These 24 Midi Dresses Will Help You Create Some Ultra-Comfy and Chic Winter Looks

Show off your back in an elegant way in this Nasty Gal Knitted Ribbed Midi Dress ($18, originally $59), which features a high neck, a relaxed silhouette, and long sleeves. Style it with strappy heels for date night.

This Nasty Gal Ribbed Wrap Panel Midi Dress ($18, originally $60) feels like a Sunday dress with its easy elegance and comfort, don't you agree? It's made in a stretchy ribbed jersey that will make it a joy to wear. At home, pair it with slippers or bring out your favorite kitten heels or boots if you have to step out.

This pop-inspired Nasty Gal Abstract Check Mesh Funnel Neck Midi Dress ($24, originally $79) is effortlessly cool, plus the silhouette is easygoing, so you'll be wearing it on repeat. Make it edgy with chunky boots and a leather jacket.

This Line & Dot Camilla Knit Ribbed Shirt Dress ($69, originally $99) is an earthy spin on your traditional shirt dress, and we love the rich yet understated color. Complete your outfit with sneakers or loafers for casual runs.

Reserve this OPT Gertie Dress ($82, originally $137) for dressy occasions like a hot date or office party. The asymmetrical cutout is unexpectedly playful, definitely dialing up the allure. Pair it with tall heeled boots or strappy heels.

On days when dressing up isn't the priority but you'd still like to look effortlessly put-together, this Nasty Gal Notch Neck Ribbed Knitted Midi Dress ($14, originally $45) is the answer. It features a crew neckline with notched detailing, a fitted yet stretchy silhouette, and long sleeves.

This Nasty Gal Recycled Ribbed Knitted Cut Out Midi Dress ($15, originally $89) is cut in a soft fabric and features an unexpected bodice cutout that amps up the sex appeal. We guarantee you'll be repeating this outfit!

This Line & Dot Sylvie Sweater Dress ($77, originally $110) features thigh-high side slits and a one-shoulder neckline with a ribbed panel for a sleek, asymmetrical ensemble. It works both for daytime and nighttime outings.

This sleek Wayf Split V Ribbed Midi Dress ($51, originally $138) features a flattering cutout neckline that makes it irresistibly chic. Finish the look with a wool coat and low heeled sandals.

This sultry Significant Other Monza Cutout Jersey Midi Dress ($220) features front cutouts, signature drapery, and a slim fit, perfect for cocktails on a roof. It has an understated elegance that makes it ready for your next date or vacation night out.

This ASTR the Label Twist Front Long Sleeve Sweater Dress ($89) will charm everyone at the next brunch party or office gathering. We love the neckline and fitted rib fabric.

If you want a professional-looking dress that is also stylish, we found your match. The Good American Long Sleeve Polo Midi Dress ($104, originally $149) is easy to dress up with heels and down with sneakers. Plus, the rib-stitched material makes it comfortable enough to wear all day.

This ASTR the Label Long Sleeve Side Slit Sweater Dress ($79) features a side slit that dials up the allure (and sass). We love the cold-weather-friendly ribbed fabric and mock-neck silhouette.

This Minkpink Willow Ruched Jersey Dress ($90, originally $129) will accentuate your figure, thanks to its lustrous knit and slinky silhouette. It will look great with mules or kitten heels.

The gauzy mesh fabric of this AFRM Shailene Long Sleeve Mesh Dress ($88) dials up the sex appeal. Save it for a chic dinner or an exciting first date.

This H&M High-Sheen Dress ($25) has a certain regal elegance, thanks to the choice of purple, shimmering fabric, and easygoing fit.

This Old Navy Rib-Knit Cardigan Sweater Midi Dress ($40, originally $45) is the answer to slow weekends where comfort is the number one priority. You can leave it unbuttoned over a T-shirt and jeans or wear it as a dress. Either way, you get a two-in-one look.

This Enza Costa Silk Rib Angled Neck Midi Dress ($225) oozes sex appeal, confidence, and femininity. It's a great one to dress up or down, depending on the occasion.

In a sea of wrap dresses, this Nasty Gal Wrap Front Satin Midi Shirt Dress ($30, originally $99) will definitely stand out. Cut in gleaming satin that will nicely hug your body without making you feel restrained, it will pair well with heels and a chunky gold necklace.

This sun-drenched Jonathan Simkhai Mabel Chain-Detailed Cutout Crepe Midi Dress ($323, originally $645) makes a luxuriously elegant and fluid choice for family affairs, dinner parties, or intimate reunions. We love the chunky gold chain embellishing at the waist cutout, as well as the asymmetric silhouette.

This Norma Kamali Slip Dress ($109, originally $165) is a covetable style, designed in a luxurious-looking velvet and drenched in an eye-catching shade of pink. Norma Kamali has, in fact, made the perfect velvet party dress.

This & Other Stories Off Shoulder Tulle Midi Dress ($249) looks straight out of a fairy tale with its voluminous neckline and air of royal elegance. Save it for a fancy gala or a themed holiday party.

This lustrous Self Portrait Lace-Detailed Taffeta Midi Dress ($555) is cocktail ready. It features slightly dramatic puff sleeves, a pleated bodice, and ruched detailing for a flattering fit and polished look.

The green jewel tone of this J.Crew Open-Back Silk Charmeuse Dress ($328) gives it a luxe appearance, while the side slit amps up the sex appeal. It also features a head-turning open back, which makes it an all-around irresistible look.