The Cutest Winter Dresses

Finding cute winter dresses can be tough, right? There are several things to take into account if you live in a chilly location. Not only does it need to keep you warm, it also needs to look cute. If you've struggled to find a dress for your holiday party, to wear to the office, or to wear around the house, look no further. Below are some stylish dress options for casual get-togethers and red carpet events, along with some tips to keep warm and stylish all winter long.  

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Shimmer and Shimmy

David's Bridal Sequined Lace Fit-and-Flare Dress
David's Bridal

Looking for a snazzy dress to wear to a winter wedding or cocktail reception? Try this Sequined Lace Fit-and-Flare Dress available at David's Bridal. The sequins will shimmer as you shimmy on the dance floor, and add some extra sparkle to any big day. Plus, the lace is a beautiful material, especially in this dark burgundy color. And it's just enough coverage to keep you warm and bright. Pair this cute dress with a silver clutch and metallic heels to keep the glam going. This style also makes a great New Year's Eve choice — just add in confetti! 

Style Tip: The lace at the neckline of this dress is slightly sheer. To keep your bra straps from showing, wear a supportive strapless bra in a neutral color. 

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Perfectly Plaid

J Crew Drapey long-sleeve dress in Black Watch plaid
J. Crew

This J. Crew Drapey long-sleeve dress in Black Watch Plaid is perfect for trimming a tree or a winter party RSVP. The long sleeves will keep you warm, while the attractive cut will keep you stylish. Plus, the slightly swingy skirt is begging for a spin on the dance floor. And don't forget the tie at the waist, which gives you an (adjustable) cinching option for a sleek and feminine look. We won't tell if you make it a little looser after some holiday cookies or cocktails. Comfort is key!

Style Tip: Plaid is a classic pattern. To jazz it up a little, try some sparkle! Wear some sparkling earrings or a shiny statement necklace to make this look pop. Plus, a classic bright red lip is a dynamite addition. Winter needs a little burst of color!

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Velvet Va Va Voom

Zara velvet tube dress

It's no secret that velvet is the material of the moment. It's luxe, rich, and dazzling to the touch. It's also especially suited for a cute winter dress because of its warm and fuzzy feeling. And this Velvet Tube Dress from Zara is especially suited for your next winter party. Can't you just see yourself sipping on eggnog in this cute dress? The off the shoulder cut and body hugging fit are so sexy paired with the modest sleeves and longer length. It's a beautiful mix of sexy and simple. Hey, it's good to keep them guessing. 

Style Tip: This red hot color looks great with metallics. Try a dressy evening shoe, bag, or even a belt to add in some winter shimmer. You can also pair it with shimmery eye shadow and a glossy lip. 

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Twinning Is Winning

Palava Made Memorable Midi Dress in Reindeer Modcloth

Got a mini me in your life? This cute dress duo is for you. The Palava Made Memorable Midi Dress in Reindeer from Modcloth is a winner — times two! The deep red color and darling reindeer motif are perfect for the winter months. And there's even a matching dress for a little girl. Alert the mothers and daughters in your life, this is the perfect holiday photo attire. 

Style Tip: This dress combo has a sweet retro flair to it. Pair it with some Mary Jane shoes — which are a cute option for both adults and children. Add in some shimmering or cable knit tights for warmth and you're ready for a winter get-together!

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Bow Beautiful

Eloquii velvet bow dress

This Velvet Fit And Flare Dress from Eloquii is designed especially for plus size women. They have a wide array of dresses for clothing sizes 14 and up, and they range from downright daring to sugary sweet. This cute winter dress is a beautiful combination of the two. You'll be as pretty as a present with the cute bow tie at the neck. And this fashionable velvet print is both rich and on trend. 

Style Tip: Wear this dress with a classic pair of black riding boots for a casual jaunt with your gal pals. Need to dress it up? Try wearing cute black heels for a night out on the town, hand in hand with a special someone. 

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Cozy Winter White

Give Love White Sweater Dress Tobi

For a casual and cute winter dress, cozy up in this Give Love White Sweater Dress from Tobi. Available in other colors, it's really this bright winter white that makes it memorable. The tall turtleneck and knit material will keep you warm on even the coldest snowy winter nights. Meanwhile, the short length and revealing shoulder cut out make things even hotter. Pack a warm wool scarf if you need to keep your shoulders warm. 

