21 Plus-Size Winter Maxi Dresses for When You’re Tired of Wearing Pants

Maggie Griswold
21 Plus-Size Winter Maxi Dresses for When You’re Tired of Wearing Pants
Photo: Allison Kahler.

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During the winter months, I pretty much live in jeans and leggings. Occasionally, I’ll hit the office in a pair of dressier pants, but for the most part, I’m squeezed into tight-fitting denim and spandex. And sometimes, I just get tired of it. If your legs are also begging to be freed—but still covered, because it’s cold out there—cute plus-size winter maxi dresses are here to answer all your sartorial prayers.

Maxi dresses are great for so many reasons, but during winter, they’re the ideal outfit for when you just don’t want to wear pants anymore. You can free your legs from their skinny jean prisons while, at the same time, keeping them away from the cold. It’s a win/win situation all around. Styling maxi dresses for winter is so simple, too. Just pair any maxi dress with a cute puffer coat and boots or high-top sneakers, and you’re in business. Legs are freed, but you’re still feelin’ cozy.

Plus, maxi dresses look good on literally everyone. If you feel like you can’t wear something just because you wear plus sizes, I’m here to tell you that you’re wrong as hell, babe. I’ve shied away from so many styles (TBH, I still do sometimes) just because I was afraid other people would think, “Oh, she shouldn’t be wearing that. She’s too fat for that outfit.” But you know what? I’m done with that fatphobic shit. We all deserve to wear whatever we want—and to feel amazing while doing it.

So don’t shy away from winter maxi dresses, loves, because I’ve rounded up 21 of them. They’re all cute, and a bunch of them can transition into spring—just remove your coat and add some sandals. You’re gonna look amazing all year long.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Glamorous Curve Maxi Dress with High Neck, $79 at ASOS

The neutral colors in this dress are so pretty I could cry.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Kyra Maxi Smock Dress, $37.70 at Elvi

The bow at the neck of this dress just adds a lil ~somethin’ somethin’~.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Modcloth x Anna Sui Rooted in Retro Maxi Dress, $119.99 at Modcloth

Right out of your ’70s fashion dreams.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Kimono Pleated Maxi Skater Dress, $60 at ASOS

Getting so many witchy vibes.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Bat-Sleeve Maxi Dress, $255 at JIBRI

Parrot not included (but we wish it was).

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Misty Floral Maxi Dress, $119 at City Chic

I’m genuinely obsessed with the sleeves on this dress.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

M-Slit Maxi Dress, $35 at Forever 21

Deep V and side slit: two things I love to see in a dress.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

John Zack Wrap-Front Maxi Dress, $87 at ASOS

Everything about this dress is swoon-worthy.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Mid-Sleeve Mock-Neck Flare Maxi Dress, $230 at JIBRI

So many accessory possibilities! (Or go monochrome, if that’s your jam.)

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Everlasting Impression Maxi Wrap Dress, $119 at Modcloth

I would buy this dress 10 times.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Maxi Dress with Cape Back and Dipped Hem, $72 at ASOS

This dress is prettier than I am.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Black Grid Challis Maxi Shirtdress, $88.90 at Torrid

I’ve been looking for a shirtdress this cute my whole life.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Printed Wrap Maxi Dress, $139.90 at Eloquii

Pair this with some brightly colored boots, and you’ll be an instant fashion icon.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Cross-Back Maxi Dress, $35 at Forever 21

Perfect for date night (or mirror selfies).

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Glamorous Curve Maxi Shirtdress, $67 at ASOS

Can’t let Cruella de Vil get her hands on this Dalmatian dress.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Midnight Maxi Dress, $99 at City Chic

You can wear this dress any season of the year.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Velvet Boatneck Maxi Slouch Dress, $280 at JIBRI

This dress screams high fashion.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

PrettyLittleThing Tie-Side Wrap-Front Maxi Dress, $64 at ASOS

You’ll look like a nature goddess.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Blissful Beginnings Floral Maxi Dress, $79.99 at Modcloth

This green deserves heart eyes ONLY.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Wrap Maxi Dress in Zebra Print, $37.70 at Elvi

Hear me out on this one. Add tights or over-the-knee boots and a neon puffer. It’ll look amazing.

STYLECASTER | Plus-Size Winter Maxi Dress to Shop

Daisy Street Smock Dress, $32 at ASOS

The kind of dress you can make casual or fancy, (Just switch between sneakers and heels!)

 

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