What to Wear for the Holidays When You’re Pregnant or Postpartum

Q: What should I wear for holiday events during pregnancy?

Look for comfortable silhouettes such as slip dresses, cardigans worn as tops, layered lines, and outfits that elongate the body. Pieces that can be layered and adjusted as your bump grows make pregnancy holiday outfits feel both festive and comfortable.

Q: How do I dress for postpartum when nothing fits right?

During postpartum, start with elevated basics in soft fabrics and then add structure with a jacket, bag, or belt if that feels comfortable. Slip dresses, oversized tees, and easy layers are forgiving, flattering, and can evolve with your changing body.

Q: What outfits are best for postpartum holiday gatherings?

Slip dresses layered with tees or knits, stretch pants with a cardigan-as-top, and button-downs with slimmer bottoms or tall boots are great postpartum holiday outfit ideas. They balance comfort, movement, and style while making it easier to nurse or pump if needed.

Dressing for a new body can be difficult—especially during the holidays, when you want to feel festive but may not feel like your bod is fitting the way it once did. We’ve been there, we are there, and we’re lucky to have friends like stylist Kelly Klein who can help us.

We brought together two of our favorite Mamalas— stylist Kelly Klein (@kellyklein__) and dietitian Lauren Steiner (@osoanutrition)—one to dress and one to be dressed—to give us the inspiration we’re craving for getting dressed (and feeling our best) this holiday season. Whether you’re pregnant, postpartum, or somewhere in between, these outfit ideas meet your body where it is today.

The theme is simple: look good, feel good. Two things can be true—healing happens from the inside out (good nutrition) and from the outside in.

TLDR:

Holiday lunch: layered lines
Cocktail party: cardigans as tops
Playdate: elevated basics
Holiday drinks: find balance
Family gathering: the slip dress

For a Holiday Lunch: Layered Lines

Kelly’s Tip: “Keep the front open so the shape of the jacket or shirt creates two clean lines down the body. It naturally frames the bump in a way that feels balanced without doing anything extra.”

Lauren wears a midi slip dress with a cropped button down layered under a heavier cotton light jacket (or this as a cheaper alt) with a knee high boot.

For a Cocktail Party: Cardigans as Tops

Kelly’s Tip: “A cardigan can easily act as a 'date night top'. Unbutton your cardigan to the bra line to create a natural v-neck. As your boobs get bigger in pregnancy, a more open neckline gives your growing boobs space, so the outfit doesn’t feel heavy or crowded up top*.”

Lauren wears stretch pleated pants and a lightweight cardigan with a chunky heel.

*Pumping/breastfeeding? Gives you an easy access option to breasts.

For a Holiday Playdate: Elevated Basics

Kelly’s Tip: “If you’re in softer pieces (tees, stretchy pants, knits), bring in something with structure to ground the look. Some pieces that do this could be a jacket, a bag, or if you’re not pregnant then a belt. That small hit of structure instantly sharpens everything and adds shape and interest. It’s the easiest way to elevate simple pieces and make the outfit feel intentional again.”

Lauren wears an ecru jean, oversized T-shirt with monochromatic sweater (or a sweatshirt would work)and clog of the same color scheme.

For Holiday Drinks: Find Balance

Kelly’s Tip: “Slimmer bottoms (or a tall boot with shorts) help balance the bump. Because there’s more volume through the middle, a slimmer leg keeps the outfit looking balanced and not bulky.”

Lauren wears a button down with bejeweled buttons that is oversized, with barely visible shorts (add tights) and a knee high boot.

For a Family Gathering: The Slip Dress

Kelly’s Tip: “A slip dress is a great staple during pregnancy and postpartum (and always frankly). It’s an easy one-piece base you can style a dozen ways. Wear it on its own, or layer it under a tee, a knit, or a jacket. It’s one of those pieces that does a lot of work for you. Here, we layered a t-shirt on top and added a kimono over it for some movement.”

Lauren Wears a slip dress layered with an oversized tshirt , and Kimono, knee high boot.

Want More of Kelly's Dressing Tips To Look/Feel Your Best?

Read: Kelly's complete guide: 8 Tips for Pregnancy and Postpartum Dressing

Subscribe to Kelly's Substack: https://kleinkelly.substack.com for the best styling tips, outfit ideas, and creative ways to get dressed

Looking for a Sustainable, Balance, and Individualized Approach to Health?

Follow and reach out to Lauren here - she is an incredible Registered Dietitian and Functional Medicine Nutritionist.

P.S. If you’re in the pregnancy or postpartum season and want support from the inside out, explore our Support Snacks™—organic, functional snacks formulated for recovery, hormone health, and real-life energy.

👉 https://www.mamalaorganics.com/collections/support-snacks