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Best Winter Midi Dresses 2022 | Shopping Guide

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

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Midi dresses may not immediately come to mind for cold-weather dressing, but there are plenty of fresh and creative ways to turn them into winter-friendly ensembles. The key is to look for the midi dresses that are made in warm materials (can't go wrong with wool, velvet, or knit) or pair them with practical layers that will keep you snug. Finding the right winter midi dress is half the battle, so we went looking for covetable styles that don't sacrifice comfort or warmth.

The Enza Costa Silk Rib Midi Dress will look great paired with tall heeled boots for date night, while the Good American Long Sleeve Polo Midi Dress will garner tons of compliments upon your return to the office. Scroll on for more options that will suit every budget.

Image Source: Nasty Gal

An Open Back Statement: Nasty Gal Knitted Ribbed Midi Dress

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

Image Source: nastygal.com
Nasty Gal Knitted Ribbed Midi Dress
$18
from nastygal.com
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A Sunday Dress: Nasty Gal Ribbed Wrap Panel Midi Dress

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

Image Source: nastygal.com
Nasty Gal Ribbed Wrap Panel Midi Dress
$18
from nastygal.com
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A Funky Print: Nasty Gal Abstract Check Mesh Funnel Neck Midi Dress

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.

Image Source: nastygal.com
Nasty Gal Abstract Check Mesh Funnel Neck Midi Dress
$24
from nastygal.com
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A Comfy Line & Dot Camilla Knit Ribbed Shirt Dress

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 colour. Complete your outfit with sneakers or loafers for casual runs.

Image Source: shopbop.com
Line & Dot Camilla Knit Ribbed Shirt Dress
$69
from shopbop.com
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A Special Occasion OPT Gertie Dress

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.

Image Source: shopbop.com
OPT Gertie Dress
$82
from shopbop.com
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A Busy Day Match: Nasty Gal Notch Neck Ribbed Knitted Midi Dress

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.

Image Source: nastygal.com
Nasty Gal Notch Neck Ribbed Knitted Midi Dress
$14
from nastygal.com
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An Outfit Repeater: Nasty Gal Recycled Ribbed Knitted Cut Out Midi Dress

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!

Image Source: nastygal.com
Nasty Gal Recycled Ribbed Knitted Cut Out Midi Dress
$15
from nastygal.com
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A Day-to-Night Ensemble: Line & Dot Sylvie Sweater Dress

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

Image Source: shopbop.com
Line & Dot Sylvie Sweater Dress
$77
from shopbop.com
Buy Now

A Flattering Wayf Split V Ribbed Midi Dress

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.

Image Source: saksfifthavenue.com
Wayf Split V Ribbed Midi Dress
$51
from saksfifthavenue.com
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A Seductive Style: Significant Other Monza Cutout Jersey Midi Dress

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 holiday night out.

Image Source: modaoperandi.com
Significant Other Monza Cutout Jersey Midi Dress
$220
from modaoperandi.com
Buy Now

A Day-to-Night Look: ASTR the Label Twist Front Long Sleeve Sweater Dress

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.

Image Source: nordstrom.com
ASTR the Label Twist Front Long Sleeve Sweater Dress
$89
from nordstrom.com
Buy Now

An Office-Ready Dress: Good American Long Sleeve Polo Midi Dress

If you want a professional-looking dress that is also stylish, we found your match. The Good American Long Sleeve Polo Midi Dress ($78, originally $104) is easy to dress up with heels and down with sneakers. Plus, the rib-stitched material makes it comfortable enough to wear all day.

Image Source: nordstrom.com
Good American Long Sleeve Polo Midi Dress
$78
from nordstrom.com
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A Side Slit Entry: ASTR the Label Long Sleeve Side Slit Sweater Dress

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.

Image Source: nordstrom.com
ASTR the Label Long Sleeve Side Slit Sweater Dress
$79
from nordstrom.com
Buy Now

For Maximum Allure: MINKPINK Willow Ruched Jersey Dress

This MINKPINK Willow Ruched Jersey Dress ($90, originally $120) will accentuate your figure, thanks to its lustrous knit and slink silhouette. It will look great with mules or kitten heels.

Image Source: shopbop.com
MINKPINK Willow Ruched Jersey Dress
$90
from shopbop.com
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A Sleek First Impression: AFRM Shailene Long Sleeve Mesh Dress

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.

Image Source: nordstrom.com
AFRM Shailene Long Sleeve Mesh Dress
$88
from nordstrom.com
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Royal Purple: H&M High-Sheen Dress

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

Image Source: www2.hm.com
H&M High-Sheen Dress
$25
from www2.hm.com
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A Weekend Rendezvous: Old Navy Rib-Knit Cardigan Sweater Midi Dress

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.

Image Source: oldnavy.gap.com
Old Navy Rib-Knit Cardigan Sweater Midi Dress
$40
from oldnavy.gap.com
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Some Cutout-Shoulder Action: Enza Costa Silk Rib Angled Neck Midi Dress

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.

Image Source: amazon.com
Enza Costa Silk Rib Angled Neck Midi Dress
$225
from amazon.com
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A Red Hot Moment: Nasty Gal Wrap Front Satin Midi Shirt Dress

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.

Image Source: nastygal.com
Nasty Gal Wrap Front Satin Midi Shirt Dress
$30
from nastygal.com
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A Yellow Pop: Jonathan Simkhai Mabel Chain-Detailed Cutout Crepe Midi Dress

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 the waist cutout, as well as the asymmetric silhouette.

Image Source: modaoperandi.com
Jonathan Simkhai Mabel Chain-Detailed Cutout Crepe Midi Dress
$323
from modaoperandi.com
Buy Now

An Absolute Stunner: Norma Kamali Slip Dress

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.

Image Source: amazon.com
Norma Kamali Slip Dress
$109
from amazon.com
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A Dreamy Moment: & Other Stories Off Shoulder Tulle Midi 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.

Image Source: stories.com
& Other Stories Off Shoulder Tulle Midi Dress
$249
from stories.com
Buy Now

A Taffeta Affair: Self Portrait Lace-Detailed Midi Dress

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.

Image Source: modaoperandi.com
Self Portrait Lace-Detailed Taffeta Midi Dress
$555
from modaoperandi.com
Buy Now

A Green Statement: J.Crew Open-Back Silk Charmeuse Dress

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.

Image Source: jcrew.com
J.Crew Open-Back Silk Charmeuse Dress
$328
from jcrew.com
Buy Now

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