Dressing While Pregnant: Some Items I've Worn and Loved

A dispatch from 35 weeks.

After I shared that I was pregnant on Instagram, an editor reached out and very kindly asked if I would put together a roundup of “the coolest luxury maternity clothes” for her publication. I was grateful she thought of me but couldn’t help chuckling as I wrote back and explained why that might by tricky. Cool? Luxury? Maternity clothes?? I wish!

By then I’d spent enough time exploring the maternity clothing landscape to understand it is somewhat of a wasteland. Save for a 2-pack of T-shirts Hatch sent me during my second trimester (which I was admittedly overjoyed to receive), I have not worn or purchased any maternity clothes while pregnant. Being straight-size made that easier to manage, as did having a generous wardrobe to begin with. I want to be very clear about the impact of those privileges before diving into some thoughts and suggestions, because while it may be ideal from a sustainability perspective to shop for bump-friendly pieces from within your own wardrobe or to size up in a few pairs of pants that you know you’ll be able to continue wearing with a belt postpartum, that’s not always realistic.

It’s worth acknowledging the limitations of my point of view here for what I imagine is the same reason there are sadly so few compelling brands that bother catering to pregnant women: Pregnant bodies come in infinite shapes and proportions — even within the span of a single gestation — which means there’s no one-size-fits-all approach. Likewise there is no shame at all in buying some soft maternity bike shorts or a delicious, tent-y dress and wearing those things on repeat. Pregnancy can be uncomfortable for so many reasons — your clothing shouldn’t be one of them.

With all of that said, I’m sharing some of the things I’ve worn and loved most throughout pregnancy below. While I’ve really enjoyed the process of figuring out how to style older pieces in my closet during this time, I decided to focus mostly on newer or currently available non-maternity items in order to make this newsletter as shoppable as possible. There is so much to say about this topic and I’m sure I’ll write more about it in the future. If there are certain angles you would like to see it approached from, or specific questions you have, let me know in the comments.

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1. Stretchy black over-the-bump pants

These stretchy, super high-waist pants I got last summer from Leset have been a pregnancy wardrobe gem for two very specific reasons. First of all, even though it’s a synthetic, the fabric is quite nice — thick and almost structured, despite being stretchy. The legs don’t cling too much, so they don’t look like athleisure, but the top band holds you in in a comforting way, especially when you’re pregnant. Secondly, they are aggressively high-waisted. This is critical for me from a pregnancy standpoint, because regular high-waisted things tend to hit at a weird spot on my bump, which doesn’t always look right aesthetically and can feel uncomfortable.

Fit notes: I have my normal pants size (medium), and they continue to fit me even now at the end of my third trimester.

Shopping notes: Leset doesn’t appear to make the exact style I have anymore, but this pair ($210) looks almost identical (I’m pretty sure the only difference is that there are slits at the ankle), and I think these ($128) are the same ones on sale at SSENSE. The waist doesn’t look as high in the photos, but I’m guessing that’s just how they’re sitting on the model. My exact pair without the ankle slits are available here ($100) new-with-tags on Poshmark in a size XL.

Styling notes: I’ve worn these with everything from oversized sweaters and loafers to blazers and ankle boots, but my favorite way to style them is with an extra long button down and a cropped cardigan like this ($99.50). Something about the proportions of this combination really clicked.

2. 100% cotton chinos in a punchy color

During pregnancy I found that bright solid colors often suited me better than statement patterns when styling a more maximalist look. The combination of a traditional chino silhouette with this shade of bright, punchy blue is delightful, and these particular chinos happen to be a lovely weight with a soft, lived-in feel. Very vintage-y, “old J.Crew” vibes, and about as close as you can get to the experience of wearing sweatpants while still remaining firmly in buttons-and-zippers territory.

Fit notes: I sized up in these from a 28 to a 29 and they fit me up until the end of my second trimester. I plan to wear them belted postpartum.

Shopping notes: Still available ($53.99). It looks like the blue color recently sold out, but you can find it secondhand on Poshmark (size 32 for $58 and 28 for $60) and eBay (size 29 for $55). I love the currently in-stock hot pink color in addition to the more neutral options. I’m thinking of buying another pair now that they’re on sale and will probably get the white.

Styling notes: A crewneck sweater or cardigan and ballet flats was my go-to combo.

