My Realistic Winter 2025 Lookbook
Second trimester of pregnancy 🤝 freezing cold temps.
Putting together this season’s Lookbook during my second trimester was a real exercise in patience. I was equal parts annoyed and amused by how often outfits that seemed perfect in my head looked completely different once I put them on. And it definitely didn’t help that winter is when I feel the least inspired by my wardrobe.
Regardless of whether pregnancy is part of the equation, I’m guessing most people can relate to the experience of getting dressed within certain constraints. From living out of a suitcase on a trip, to dealing with unpredictable weather, to adhering to a strict office dress code, there are numerous scenarios that render your go-to outfit formulas obsolete — which, of course, can be just as frustrating to navigate as it is satisfying to solve.
After plenty of trial-and-error, the 15 outfits below are what emerged for me. I’ll be reaping my reward by referencing them on blissful auto-pilot for the rest of winter.
This is my ideal “going to a work meeting but still want to be warm and comfortable” kind of outfit. I love the visual effect of layering an open cardigan over a crewneck sweater, and these two knits are the perfect length and color for doing that. I like to scrunch up the sleeves of the outer cardigan slightly so the underlying crewneck cuffs peek through. These leather pants have an elastic waist that, when folded down, is very bump-friendly. They’ll easily fit me through the remainder of my second trimester.
The Subway jeans from Still Here fit me until 30 weeks during my last pregnancy. They’re a baggy silhouette to begin with, and I have them in a size up from my non-pregnant size. I like the proportional effect of layering a tight-fitting T-shirt underneath a button down when my pants have a relaxed cut, especially at this stage of pregnancy. The bigger my bump gets, the more I tend to gravitate toward fitted components in my outfits. I’ve already worn this exact outfit twice now — once to the movies, and once on a Saturday out to brunch in our neighborhood. The second time around (pictured here), I added the necklaces, which made the whole look feel more considered.
This outfit came together pretty seamlessly because I just riffed on the one above by removing the denim shirt, adding a cardigan and pearls and hair bow, and switching from loafers to heels. It was just right for a dinner plan I had a couple weeks ago where I wanted to look dressed-up, but not too dressed up. I’m excited to reinterpret it across consecutive wears by swapping in a different color T-shirt or cardigan. I think next time I’ll also put charcoal gray socks on with the heels.
I used a home clothes outfit composed of track pants and a white long-sleeve T-shirt as my initial building block here, then added a sweater, a jacket, and loafers to morph it into something I could wear for a variety of outdoor excursions where I want to remain super comfortable but still look somewhat intentional.
The Rio High Waist Straight Pants from LESET are another pregnancy staple for me (note: not made of natural fibers). I’ve owned this black pair for years, and I just bought them secondhand on eBay in gray so now I have them in two colors. I like these pants even better when I’m pregnant than when I’m not pregnant — it’s funny how that happens with certain things. They have a super high waist that stretches easily over a growing bump without losing its shape, and the legs are the perfect width — tight enough to look tailored but loose enough to look like pants instead of leggings. The base of this outfit (striped T-shirt, cardigan, stretchy pants) is comfortable for lounging at home but also looks polished for an outdoor transition with the addition of a coat, beanie, and colorful sneakers.
The striped Kule T-shirt + black cardigan + demure necklace combo as seen above has become a go-to formula for me across multiple different outfits. These pants from SEA have a elasticized waist in the back, so even though they’re high-waisted they still fit me right now, and I’m guessing will continue to for at least another month or two. I’ll be wearing this outfit out to dinner as much as possible in the meantime.
Another pair of SEA pants that still fit comfortably thanks to an elasticized waist. Like the Canadian tuxedo-esque outfit pictured earlier, the combination of a button down and wide-leg pants here benefits from at least one relatively body-conscious element — in this case, the cropped, form-fitting sweater — to keep the proportions balanced and prevent the look from feeling too loose or shapeless.
A recent favorite home clothes outfit turned running-errands-outfit with the addition of velvet slippers.
These vintage overalls are another pregnancy go-to for me. They’re quite oversized and fit me through my whole pregnancy last time. Layering them over this large-collared vintage white blouse and a navy sweater is a reliable template for me in the wintertime whether I’m pregnant or not, so it was an obvious outfit to include in this season’s Lookbook.
I’ve worn this exact outfit many times over the years, pregnant or not. It translates well to the second trimester thanks to the elastic waistband in the pants (SEA for the win yet again!). The blouse will only fit for a couple more months because it’s relatively tailored through the waist, but I can easily replicate the look with a different shirt. I swapped in my navy and white striped Kule top when the blouse was at the dry cleaner earlier this week, and I have a collarless pinstriped button down that would work well in the future, too.
The ultimate “lazy but very warm” outfit template, which came in handy during the multiple weeks of below-freezing temps in January. I’ve been wearing a Uniqlo heattech base layer underneath these sweatpants, but I’m tempted by these wool/silk blend leggings that Trinity shared in my newsletter last week.
A friend of mine recently asked me if the High Sport pants were good for pregnancy (she was pregnant herself at the time and considering buying them). My honest answer was no, because they are very high-waisted in a thick fabric with only minimal stretch. Mine still fit me for now when I fold down the waist band under my bump, but even that won’t be comfortable for much longer — so I’ve been taking advantage while I can. I plan to repurpose the upper portion of this outfit — a cardigan layered over a T-shirt layered over a turtleneck in contrast colors — with different bottoms once these officially retire, but I’m loving this butter yellow / bright red / cobalt blue (c/o the socks) color combination for now.
The aptly-named Long Belt belt from Still Here has an extra-long tongue, so perfect for an expanding waistline. I really like how it looks when the excess length is looped through like this. This outfit works quite well with a simple white sneaker, but I’d like to experiment with different shoe options the next few times I wear it. Maybe a silver ballet flat…
I really like the layered combo of red tee + gray sweater + black silk blazer as seen in the prior look, so here it is again. I’ve worn this same outfit with my yellow Nike sneakers for a slightly more toned-down look, but generally I’m having a lot of fun experimenting with these leopard boots. I don’t consider myself a “shoe person” in that footwear is not something I get as excited to shop for as other stuff, but I tend to appreciate the transformative power of a fun shoe more than usual during pregnancy, given that they are guaranteed to fit, and also given how often I’m repeating outfits.
I put my favorite vintage coat on over the outfit above to go to a work meeting, and it turned into a look worth cataloguing in its own right thanks to the festive hooded scarf and vintage nautilus brooch.
Despite the non-linear process of putting these outfits together, it’s been nice to remind myself that some things about my sense of style remain constant, no matter what variables (in this case, a changing body) are thrown into the mix. The same color combinations I’ve always gravitated toward still click. My signature jewelry pieces will always make an outfit feel more personal to me. Prioritizing natural fibers in my wardrobe continues to be worth the effort. And my distaste for getting dressed in the winter is eternal.
Now tell me about what you’re wearing these days!
xo Harling
I have to say, the whole sock thing has really blown my mind. I've always been very utilitarian with my socks (like white, under armor, anklet) but I bought a pair of grey alpaca/cashmere blend tall socks and I'm obsessed. They look great when my ankles peak out of my jeans. They're so much warmer. I feel fancier and more put together! Especially at friends houses with the no-shoes rule. Like socks are now part of the outfit. A new world has been opened to me!
Why have I never thought to layer one of my many red vintage tshirts under one of my many gray sweaters? 🤯 I love your long vintage coat in that last shot. That is such a beautiful color. Congratulations!