors, many people keep a pair of shoes at work to change into. This seems to be especially popular for areas where it gets both cold and wet. If your jeans have been hiding your boots to date, consider that as an option.
posted by koahiatamadl at 4:51 AM on September 19, 2022 [8 favorites]

For dress styles, I recommend searching "fit and flare" and see if that style feels flattering. With a smaller chest and wider hips I think this is a great style.

Jersey/knit types of fabric have some stretch to them and should be comfortable and machine washable. I would think about getting a few of these and wearing each for just one day at a time. For special occasions, something a bit more structured at the top. I think your current uniform lets you get away with repeat wearing in a way that dresses won't, because dresses look different enough from one another that it's more noticeable if you wear the same one multiple days in a row, where with jeans, no one knows if it's the same pair, and they are thick and rugged enough that it takes a while for them to lose shape and they never wrinkle. Choosing non-wrinkly dresses in dark colors may get you some flexibility there.

You can also pair a dress with leggings and boots (play around with boot styles to see what you like), especially all fall and winter.
posted by happy_cat at 5:06 AM on September 19, 2022 [1 favorite]

1) I think in most places, yeah, you can wear the same dress multiple times in a week although it's probably best if a) it's a more understated dress - no really obvious pattern, e.g. and b) you accessorize it a little differently each day - different color tights, cardigan, blazer, scarf, whatever. Oh and koahiatamadl is right about sweat/grease - I wear undershirts under pretty much everything, but dresses tend to get dirty/require laundering on a schedule more like for a shirt than for pants.

2) Warmth: tights or leggings under the dress. I like footless tights/leggings for walking because then I'm not wearing out the foot part way ahead of the leg part.

3) Personally I wear the same shoes with dresses as I do with jeans/pants. Big shoes can look clunkier with bare/tights-ed legs than they do with jeans, but not necessarily in a bad way. Proper athletic shoes look a little sillier with a dress/tights than they do with jeans.

I won't recommend specific dresses because I'm the opposite shape to you!
posted by mskyle at 5:06 AM on September 19, 2022 [3 favorites]

In the cooler seasons i wear dresses over skinny jeans, or leggings, these are dresses in lenght from mid-thigh to just below the knee, because i do like shorter dresses but hate showing my knees and legs.
posted by 15L06 at 5:17 AM on September 19, 2022 [2 favorites]

I like to shop secondhand. People buy dresses and never wear them so dresses are often resold online or donated to thrift stores without ever being worn. You can get beautiful dresses for super cheap this way. Also the cost of a new dress can be offset by the fact that it is a whole outfit. Example: you buy a long sleeved maxi dress instead of a blouse and a jacket and a pair of pants.

Warmth is all about choosing the warmest cuts and fabrics. Layer up with tights, cardigan, scarf.

Shoes are a matter of personal taste. Fashionable people are wearing a lot of practical shoes with dresses. Here are some examples. I wear sneakers and boots with dresses all the time.

As far as choosing a particular dress, I would try on a lot of different styles. Dresses often look really different on different bodies. Some of my most flattering dresses lack "hanger appeal".
posted by RobinofFrocksley at 5:24 AM on September 19, 2022 [6 favorites]

I'm going to suggest something a little different. You should buy this exact dress in a solid color. I bought one after I saw a link to it here on metafilter, and then I liked it so much I bought a second one.

