Midi Dresses

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Fall & Winter Midi Dresses You’ll Live In

Welcome your cold‑weather glow with midi dresses that bring warmth and wow. Our curated edit of mid-length dresses blends cozy knit, velvet, satin, and stretch crepe to keep you wrapped in chic style all season long. Dress them up or down—this is the collection that proves midi dresses aren’t just for sunshine.

Winter Nights, Office Days, Holiday Evenings

From formal midi dresses for gala nights to midi holiday party dresses that shine under string lights, we’ve got every vibe covered. Think long sleeves, mock necks, and rich jewel tones for upscale events. When you want a touch of edge, reach for a midi club dresses silhouette with cutouts or ruching that plays up bodycon lines while still delivering mid-length elegance.

Styles That Work Overtime

In our fall/winter midi line, expect figure-flattering details like ruching, wrap waists, off-shoulder necklines, and asymmetric hems. Cozy yet sleek ribbed knits, ponte, and sweater fabrics make daytime wear effortless—pair with a moto jacket or trench. For evening, slip into velvet or satin mid-length dresses that catch candlelight and camera flashes alike. With pockets, adjustable straps, and stretch back panels, each piece solves styling hiccups so you look composed from date to dance floor.

Layering is everything this season—add a cropped faux fur, a tailored blazer, or sheer long-sleeve mesh underneath. Pair with knee-high boots or strappy heels depending on the look. Whether you're heading to the office, a holiday soirée, or dinner with friends, our midi dresses adapt to your schedule and mood.

Fall & Winter Midi Dresses You’ll Live In

Welcome your cold‑weather glow with midi dresses that bring warmth and wow. Our curated edit of mid-length dresses blends cozy knit, velvet, satin, and stretch crepe to keep you wrapped in chic style all season long. Dress them up or down—this is the collection that proves midi dresses aren’t just for sunshine.

Winter Nights, Office Days, Holiday Evenings

From formal midi dresses for gala nights to midi holiday party dresses that shine under string lights, we’ve got every vibe covered. Think long sleeves, mock necks, and rich jewel tones for upscale events. When you want a touch of edge, reach for a midi club dresses silhouette with cutouts or ruching that plays up bodycon lines while still delivering mid-length elegance.

Styles That Work Overtime

In our fall/winter midi line, expect figure-flattering details like ruching, wrap waists, off-shoulder necklines, and asymmetric hems. Cozy yet sleek ribbed knits, ponte, and sweater fabrics make daytime wear effortless—pair with a moto jacket or trench. For evening, slip into velvet or satin mid-length dresses that catch candlelight and camera flashes alike. With pockets, adjustable straps, and stretch back panels, each piece solves styling hiccups so you look composed from date to dance floor.

Midi Dresses in Every Shade—With Holiday Styling Tips

Explore our curated midi collections in every hue, with outfit ideas that transition effortlessly from festive dinners to gift swaps and winter weddings:

  • Black Midi Dresses: Pair a sleek black midi with pointed-toe pumps and a structured blazer for an office party look that turns into dinner-ready elegance.
  • Blue Midi Dresses: Go bold with cobalt blue styled under a faux fur jacket and metallic heels for a festive night out with friends.
  • Green Midi Dresses: Elevate your holiday presence in an emerald green midi paired with gold statement earrings and velvet ankle boots.
  • Pink Midi Dresses: A blush pink midi with soft satin finish and nude heels is perfect for a winter bridal shower or holiday brunch.
  • Red Midi Dresses: Command attention in a scarlet red midi, styled with a faux leather moto jacket and black booties for party-season drama.
  • White Midi Dresses: For winter formals or seasonal celebrations, opt for a white midi layered with a crystal-embellished belt and silver heels.

Shop Windsor’s midi dresses online, in-store, or in-app—and fall in love all over again. From cozy daytime looks to ultra-glam formal midi dresses and midi holiday party dresses, your new go-to mid-length dresses await.

  • Flawless Figure Sleeveless Bandage Midi Dress

    Feel sexy and snatched in this bandage midi dress designed to show off your flawless figure! The midi dress is crafted on bandage seamless knit fabric, offering a bodycon silhouette that hugs your curves just right, wide tank shoulder straps, a V-neckline, and a square-cut back to show some skin. Complete the look in stiletto heels for a date night!

