A Thorough Lesson on How to Look Chic While Staying Warm

When my mom took me home from the hospital after I was born on a blustery December evening, she dressed me in a little white snowsuit covered in tiny pink hearts. I obviously can’t remember how I felt about this outfit at the time, but based on my mom’s description of it ("adorable!"), it’s highly plausible that this was the last time I looked chic in cold weather.

Since becoming sentient enough to start thinking about style in the 30 years that have transpired, I’ve always felt incapable of dressing in the cold beyond the basic accomplishment of protecting myself against frostbite. The challenge of factoring in this glaring practical imperative always takes precedence over any expression of personal style because it possesses the ultimate trump card, which is physical comfort! I haven’t figured out how to find a happy medium yet, so that’s why—more often than not—I end up wearing jeans and a random big sweater with sneakers. Not a bad outfit, per se, but also not a particularly thoughtful one. And the thing is, I know that the happy medium of an equally stylish and functional cold-weather outfit exists because I see other people wearing them. That’s part of what frustrates me. Somehow when I make my attempt, the layers don’t lay right, the shoes are all wrong, or I’m not warm enough and I vow never to leave my apartment without my black floor-length puffer coat ever again (even though I kind of hate how it looks every time I wear it).

This year, though, I’ve decided to lay the groundwork early and—having fully accepted that dressing stylishly in the cold doesn’t come naturally to me—actually learn how to do it in a regimented way. I launched my curriculum in one of our nation’s most lauded destinations for higher education: an iMessage group chat. I texted my friends Amelia Diamond and Haley Nahman because of a photo I have favorited on my phone from the last time we were all together when they happen to be wearing two of the most perfect cold-weather outfits I’ve ever seen. Amelia is wearing bootcut jeans, a thick ivory cable-knit sweater, a short houndstooth puffer coat, a chunky ribbed beanie, Fair Isle–knit mittens, and Blundstones. Haley is wearing cream denim utility pants with taupe patches, an orange scarf and hat, brown suede mittens, and a light brown puffer coat with a bright orange lining and a red bandana peeking out from one of the pockets. Not only do they both look incredible, but they also both felt warm and content on what was decidedly a very cold day without trying too hard. The precise combination I’m seeking to cultivate.

"For me, the beauty of dressing in the cold is the opportunity to wear multiple things at once,” Haley ruminated. “In the summer, when the weather only permits me to wear a couple of things, I feel like I'm trying to paint a portrait with only one or two colors. Those two colors need to be extremely special and dialed in if I want to express something specific. If my style were more based around statement pieces (like I think yours is), those conditions are pretty much ideal: Your one or two special items are front and center, unencumbered by layers."

Um, hello, is she a doctor? My illness is finally diagnosed! She was absolutely right: I’m a statement piece girl and never feel quite like myself when I’m wearing layering-friendly basics. This insight was an extremely helpful starting point for trying to figure out a way into late-fall and winter styles that feel like "me".

Haley also shared a few bits of shopping advice that I really appreciated:

• "One of the fastest ways to bring in novelty in the winter is via different colored hats, scarves, and socks—especially because they're cheaper than other winter garments and thus easier to collect."
• "I'm partial to a shorter coat in the winter because it doesn’t cover everything up in one fell swoop. My most-worn outer layer the past few years has been a cropped reversible puffer: bright orange on one side, light brown on the other."

Amelia chimed in with her two cents as well. While her confession that she can’t stand her neck being exposed when it’s cold (even indoors) because she thinks it looks like “the belly of a dead worm” was the greatest gift I could have possibly received, I also loved her tactical, no-fuss cold-weather shopping advice:

• "When it’s really cold, I almost always layer one of those super-lightweight packable/stuffable puffers (Patagonia or Uniqlo) over my outfit or under whatever coat I’m wearing, because you don’t really see them, they don’t add bulk, they usually stretch over whatever I’m wearing, and they add a layer of insulation."
• "I find the best 100% merino wool sweaters on eBay. I collect them! I have fun searching for them. (some searches: 'vintage Dale of Norway', 'vintage Aran sweaters' … they don’t actually have to be 'vintage', but it pulls up good results; also I tend to like the men’s selection best). I don’t mind holes—they can look cool, but they’re also easy to get repaired."