Things that are good about this dress:
- it's a flattering cut on a wide variety of body shapes
- it's inexpensive
- it's very plain and so can fit with a bunch of different styling choices
- it's comfy enough it can be a casual wear on the couch on the weekends dress if you decide you're not a dress person

So anyway I'd recommend you buy this dress first, and give dresses a try through it. Check out the Amazon reviews with pictures to see how some other folks are wearing it (belts, scarves, sweaters, big chunky sandals, dainty little flats) and try what suits you most from things you already have. It'll give you a chance to learn what you like about dresses and if you like dresses at all without a big investment.
posted by phunniemee at 6:12 AM on September 19, 2022 [6 favorites]

- it has pockets
posted by phunniemee at 6:12 AM on September 19, 2022 [7 favorites]

If you like your current boots, why not wear them with the dresses? I wear opaque black tights and black boots most of the time when I wear dresses. I like merino wool dresses in the winter (one random example of something basic). Thredup is a good site to find secondhand dresses once you find some that you like.
posted by pinochiette at 6:14 AM on September 19, 2022 [9 favorites]

You may also find skirts and tops give you more flexibility.
posted by The Underpants Monster at 6:38 AM on September 19, 2022 [2 favorites]

For ease of laundering, get a few full slips to wear under a dress. You can have a new slip on a day you’re re-wearing a dress.
posted by Hypatia at 6:43 AM on September 19, 2022 [4 favorites]

Dress shields are another useful way to get a few wears out of a dress between washings.
posted by corey flood at 7:03 AM on September 19, 2022 [1 favorite]

Can I wear the same dress multiple times a week like I do with jeans?

The answer to this is it depends. Outside of work, you can wear the same dress a few times a week. In some offices, those with a strong emphasis on dressing professionally, you really can't wear the same dress more than once a week. In others, it would be OK to wear the same dress twice if you accessorize it differently. It would also depend on the dress. Wearing a dress with a bold pattern or a unique cut a few times a week will be more noticeable than wearing something more plain. This is an instance where it's probably better to pay attention to what other people around you are doing. (Since you said US sizes, I'm assuming you are in the US. Europeans I've known have been much more relaxed about wearing the same dress on multiple days.)

(Before someone jumps on me for using "can't" - of course no one is going to stop you - I'm talking about what is considered socially acceptable, and as I said, that will vary.)

I would strongly suggest only buying dresses with pockets, especially if you're used to wearing pants. Also, I'd start with one dress so you can figure out what works for you. I've discovered, for instance, that I'm really uncomfortable with anything that isn't at least a few inches below my knees. But I only learned that by going through the day with a dress that was knee length.

Good luck. I love skirts and dresses, and I find them way more comfortable than pants.
posted by FencingGal at 7:30 AM on September 19, 2022 [5 favorites]

There was a challenge to wear the same dress for 100 days; some of the articles at the google link might be useful. Most seem to stress choosing the right dress (light wool, dark solid color, plain cut) and accessories (scarves, jewelry, cardigans) and tips to make the dress look like a skirt.
posted by beaning at 7:44 AM on September 19, 2022 [5 favorites]

What kind of dress + shoes would you buy to look great that can do a few miles of outdoor commuting a day?

The pandemic has spared me my summer "involuntary femme" phase of skirts and the occasional dress at work for three years now, but before that in warm weather I usually wore ballet flats. This wouldn't work in a very formal office but is fine for business casual, especially if you avoid any frilly adornments.
posted by praemunire at 7:46 AM on September 19, 2022 [2 favorites]

One of my favorite dresses for the office was a lightly-tailored denim shirt dress with an A-line shape and princess seams. I'm having trouble finding an exact match online, but it was similar to this one, but with short sleeves, and mid-calf length instead of midi (although, to be fair, a lot of so-called midi skirts hit me at mid-calf.) It was hard-wearing, which was great for my half-bus, half-walking commute, and it was plain enough to take a lot of different kinds of accessories - dress casual shoes or boots, sweaters, scarves, jackets, etc. Something like that could be a good transition from your customary jeans.
posted by The Underpants Monster at 8:30 AM on September 19, 2022 [1 favorite]

I'm almost 40, tall, small waist, wider hips. Size 8-12 US (I think).

My One True Skirt is easy to make. Cut a really big circle in a large piece of fabric of your choice. Or two half-circles and sew 'em together if your fabric isn't wide enough (add pockets to seam if you're a side-pockets person). Cut a hole in the center for your waist. Hem the outer edge. Turn the inner edge into a drawstring (easy) or add a zipper (harder). Remember to account for seam allowances (meaning that it gets smaller after you hem it).