Style Tip: Wear this dress over a pair of leggings or even a pair of skinny jeans. Top off the outfit with tall winter boots and you're ready for a ski lodge get-together or a night in by the fire. 

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Lace Long Sleeves

Francesca's lace dress

The Corina Lace Shift Dress from Francesca's offers the stunning combination of a short length with long sleeves. This sexy lace dress is lined throughout the torso to keep things demure, but with sheer lace sleeves for a little peek-a-boo action. And don't miss out on the keyhole back for that extra flash of skin! This cute winter dress is especially great for a date night or a kiss under the mistletoe. 

Style Tip: The short length of this dress will pair well with suede over the knee boots. Or try a pair of booties (so you can sashay through the snow or sleet) with a pair of stockings. Bonus points if there's a sexy back seam or fun print! 

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Sexy Sweatshirt

Hoodie Sweatshirt Dress NY & Co.
NY & Company

Sometimes the most casual dresses are the cutest. Take this Hoodie Sweatshirt Dress from NY & Company for example. It's super cute and available in several colors (pictured here in classic gray). Plus, it's a versatile addition to your winter wardrobe because you can wear it indoors or out. The soft fabric and hood will keep you cozy while you stay inside and cuddle up with your favorite movie and wintertime treat. Or take it for a spin in the chilly air! 

Style Tip: Want to wear this cute dress out? Slip on a pair of leggings, or some over the knee boots for some warmth and coverage. However you style it, you'll be warm and ready for winter!

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Terrific Tulle

ASOS PREMIUM Sheer Top Tulle Mini Prom Dress

3, 2, 1... Countdown to the New Year in this ASOS Sheer Top Tulle Mini Dress. Have someone to kiss at midnight (or looking for someone)? The sheer mesh top and eyelash lace bodice of this cute dress will practically do the flirting for you. Not to mention the come hither open back and sweet little bow. You'll knock 'em dead at your holiday party, for sure. Throw in some heels and a smokey eye for a sultry outfit. And maybe wear your hair up so there's an uninterrupted view of the daring back and bow!

Style Tip: For back baring dresses like this, try wearing an adhesive bra, nipple covers, or going without anything. Whichever you choose, make sure you feel supported and confident! 

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Pretty in Prints

Lulus floral dress

Who says floral print is for spring and summer only? In this I. Madeline Garden Splendor Floral Print Dress from Lulu's, you can bring the floral theme into the colder months. The dark background of this print keeps it from being too summery, while the bold floral print adds a dose of happiness to a gray winter day. Long sleeves, a crew neck, and a midi length make it great for the cold. And the sweet keyhole back and button cuff are cute as can be. 

Style Tip: This outfit looks especially cute with booties or tall boots. Try a motorcycle boot with a chunky heel and harness detail for a little more edge, or keep it dainty with a stiletto heel or pointy toe boot for a more delicate look. You decide!

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Wrapped Up for Winter

Layered Dress Anthropologie Maeve

No need for a coverup with this cute winter dress. The dreamy Layered Arabesque Dress by Maeve, available at Anthropologie, has a built-in wrap sweater on top! It's soft and cozy, and will keep you warm all winter. Plus the pleated skirt is airy and flowy. It's a great option to wear to the ballet, to see The Nutcracker, perhaps? Keep it stylish all winter long with warm tights and a scarf. 

Style Tip: The icy blue color of this dress is a frosty choice for winter and pairs well with silver jewelry or ivory accessories. Try a long necklace that drapes down the torso, or a shiny bracelet. 

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Fairisle Fashionable

Sweater Dress LOFT

After a day of skiing, slip this Fairisle Off the Shoulder Sweater Dress 404 from LOFT on and sit by the fire. You can snuggle up in the soft material, while still staying cute because the foldover off-the-shoulder neckline is very on trend, while the print is perfect for the season. Can't you just see yourself sipping hot cocoa and reflecting on your rides up and down the mountainside in this cute dress? It's also great for a casual get-together with friends or a casual weekend getaway with your honey.

Style Tip: A pair of fuzzy earmuffs or a furry winter hat are great for wearing with this snuggly dress. And if you're wearing it indoors, put on a pair of fuzzy slipper socks or your coziest slippers.