3. Low-rise baggy Jeans

I went to a press appointment for the denim brand Still Here when I was at the very end of my first trimester. The founder, Sonia, was also pregnant at the time — in fact she was literally about to go to the hospital to give birth when I arrived. Before she left she told me I should take home a pair of the Subway jeans. “Perfect for pregnancy,” she said. I tried them on in the store and wasn’t sure. Ultra baggy with carpenter paneling, they weren’t exactly my usual denim style… fast forward 22 weeks later and I basically want to name my child after them. That’s the funny thing about pregnancy. It inevitably shifts your aesthetic in addition to your shape. I imagined myself living in empire-waist dresses while pregnant, but those types of silhouettes rarely feel quite right whenever I’ve tried them on — too feminine alongside the overt femininity of pregnancy. Contrast is imperative, and these jeans provide exactly that. They also happen to be really well-made, and the denim is downright buttery.

Fit notes: I sized up in these from my usual 28 to a 29 and they fit me until the beginning of my third trimester. I’m excited to reunite with them postpartum when I imagine they’ll provide exactly the right amount of contrast to all the milky softness of that stage as well. If you live in New York, you can always stop by their store in Nolita to figure out your best size.

Shopping notes: Available at full price on Still Here’s website ($260) in every color and size. On sale in black here ($97.50), in classic blue (the color I have) here ($78), in indigo here ($130), and in a few colors here ($120 - $200) secondhand.

Styling notes: I usually gravitate toward more delicate tops since the jeans already exude a sturdy, rough-and-tumble vibe, like a vintage white eyelet blouse or lace-trimmed silk tank, but they also look great with a crisp button down, loafers, and black velvet hair bow.

4. A stretchy crochet skirt

My crochet skirt from SEA is the only skirt I owned previously that has fit me through my entire pregnancy. The beauty of crochet is that unlike many stretchy materials it also happens to look polished and interesting and intricate, which probably explains why this skirt became an unexpected staple as my body grew.

Fit notes: I have my normal size in skirts (medium) and it still fits me now at 35 weeks when I wear it on my hips below the bump.

Shopping notes: My exact skirt is on sale at SEA here ($357) with one size left (XL). There are lots of similar alternatives, though. Here’s a vintage one (size M-L, $90) on Etsy, a handmade one ($129.50) on Etsy, a fun green one from Boden ($90), a striped fringed one on Poshmark (size M, $105) a shorter option ($178) from Reformation, and a maxi ($350) from ba&sh.

Styling notes: I like to style mine with a white crochet top for a coordinated look, but it also looks great with a T-shirt or button down and blazer with loafers or fisherman sandals.

5. Dresses that hug you back

As I explained earlier, most of my usual flow-y, empire-waist dresses don’t feel i.e. look right to me during pregnancy. Silhouettes that are more fitted through my waist and hips work better, but since I’m not really a bodycon girl (by bodycon I’m referring to styles like this), I’ve had to experiment a bit. My favorite pregnancy-friendly dresses have been: a cotton dress with a smocked bodice and full skirt from Modern Citizen, a cotton henley-style dress from Dôen, a pink bias-cut tank dress with a subtle print that I bought at a shop in Venice last summer, and an old Christopher Kane silk slip dress. None are classically “bodycon,” but all of them hug my pregnant body in a way that looks sleek and proportionally suitable.

Fit notes: I have a size small in the Modern Citizen dress and it still fits me at 35 weeks pregnant. Pre-pregnancy I was typically between a small and a medium in dresses, so this particular piece is very accommodating. I have a size medium in the Dôen dress which also still fits me. The Christopher Kane dress stopped fitting me around the end of my second trimester. I got it pre-pregnancy but if I was buying a slip specifically to wear while pregnant, I would probably size up at least one size and plan to wear it belted or a bit oversized postpartum. Oh, and the pink bias-cut tank dress still fits! I just tried it on to double check.