I use wool, which can be worn for several days. I wear several different One True Skirts, which can be rotated.

If you wear pants under it and are careful about pockets, the One True Skirt can be used as a temporary tote bag to haul loads around. Great for gardening or carrying groceries out of the store without a bag. Also collects compliments.
posted by aniola at 8:35 AM on September 19, 2022 [1 favorite]

Nthing suggestions to get some slips! I've generally found them to be a lot more prevalent/affordable at thrift stores.

Also, it sounds like your uniform could translate nicely to a dress-wearing lifestyle, if your boots look cute with dresses! T-shirt dresses like these ones might work, and they're not so formal that you'll feel like you're donning a gown to go to work. As long as you're wearing tights or leggings, it should be comparably warm to your skinny jeans outfit.
posted by quatsch at 8:47 AM on September 19, 2022 [2 favorites]

There was also an AskAManager where someone got in trouble at work for doing the 100-day dress challenge.

And AAM and the respondents all agree the discussion never should have arisen given the only issue was the dress itself being reworn - not odor, stains, or any other job-related appearance concern. I don't know the subsequent comparisons to having/rotating multiple items of the same "perfect" piece completely apply as, to me, wearing the same item repeatedly means having to be even more aware of cleanliness and wear issues that need addressed.

So, keeping the cleanliness caveat in mind, I would think there should be no problem if the plan is to rotate days of the dress with days of not-the-dress.
posted by beaning at 9:17 AM on September 19, 2022 [1 favorite]

RE winter, fleece-lined tights are awesome.
posted by metasarah at 9:29 AM on September 19, 2022 [5 favorites]

Fleece and/or wool tights/ leggings are additional options as the mercury drops.

For really cold commutes you may want to put on pants (e.g. sweat, rain, snow etc.) over leggings/tights or wear a longer coat.

I would also put in a plug for finding ankle boots where it is (fashionably) feasible to discretely wear socks.
posted by oceano at 9:38 AM on September 19, 2022 [2 favorites]

It sounds like your a similar shape and size to me. I love that style dress from Amazon and wear fit/flare almost exclusively. In the summer I go bare legged and I wear flats. In the winter, I put a pair of coordinating solid leggings under it and wear knee high boots. In the fall/spring when I still need a little warmth, I use tights and boots or tights and flats or loafers.
posted by kathrynm at 9:54 AM on September 19, 2022 [1 favorite]

As a tall lady frustrated with tights that don't stay up, I switched to these men's seamed dance tights in black, and never looked back. They're fitted to the leg instead of being just stretchy and tube-shaped, and the waist actually goes all the way up to my waist. They're truly opaque, and warm enough for outdoors without being too hot for a heated office. They cost a bit more than department-store ladies' tights, but one pair has lasted over a decade of regular wear without a single snag.
posted by The Underpants Monster at 10:33 AM on September 19, 2022 [3 favorites]

If you want to keep to your current laundering schedule, you could just get a flattering wool skirt and wear it with exactly what you already wear with jeans. If you like the silhouette you can get a few dresses and see how that goes.
posted by ananci at 10:43 AM on September 19, 2022 [2 favorites]

On shoes with dresses, I wear dresses basically like that Amazon dress to work all year. In the summer with flat sandals I can walk in, in the winter with tights and flat ankle boots I can walk in. Works great.
posted by LizardBreath at 10:46 AM on September 19, 2022 [1 favorite]

I would say to NOT rewear a dress multiple times a week unless you are doing the "I wear the same uniform black dress every day" sort of thing. If the outfit is remotely distinctive, I notice. I go two weeks between rewearing an outfit, but I note my outfits are distinctive. Jeans are same old old same old most of the time, so that's why nobody notices if you rewear them. However, I did buy dresses of same style/different color and wore one right after the other and nobody noticed that.
posted by jenfullmoon at 11:20 AM on September 19, 2022 [2 favorites]

Response by poster: Thank you all so much!!
Every answer is so helpful, I really appreciate it.