My goal is to try not to buy too much additional stuff as a part of this experiment since I already have plenty of clothing, but I took note of these specific recommendations because 1) I thought they were interesting and might be helpful to others who feel similarly challenged and 2) they shed light on both the limitations and capabilities of my existing wardrobe. For example, I have a solid collection of colorful socks that have always been one of my most fruitful resources for spicing up cold-weather outfits, so I was pleased to hear I was on the right track where those were concerned. I also have one of those ultra-thin puffers from Uniqlo that I often pack in my suitcase if I’m traveling somewhere cold since they can be compressed to almost nothing, so the reminder that this was another great existing tool in my toolbox—whether I’m traveling or not—was a good one.

That said, I am enchanted by the idea of acquiring a short puffer or a reversible coat, especially after hearing Haley’s articulation of the logic of their appeal, so I started doing a bit of Googling to see what was out there in the secondhand space. Here are some that caught my eye:

Invigorated and inspired by my group chat conversation, I commenced part two of my lesson plan and reached out to two professional stylists, Dione Davis and Caitlin Burke. I'm a longtime admirer of each of their styles, in general, but especially when it comes to layering. They both have a uniquely compelling approach to connecting the dots of various wardrobe items into a fluid ensemble that’s both wearable and interesting at the same time. Given that, I was curious if they could suggest cold-weather outfit "templates" I could use as a jumping-off point.

Caitlin, who actually thinks it’s easier to get dressed in the winter than in warmer seasons (I’m in awe), shared that her favorite template is "wide-leg trousers, a fitted tee, and an oversize blazer." She also mentioned one of her go-to cold weather accessories is "a blanket-size, oversize scarf that can be wrapped into a chic balaclava (there are plenty of how-tos on TikTok!) or draped over your coat to create a dramatic cape-like effect."

Intending to combine these two pearls of wisdom, I turned to my closet and pulled out an oversize vintage blazer, Autumn Adeigbo trousers, and Iris & Ink heeled boots. I don’t have an oversize scarf, but I do have an actual blanket that seemed like it would function just as well, so I looked up a balaclava tutorial on TikTok per Caitlin’s suggestion and gave it a try (it was shockingly easy—not to mention fun). I also tried the cape version, which felt extremely elegant. Consider me a newly minted fan of wearing blankets as scarves and of this outfit template in general.

Dione generously shared one of her standby templates as well: “Nothing inspires me more than when I find the perfect dress-over-pants combo that’s already in my closet. Preferably a knit dress over wool wide-leg pants styled with tall boots for additional warmth and a thick, long pair of Woolrich socks underneath.”

I don't have a knit dress, but I do have a long cardigan from K.ngsley that I thought could work as an alternative. I belted it to give it more shape and paired it with a matching beanie, wide-leg pants from Modern Citizen, and vintage boots. I tried adding a long black coat, but it didn't quite work. It felt a little severe and proportionally too long. "I think a lot of people who generally struggle with their winter wardrobe have put all their stock in the wrong coat," Dione says (it wasn't lost on me that this advice was becoming somewhat thematic during my mission). Like Haley, she recommended a shorter silhouette to add balance, which I didn't have, so I swapped out the coat for a red crew neck sweater worn as a scarf that I thought worked much better. I liked this outfit a lot, and I think it would really sing with the right coat. Still, when tricking out either of these outfits for seriously cold weather, the right coat is only as good as what you've layered underneath, which is probably why both Dione and Caitlin recommended stocking up on Heattech from Uniqlo. "Don't wait until it's already cold outside," Dione emphasized. Roger that! I currently own zero warm underlayers, so I think this long sleeve T-shirt and this pair of leggings would be practical investments. 

The third and final phase of my self-imposed curriculum is simply practicing what I've learned for the next few months until it starts to get legitimately cold in New York. Hopefully, by then, it will feel more like second nature so that I won't have to think so damn much about it when I'm getting dressed. I plan to continue experimenting with the outfit templates that Dione and Caitlin recommended, re-creating them with different items and maybe even documenting the ones I like best with my phone, so I can always reference them in a pinch. I'm also going to keep up my quest for the perfect short winter coat since that feels like the biggest hole in my existing wardrobe. And other than that? I guess just enjoying my new degree in sub-zero fashion preparedness.