How do I be cute in the winter?

January 24, 2016 6:13 PM

I am a lady who has recently gotten into dressing more feminine. But I am also a lady who has just moved to the Midwest, and it is winter here now. How should I be dressing?

Due to a combination of buying and enjoying a whole bunch of fun, summery dresses this past year, and the dawning realization that as I age I am becoming more and more pear-shaped and therefore more difficult to fit in trousers, I've become really into the idea of dressing more femme, especially in my professional life (I am a college professor with an institutional code of business casual). The issues are . . . well, there are a few.

1) My work "outfit" has been dress pants of varying bland colors, tank tops of varying bright colors, and cardigans and blazers, for over a decade now. I like the simplicity of being able to mix and match almost all of my clothes with each other, but I am bored and feel more blah than business casual these days. 2) Pants. It's getting harder and harder for me to find trousers. I have always had long legs (I'm 5'11"), but the recent expansion of my butt and thighs make it impossible to find pants that fit. I'm pretty curvy now, whereas before I was just tall. 3) I absolutely love the fun sundressy things I bought this past summer, which were a step out of the box for me and I enjoyed wearing them greatly. But I can't wear any of them now that it is in the 20s regularly.


What should I be buying that will give me the same feminine feeling of those summer dresses and yet won't cause me to get frostbite? And how do I integrate those things into a cohesive wardrobe? I will say that the other day I went to work wearing a long-sleeved jersey knit tunic with skinny jeans, black boots, and an infinity scarf AND I FELT SO COOL AND AWESOME but that was an outfit I conceived of all together and had to purchase each piece of the week before wearing, and now I am not sure how else I can wear those items (except the boots I guess).

posted by chainsofreedom to Clothing, Beauty, & Fashion (13 answers total)

Well, MORE tunics and skinny jeans and scarves, then you can mix and match! Also, long sleeved dresses and fleece lined leggings with boots and scarves (that's my look in winter, for similar curvy reasons). Ponte knit dresses are pretty thick and can be flattering. I get mine at Boden, Land's End, Ann Taylor, wherever really. I also get cute dresses and scarves at Target.
posted by leesh at 6:16 PM on January 24, 2016 [2 favorites]

Pinterest is wonderful for this kind of shopping situation!
posted by Hermione Granger at 6:23 PM on January 24, 2016

I went to work wearing a long-sleeved jersey knit tunic with skinny jeans, black boots, and an infinity scarf AND I FELT SO COOL AND AWESOME

Naturalized Midwesterner here. This is how I dress all the time in the winter. Don't be afraid of the close-fitting knit pants you'll find everywhere that are kind of like leggings--I wear those with tights and tops that come down to at least mid-thigh. (I buy leggings cheap at places like Meijer and Target.)

Otherwise, long (mid-calf) skirts in heavy knit fabrics with tailored blouses and open cardigans with some drape. Layer with opaque tights (or even long underwear) underneath, again with knee-high boots.

A-line skirts were made for women with curves. And if you layer properly underneath, a skirt can actually feel warmer than long pants.
posted by tully_monster at 6:29 PM on January 24, 2016

Wisconsin girl here. Boots and scarves are the main accessories for winter, followed by knit or fur hats. Look for dresses with lining, because boots and tights require a lined dress (or a slip), to wear comfortably and without fear of the dress riding up. The bonus is you can wear the boots with skirts and summer dresses too.
I like J Crew, Lands End and Fair Indigo for knit dresses although since I'm very cheap I only buy secondhand. Have fun!
posted by areaperson at 6:45 PM on January 24, 2016 [1 favorite]

I am currently enamoured with flaxseed linen and cotton dresses that hit me just below the knee. Worn with boots, tights, and colorful socks that show just above the boots and colorful full scarves. There are several flax brand retailers on line, and buykud Is my current favorite for heavier cotton.
posted by raisingsand at 6:58 PM on January 24, 2016 [2 favorites]

I recently got myself a job where I need to dress professionally - not skirt suit & pantyhose but just your typical polished and put-together office wear. I haven't worked out of the home in over a decade and corporate wear is NOT my style at all. I carry my weight in my stomach so almost all pants that are not stretch jeans are a no-go for me.

So my uniform for the winter turned out to be putting a dress over leggings with boots (any height from knee-high to calf-height to ankle boots, some with chunky heels and some flat). Most of my dresses are sleeveless or short-sleeved (summer dresses!) and nothing much longer than my knees - I have a bunch of toppers to layer over them (I like different lengths of cardigans that are meant to be worn open - they don't have fasteners at all) and scarves to cover lower/more open necklines.

This uniform is great in the winter (leggings are warmer than tights for sure), comfortable, and versatile (since all the layers mix-and-match across outfits and seasons). I look for dresses that are made of heavy synthetic fabrics that don't cling, with high waists at the ribcage, either with flattering draping or ruching, or fit-and-flare.