Useful to know the term fit and flare, and that fleece tights exist. I'm hoping the flat black ankle boots I already have might work, but I think I need to see it all on first. In my mind they'll be too clunky, but we'll see.

To be honest I hadn't even thought about skirts, and I'm intrigued by the plain black wool skirt uniform idea too!
How exciting :):):)
posted by jebs at 11:36 AM on September 19, 2022

I bike commute and wear dresses a lot all year round, and I wear this stuff on my bike, including in the rainy winter, so you can definitely find dress/shoe options that will work.

I'm going to guess that the boots you've been wearing with your skinny jeans will work great with a lot of dresses, or get whatever kind of boot feels comfortable. One trend right now is shorter boots with dresses (I see younger folks wearing Doc Maarten style boots with skirts and dresses, and I've been wearing a pair of oxford low boots this way too lately). You can definitely rock that look if you like it, and add leggings and socks or tights for colder days (fleece tights and leggings are great when it's really cold). A more traditional way to pair boots with dresses is to wear knee-high boots with a longer, mid-calf dress. You can wear socks when it's not too cold (knee high for under the boots is more comfortable with tall boots) or tights or leggings/socks again. You don't have to wear a heel or fancy shoes with a dress or skirt.

As folks have said, the issue with wearing a dress multiple days might be stains and odor, especially in your armpits. I'm going to try the dress shields folks are talking about because often the only reason a dress feels dirty to me is some armpit odor. But, I also prefer dresses with a short sleeve or long sleeve rather than sleeveless because otherwise whatever I wear on the outside (like a cardigan) then gets the odor.

As for wearing the same one multiple times in a week: absolutely you can do this. You might experiment with a simpler style and color dress (like black, gray, dark green, or navy) and add color with cardigans. Like one day a bright pink cardigan over a navy dress would be a different look than a jean jacket, or a pullover vneck. Also try a few different styles (like a shirt dress, wrap dress, and fit and flare dress). But, if you get a dress in a bright color, you can wear it one day by itself and another day with a pullover sweater, and that can work like two separate outfits too.

Cotton is great. Wool is great too but gets a bit pricier. Synthetics tend to show wear sooner. You might try buying a few cotton dresses from someplace less expensive like Loft or Target or Lands End on sale, that sort of thing, and see how they work for you.

You might find you want a shorter cardigan for your dresses. Even before the new shorter/cropped style came into trend lately, I know I would generally prefer a shorter cardigan to wear with dresses and skirts because the waist can be a bit higher in a dress.

I'm not on TikTok much, but I know on TikTok and Instagram reels there are all sorts of "teacher outfits" that fashion content folks are creating right now, and that's the short of thing you might find aimed at folks your (our) age. You might get some ideas there.
posted by bluedaisy at 11:41 AM on September 19, 2022 [3 favorites]

I'm hoping the flat black ankle boots I already have might work, but I think I need to see it all on first. In my mind they'll be too clunky, but we'll see.
Ha, I was writing about this before I saw your reply. I bet they'll look great, but I also know it can take our eyes awhile to adjust to new styling. Fashion sneakers with dresses are super popular right now, and I've been experimenting a bit with that myself.
posted by bluedaisy at 11:43 AM on September 19, 2022 [2 favorites]

Oh! And one more thing! I ALWAYS regret buying dresses without pockets. There are lots of great dresses with pockets. Yes, there are many cute ones without pockets. But if you're used to wearing jeans, giving up pockets for everyday dresses might be a step too far.
posted by bluedaisy at 11:44 AM on September 19, 2022 [4 favorites]

Apologies if this is duplicate information--haven't been able to read everything.

