Shopping·8 min read

Winter Dresses for Any Occasion Under $150

Winter Dresses
Design: theSkimm | Photos: Free People, Abercrombie & Fitch
January 3, 2024

Products you buy through our links may earn us a commission. Oh, and if something's out of stock, oops, it was there (and all prices were accurate) at time of publication.

The weather outside may be frightful, but your outfits can still be delightful. If the temps are dropping and you have somewhere to be — a party, office gathering, or date night — we’ve got you covered (literally). We’ve pulled together winter dresses to keep you feeling warm and looking chic, no matter your budget. From long-sleeve dresses great for layering to pretty velvet numbers for winter weddings, these pieces will keep you stylish til spring.

Winter dresses under $50

Winter Dresses

A soft and breathable rib-knit dress you can wear into spring…

This one has a classic scoop neck and a mini back slit. It comes in five colors and is easily layerable. Try it paired with a cropped cardigan or light jacket and your favorite tights. It’s made with Tencel, a biodegradable fabric that’s even more breathable than cotton, so you won’t sweat when the heat is on full blast. ($49.90, Quince)

Buy it
Winter Dresses

A cable-knit sweater dress meant for accessorizing…

This simple sweater dress is begging to be paired with tights, knee-high boots, belts, winter hats...the accessorizing opportunities are endless. It comes in over 20 colors and has a slightly oversized fit, so you’ll be comfortable all day long. We’ve even traveled in it and can confirm it passes the plane test. ($49.99, Amazon)

Buy it

A classic slip dress that looks way more expensive than it is…

Okay, Target, we see you. We would believe you if you told us this dress came from a fancy department store. The silhouette is just right, from the V-neck to the side slit for movement when you walk. It’s perfect for a winter date night — just add a leather blazer or layer a turtleneck on top. ($25, Target)

Buy it

A velvet gown you’ll wear for years…

This velvet gown is exactly what your evening wear collection is missing. Every detail ensures it’ll fit you like a glove, from the tie at the waist to the ruched bodice and 5% spandex for a stretchy feel. You’ll feel so good in this you’ll want to wear it even when you don’t have a special occasion to attend. Go ahead, wear it out to dinner. ($18.80, Eloquii)

Buy it

Winter dresses under $100

Winter dresses

A wrap dress you’ll want to wear over and over…

This flowy, stretchy number comes in seven different colors and patterns and hits right below the knee. The three-quarter sleeves and deep V-neck make this a stylish closet staple you’ll be turning to again and again. Depending on how you accessorize it, you can wear it for pretty much anything, from holiday parties to nights out with friends to brunch the next day. ($98, Nordstrom)

Buy it
Winter dress

An off-the-shoulder midi dress for date night or a party…

If you’re going for a more formal and elevated look, this dress will be the perfect fit. It has a flattering silhouette and is made from high-quality jersey fabric. The top is fitted then flows into a full skirt, so you’ll be able to move comfortably. Pair it with a shiny clutch and heels for a night out. ($74.40, Reformation)

Buy it

The Skims dress everyone’s talking about…

When Kim Kardashian designs the perfect dress, we don’t ask questions. We’ve tried it ourselves and can confirm: it’s one of the most flattering dresses we’ve ever put on. The ribbed fabric is lightweight and compressive but not restricting, the sleeves will keep you warm, and we love the trendy square neckline. Get ready to have to peel yourself away from the mirror. ($62+, Nordstrom)

Buy it
Free People

A maxi sweater dress that’s as comfortable as wearing pajamas…

Enter: the sweater dress you didn’t know you were missing. Throw this soft turtleneck dress on when you want to look chic while running errands, for brunch, or even for working from home. The wide-ribbed fabric is so comfy, and it looks great paired with everything from boots to ballet flats to sneakers. ($78, Free People)

Buy it

Winter dresses under $150 

Winter dress

A velvet dress with elegant cutouts…

This one comes in two colors — black and burgundy — and just screams “perfect winter wedding guest dress.” We love the eye-catching, one-shoulder design, open back, and thigh-high side slit. And the fact that it’s been produced ethically and sustainably. ($102.40, Marcella)

Buy it
Winter dress

A shimmery number that pulls out all the stops…

Puffy sleeves? Check. Side slit? Check. Disco ball shimmer? Check and check. If you’re looking for a dress that can go from the dance floor to the dining room and turn every head along the way, this metallic one from cult-favorite brand ASTR the Label is it. It’s partially lined and made with ruched jersey fabric for a comfy fit. ($76.80, Shopbop)

Buy it

A turtleneck sweater dress that’s giving us rom-com vibes…

Cameron Diaz in The Holiday, is that you? We’re obsessed with the classic high-neck silhouette of this form-fitting sweater dress. The side slit gives it a bit of an edge and lets you show off your boots, and the sleeveless style is perfect for adding a leather jacket. ($118, Revolve)

Buy it
Abercrombie & Fitch

A long-sleeve maxi dress to get the sheer look…

If you’d like to get in on the sheer trend without actually baring at all, this dress is the one for you. It comes in two styles — with either a lace or mesh overlay — and has a built-in slip underneath so you can amp up the sexy vibes without worrying you’re wearing the right underwear. The high neck will keep you covered, whether you’re bopping on the dancefloor or leaning over to blow out your birthday candles. ($100+, Abercrombie & Fitch)

Buy it

Live Smarter

Sign up for the Daily Skimm email newsletter. Delivered to your inbox every morning and prepares you for your day in minutes.