I often tend to an all-over print dress with plain leggings but I also like doing a solid-color dress with those trendy printed leggings. I feel like there's lots of options to explore with this uniform and while it's more feminine than I have dressed in the past, it's comfortable, modest, and practical. I find I am enjoying wearing dresses more than I used to, for sure.
posted by flex at 7:11 PM on January 24, 2016 [2 favorites]

I'm really digging velvet leggings as an alternate to skinny jeans with your tunics this year. I either buy the K.Bell velvet (really velour) leggings off EBay, or for fancy person dollars, the high waisted Daria pant from Aritzia (which you can get in real velvet) is super slimming and ultra comfy.*

*the wide waist panel would be so good on bigger bodies but of course they don't venture anywhere NEAR plus sizing, ugh. consult the measurements - I sized up for a comfy waist & will need to hem the bottoms.
posted by Juliet Banana at 9:21 PM on January 24, 2016 [3 favorites]

Sweater tights, sweater tights, sweater tights. If they don't exist where you live, try the internet. I've never seen truly great ones in the US, but Japanese ones are available all over online. Look for at least 180-200 "denier" (whatever that is, it seems to indicate thickness) or more. My favorite pair are normal-looking on the outside, but seem to have space-defying fleece lining (doesn't look thick) on the inside and are 220 "denier." note, if you're buying Japanese, you'll want the biggest size available (often "L-LL" or XL) for comfort's sake.

I used to wear boring pants all winter too (and am also pear shaped) but thanks to winter tights, I haven't worn pants almost at all this whole winter, even on the very cold days! I just combine winter tights with tall boots and a longer skirt (my uniform is a button down, black jacket, black skirt) and change my shoes to something more indoorsy when I get to work.

Good winter tights are the key to unlocking year-round skirt and dress magic.
posted by gloriouslyincandescent at 9:56 PM on January 24, 2016 [2 favorites]

I don't wear trousers, so I had to adapt my style to Scottish & Scandinavian winters.

+ Layers are great. Woolly/warm tights with lined leggings on top (I can remove leggings if my work environment is warm).
+ Smart mid-calf boots OR smart ankle boots. This will depend upon transport, for me.
+ Long-sleeved tees - generally just in neutral colours.
+ Dresses in wintery colours - I like going navy & burgundy in winter. They're similar dresses to what I wear in summer but the colours are just darker.
+ Cardigans (or jackets) to put on top of your dresses, so the long-sleeved tees don't show & you have extra warm.
+ warm cowls/scarves in matching colours to put around your neck. I like adding a brooch which adds a bit of sophistication.
+ ADDED TRICK: Underneath my wintery dresses I occasionally wear a knitted skirt for extra warmth. If you get a thin knitted pencil skirt, it won't show up but you'll have extra warmth in your bum/thigh area.

To make all this look business casual enough, think about colours: dark, matching colours will look smarter than loud, bright colours. Knitted wrap dresses were also my go-to when I worked in an office.
posted by kariebookish at 3:57 AM on January 25, 2016

A specific winter layerpiece recommendation: Uniqlo Heattech. I live in Chicago and I am literally wearing two pieces of Heattech right now (tights and long-sleeve shirt). The "Extra Warm" leggings are really stretchy, so I'd probably start with those. I also regularly layer my beloved collection of short-sleeved dresses/tanks with heavyweight cardigans, scarves, and shawls, so maybe give that a try!
posted by torridly at 9:40 AM on January 25, 2016 [2 favorites]

Fleece-lined leggings are a DREAM. Get them in black and they look like tights or regular leggings, but they're really insulating. I wear them with dresses and a slip underneath for added warmth and to keep the dresses from clinging to my legs.

I'm cheap and buy mine at Bed, Bath & Beyond for $10/pair, which was a weird discovery while wandering the aisles, but they last me about a year before they start pilling from washing and wearing.
posted by E3 at 12:52 PM on January 25, 2016

to get the most out your tops, i suggest a little used clothes shopping for skirts. Lately i've been wearing long full skirts. they don't seem to be in style right now, so that is why i suggest used.
posted by Gor-ella at 1:11 PM on January 25, 2016

I adapt a few of my warm-weather dresses to Midwest winter, actually, through the use of large cardigans and fleece tights. This obviously doesn't apply to, like, actual gauzy cotton sundresses, but lightweight knits and shirt-dresses adapt well. (Think things you might normally wear on a warm fall day, rather than a summer one.)

For example, this, this, and this have all made it into my winter wardrobe, just layered up.

For guidance on the layering I like the (sadly defunct) blog What Would A Nerd Wear--she has several items she wears year-round. Plus, it's nice to see an ordinary person pulling off some more daring combos--there's a lot of stuff I wear now that I never would have thought could work, until I saw it on the blog.
posted by We put our faith in Blast Hardcheese at 4:08 PM on January 25, 2016