In addition to fit and flare, I would also recommend searching for "wrap dresses". I'm your size and it sounds like we have similar proportions. The wrap can be faux (just a tie at the waist) or a true wrap, which can be a little more fiddly on a windy day. You can find them in more casual knits and more weighty/formal fabrics and patterns.

If you work in a more formal environment, I also think Calvin Klein and Lands End has some nice basic dresses in sheath silhouette, which reads a little dressier to me. Personally I often have to size up in Calvin Klein.

The price in my mind for a work dress is $50. Less is a deal and to pay more I have to really love it. Choosing plain/simple dresses and pairing them with different sweaters, accessories, etc. would make it easier to re-wear throughout the week (but really I don't think many people notice this).

As far as comfort, I live somewhere hot and swampy so I almost never wear a dress without shorts underneath to prevent thigh chafing (there are lightweight/wicking shorts made specifically for this, or regular bike shorts could work, or you may not have that issue). You might be in a cooler climate in which case tights would serve the same purpose. For shoes, depending again on your environment wearing sneakers with dresses is popular right now. I also have good luck with Anne Klein flats and wedges (I think there are 'sport' and 'i-flex' lines...don't really know what it means). Ankle boots and lug sole shoes are in right now. Personally I think ankle boots are always in, but both can sometimes seem "clunky," but you'd be on trend. :-)
posted by kochenta at 12:57 PM on September 19, 2022 [1 favorite]

As far as comfort, I live somewhere hot and swampy so I almost never wear a dress without shorts underneath to prevent thigh chafing (there are lightweight/wicking shorts made specifically for this, or regular bike shorts could work, or you may not have that issue).

In hot weather I wear men's boxers under skirts. It's very comfy.
posted by The Underpants Monster at 1:09 PM on September 19, 2022 [2 favorites]

I’m another skirted winter bicyclist (Minnesota, so not messing around). I find it much easier to dress warmly with skirts because I can wear warm leggings or “base layers.” Jeans are cold! My cotton fleece leggings in particular are magical — warm when it’s cold but not overly hot in warmer weather. For freedom of movement, I recommend knee length A-line skirts. I don’t mess with dresses for the aforementioned laundry reasons.
posted by Comet Bug at 5:34 PM on September 19, 2022 [1 favorite]

Dresses with pockets are great, but hard to find. And some may have pockets, but only big enough to hold your hands, not your phone (or at least mine may fall out if I sit) or keys. I am a big fan of pocket belts/fanny packs, which there are plenty of on Etsy even if you can't find them as easily IRL. (Blue Moon Katherine is one I patronize a lot.)

I do wear leggings a lot, or straight up buying long skirts and wearing sweatpants under them in winter.
posted by jenfullmoon at 5:45 PM on September 19, 2022 [1 favorite]

I wear dresses as often as I can!

1) Style: "Fit and flare" is a good choice for me, and I find "A line" often works too. I'm going to recommend eShakti - they can make a dress custom to your measurements, AND most of them include pockets (or have that option, at least). Pockets work great in fuller skirts, where the contents are masked by the fullness of the skirt. I haven't ordered from them in a couple of years, but I find I like their jersey knit fabric the best. Your mileage may vary.

2) Shoes: I live in the Pacific Northwest without a car. I'm wearing ankle boots now, and will switch to knee-high when the weather gets colder. Sometimes I wear rubber rain boots.

3) Tights/leggings: wear these in the right thickness for your body and the local climate! I have worn fleece leggings when it gets too chilly for me here, but most of the time I'm happy in some nondescript athletic tights.

4) Re-wearing dresses: Like others have said, you need a dress in a neutral color to pull this off, but it might be easier than you think. You can probably pull pieces from your current wardrobe to style the dress differently to make it less obvious. Throw a sweater/blouse/cardigan/blazer on top. Try a belt. Try scarves!

Have fun! I'm excited for you.
posted by invokeuse at 9:41 PM on September 19, 2022 [1 favorite]

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