    Fit & Features

    • Sleeveless V-neckline, cross bust design
    • Wide tank shoulder straps
    • Square-cut back, lower hidden zipper, hook and eye closure
    • Bodycon silhouette, midi-length hem
    • Seamless bandage knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1808

    Category Name: Midi Dresses

    Price: $6.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Sweetheart Wrap-Front High Slit Midi Dress

    Create an adorable winter 'fit with this wrap-front midi dress you'll want to wear all season long. It features a V-neckline with a chic surplice wrap-front design, long fitted sleeves, a midi-length hem with a high-cut side slit, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Complete your look with a moto jacket and sleek ankle boots.

    Fit & Features

    • V-neckline, surplice wrap-front design
    • Long fitted sleeves
    • Midi-length hem, high side slit
    • Form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5338

    Category Name: Midi Dresses

    Price: $5.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist Perfection Cutout Sweater Midi Dress

    Showcase this perfect twist sweater midi dress all season! With its form-hugging rib knit sweater fabric, V-neckline, twisted bust, cutout bodice, fitted long sleeves, and side slit, you'll look stylish with every step. Complete the look in booties for day or night!

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Twisted bust, cutout bodice
    • Form-hugging fit
    • Side slit, midi-length hem
    • Rib knit sweater fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1907

    Category Name: Midi Dresses

    Price: $7.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kallie Formal Foiled Metallic Ruched Midi Dress

    Special Occasion

    The Kallie formal ruched midi dress is an iconic style for cocktail hour or an elevated party! Designed from a trendy foiled metallic knit fabric, she features a sleeveless cowl neckline, spaghetti straps, all-over ruched detailing to flaunt your gorgeous figure, a mid-length hem, and a bodycon silhouette. Complete your chic look in this formal dress with rhinestone fringe earrings and strappy stiletto heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • All-over ruching
    • Mid-length hem, bodycon silhouette
    • Foiled metallic knit fabric
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1894

    Category Name: Midi Dresses

    Price: $59.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Beauty Printed High Slit Midi Dress

    You'll fall in love with the abstract beauty of this chic printed midi dress! Crafted from a sheer woven fabric with a full-length knit lining, this mid-length dress features a sleeveless cowl neckline, adjustable spaghetti straps for a customized fit, a partially open back with a cross-back strap design and lower back straps, a high-cut side slit to showcase some leg, a flowy A-line silhouette, and an all-over multi-colored abstract print pattern to catch everyone's eye. Style with a layered necklace and clear heels for a gallery opening!

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Partially open back, cross-back strap design, lower back straps
    • Mid-length hem, high-cut side slit, flowy A-line silhouette
    • Multi-colored abstract print
    • Sheer woven fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5525

    Category Name: Midi Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Only Chic Vibes Ruched Velvet Midi Dress

    This stunning ruched velvet midi dress will bring only chic vibes to your next cocktail party. Crafted from a luxe smooth velvet fabric, this mid-length dress features a sleeveless square neckline, spaghetti straps, ruched detailing at the waist for a figure-flattering look, and a form-hugging silhouette. The velvet fabric offers a moderate stretch. Complete your dressy 'fit with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline, dart seams
    • Spaghetti straps
    • Ruched waist
    • Mid-length hem
    • Form-hugging silhouette
    • Velvet fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2899

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes Moment Sleeveless Midi Dress

    Cue the compliments. With a square neckline and curve-loving ruching, this midi is your ticket to owning the spotlight—effortlessly.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Square neckline
    • Wide shoulder straps
    • Side ruched seams
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000394

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: MAUVE

    Available Size: S

  • Alluring Muse Metallic High Slit Midi Dress

    Stylishly turn heads like the alluring muse you are in this metallic midi dress! It features a sleeveless square neckline, spaghetti straps, an asymmetric mid-length hem creating a sultry thigh-high side slit, and a form-hugging silhouette. The textured metallic knit fabric will give off the most stunning sheen to make sure all eyes are on you. Complete your party 'fit with sparkly rhinestone heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Asymmetric mid-length hem
    • Thigh-high side slit
    • Form-hugging fit
    • Textured metallic knit fabric, sewn-in stretchy knit lining
    • Runs true to size 

    Style Number/Barcode: 05101-2858

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dazzling Night Sequin Cowl Midi Dress

    Experience the glamor of the red carpet in this sequin midi dress! The cowl sweetheart neckline and spaghetti straps add subtle chic detail, while the flattering bodycon silhouette, front slit, and midi-length hem give the right amount of sass. Complete the look in heels for a cocktail party or holiday celebration!