Shopping notes: The Modern Citizen dress ($138) and Dôen dress ($138) are both current and in-stock. Even though the Christopher Kane slip dress is old, I mention it so you can file away “slip dress silhouettes” (which can be great for pregnancy) and “Christopher Kane” (a brand that happens to have a lot of cool silk slip dresses) in your mental pregnancy style cabinet. I love this one (size 4, $276) currently for sale on The RealReal so much I almost bought it myself but as I shared last week I’ve already maxed out my impulsive newsletter research shopping quota of the month. Similarly, “bias-cut” is also a great search term to file away for pregnancy shopping. Bias-cut means that something was cut on the grain rather than following the straight line of the weave, which lends fabric a bit more give and also allows it to drape in a really fluid, beautiful way even when a garment isn’t sharply tailored. This vintage bias-cut dress ($70) would look so chic with thin-strap heeled sandals or espadrilles, a light black silk blazer, red lipstick, and slicked-back hair with a low bun… not to get too specific or anything 😁.

Styling notes: Simple accessories do the trick when it’s warm: a fun handbag, earrings, maybe a hair scarf. If it’s cold, add a blazer or — depending on the dress — a tissue-weight long-sleeved T-shirt layered underneath. A ribbed cardigan, oversized but lightweight crewneck sweater or classic trench coat works too. Avoid adding bulky layers. The adjectives we’re going for here are “fitted” and “streamlined.”

6. Overalls

I wore my vintage pinstriped overalls constantly throughout my first and second trimesters. They still fit with ample room to spare, but I’m wearing them a bit less now that it’s insanely hot and humid in New York and my legs require the freedom to breathe. I’m sure I’ll be reaching for them again as soon as it gets a bit cooler, especially because they’re breastfeeding-friendly.

Fit / Shopping notes: The brand of my vintage pair is Big Smith, which you can find in spades on Etsy and eBay. They’re sized based on an inseam and waist measurement. Mine have a 44-inch waist and a 29-inch inseam. Here’s a pair with a 38-inch waist and 30-inch inseam ($45) and a pair with a 42-inch waist and 34-inch inseam ($32.50). Search “vintage big smith overalls” for other sizes.

Styling notes: My favorite cold-weather overalls pairing is a big-collared blouse underneath a navy crewneck sweater and loafers. For warmer weather: a white ribbed tank top, pearl necklace, and ballet flats.

7. Miscellaneous tops

I won’t spend too much time talking about tops because I think it’s probably the easiest category of clothing to shop for during pregnancy, even if you’re eschewing maternity wear. The types of tops I’ve worn and liked the look of the most were:

• Button downs. A no-brainer. I have a few from Chava Studio that I’ve lived in during pregnancy, styling them with black stretch pants or silky pajama pants with an elasticized waist and lots of jewelry. I’ve especially loved their Infinity Collar Shirt ($350) while pregnant because it’s extra long but still fitted at the top. If you don’t own any button downs or if your pre-pregnancy button downs are more tailored and no longer fit comfortably, there are a lot of great vintage options on Etsy like this blue and white striped cotton one with a mandarin collar ($19.50), this red silk beauty ($41) and this classic white Ralph Lauren with a particularly chic large chest pocket ($52). Alternatively, if you happen to cohabitate with a man who wears a larger size than you did pre-pregnancy, you could also steal some of his.

• A short-sleeve cotton poplin wrap top. A fantastic pregnancy silhouette, but important to find one with a tie that wraps all the way around like this ($75) instead of just tying at the side so you can really cinch it above the bump. I have an old one from Sabina Sommer that I’ve worn mostly with black stretchy pants, the J.Crew trousers, or elastic-waist shorts.

• Long-sleeve crochet tops. I owned two before getting pregnant (a vintage one and an old Ulla Johnson one), and they both still fit me now in my third trimester. I love them for the same reason I love the crochet skirt. Polished stretch!! I’ve worn them interchangeably with my crochet skirt or with jeans. I like this vintage one ($35) on Etsy.

• The aforementioned HATCH maternity T-shirts ($98 for 2). It was really nice to have some legit maternity T-shirts that were fitted up top but long and big enough at the bottom to go all the way over the bump so that I didn’t resemble Winnie the Pooh. It’s hard to find normal-looking 100% cotton maternity T-shirts because a lot of them are too fitted or have weird ruching on the sides or have “mama” embroidered on the chest (I’m serious). I liked that these were clean and classic and looked like T-shirts I would wear outside of pregnancy. They run a bit small and I wish I’d sized up from a 2 to a 3, but I’ve still worn them everywhere / with everything.

xo Harling