29 Stunning Plus-Size Dresses for All the Winter Festivities Ahead

Calling all plus-size fashion people: I've found the perfect dress for all your cold-weather moods. As a plus-size fashion editor, I know firsthand how difficult it can be to find the right outfit, let alone a dress to fit the occasion. But for this winter season, I've got you covered. Since shopping is my job, I've sifted through some internet hotspots to bring you some gorgeous dress finds fit for any of the winter festivities you have planned.
Are you in need of a formal gown for an upcoming wedding? Perhaps you need a cute, casual sweater dress for a holiday potluck. No matter the reason, I've found pieces to help you take on whatever the Winter has in store. Keep scrolling to uncover my finds from retailers such as Anthropologie, Wray, H&M, and many more.

Chinazor "Chichi" Offor is a Georgia-born, Los Angeles–based associate editor who relocated from Brooklyn, New York, and joined Who What Wear's West Coast office in 2022. At WWW, she utilizes over 10 years of editorial experience to dish out shopping advice to the masses and analyze key pop-cultural moments. Chichi previously worked at Refinery29, where she helped revolutionize the brand’s plus-size and inclusive fashion coverage. In her spare time, she’s keeping up with the latest movie releases, enjoying a relaxing day at the spa, or obsessing over her latest ADHD-fueled hyperfixation (e.g., Jesse McCartney's underrated career, the negative effects of bicoastal intellectual elitism, and Gen Z’s loneliness epidemic). You can find her online @thechichio on Instagram.
-
From Engagement to Holiday Parties, My Closet Is in Need of Some Fancy Dresses—32 Chic Options I'm Eyeing
Here are the standouts.
-
I'm a Bridal Stylist—These Are the Best Fall Wedding Guest Dresses Under $500
The couple is sure to approve.
-
It's Boho Chic on a Budget—29 Gorgeous Free People Sale Finds I'm Absolutely Loving
Up to 70% off!
-
5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This Fall
Take notes.
-
Fine, I Won’t Gatekeep—These 27 Abercrombie Finds Are Too Chic to Miss (and They're All On Sale)
I can't decide which fall pick is my favorite.
-
I'm a Senior Shopping Editor—Here Are 30 Fall Finds That I'm Hands Down Most Excited About Right Now
Get ready to answer, "Where'd you get that?"
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?