    Fit & Features

    • Sleeveless cowl sweetheart neckline
    • Bungee spaghetti straps
    • Bodycon silhouette, front slit
    • Midi-length hem
    • Sequin embellished fabric, knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2833

    Category Name: Midi Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Highly Selective Choker Neck Sweater Midi Dress

    Highly sophisticated and selective, this off-the-shoulder sweater midi dress is an exquisite piece for any occasion! It features a choker neckline, fitted long sleeves, and a bodycon and midi-length hem to ensure you look polished and elegant. Complete the look in booties for dinner and drinks!

    Fit & Features

    • Off-the-shoulder, choker neckline
    • Fitted long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Sweater ribbed knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1897

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • April Formal Glitter Long Sleeve Midi Dress

    Special Occasion

    The April formal glitter midi dress is a statement piece for any special occasion. Crafted from a glitter knit fabric, she features a cowl neckline, fitted long sleeves, bodycon silhouette, and a front ruched seam and slit that will flatter any figure along her midi-length hem. The formal dress is crafted from a glitter knit stretchy fabric ensuring you'll radiate sparkle all night long! Complete the look for a banquet or wedding with rhinestone heels.

    Fit & Features

    • Fitted long sleeves
    • Cowl neckline
    • Bodycon silhouette
    • Front ruched seam and slit
    • Midi-length hem
    • Glitter knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-1233

    Category Name: Midi Dresses

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Arrival Satin Ruched Midi Dress

    This satin midi dress ensures you'll make a stunning arrival at parties and dressy occasions! Crafted from luxe satin fabric, the midi-length dress features an off-the-shoulder V-neckline, short-sleeve cuffs and spaghetti straps, a form-hugging silhouette, and a front ruched seam that leads to an asymmetrical cut hem. Complete the look in rhinestone heels.

    Fit & Features

    • Off-the-shoulder V-neckline
    • Short-sleeve cuffs, spaghetti straps
    • Form-hugging silhouette
    • Front ruched seam
    • Asymmetrical midi-length hem
    • Luxe satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2725

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Greatest Hit Glitter Cowl Neck Midi Dress

    This glitter midi dress will be a hit at every party! Featuring a cowl neckline, fitted long sleeves, and side ruched seams to accentuate your curves, this bodycon dress will have all eyes on you and your sparkling glitter ensemble. Complete the look with a clutch for a birthday or banquet!

    Fit & Features

    • Fitted long sleeves
    • Cowl neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hen
    • Glitter fabric, bust knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2823

    Category Name: Midi Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Divine Celebration Satin Ruffle Midi Dress

    Be ready for every celebration in this satin midi dress for a simply divine look! Featuring a sweetheart neckline with ruffle trim, spaghetti straps that cross in the back, a bodycon silhouette, and an asymmetrical hem with a high side slit that shows off all your leg, this captivating midi-length dress is sure to turn heads. Complete the look with a ring set and heels.

    Fit & Features

    • Sleeveless sweetheart neckline, ruffle trim
    • Spaghetti straps, cross back
    • Bodycon silhouette, high side slit
    • Asymmetrical midi-length hem
    • Smooth satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2683

    Category Name: Midi Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Way You Sparkle Sequin Lace-Up Midi Dress

    Imagine the way you'll sparkle in this sequin velvet midi dress at parties or holiday banquets! The midi-length dress features a sexy plunge-wired V-neckline, a padded bust, spaghetti straps that shape the lace-up back, a flattering bodycon silhouette, and an asymmetrical hem. Complete the look with a clutch and heels!

    Fit & Features

    • Sleeveless plunge V-neckline, wire insert
    • Padded bust, back zipper and hook-eye closure
    • Spaghetti straps, lace-up back
    • Bodycon silhouette
    • Midi-length asymmetrical hem
    • Sequin velvet knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2835

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fireside Flirt Off-The-Shoulder Midi Dress

    Minimal effort, maximum slay—this knit midi dress is the definition of chic. With its off-shoulder neckline, peekaboo cutout, and side slit, it’s your new go-to for dinner dates or rooftop wine bars.

    Fit & Features

    • Stretch rib knit fabric
    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Cutout bodice
    • Front slit and button accents
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000118

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Adeline Formal Sequin Strapless Midi Dress

    Special Occasion

    Embellished with light-catching sequins, the Adeline formal midi dress deserves to shine at banquets and fancy soirees! She features a sultry strapless neckline with a wired V-notch and padded bust for structured support, a flattering bodycon silhouette, and a sassy center back slit along the midi-length hem. The formal midi dress is designed with a captivating sequin scroll embellished pattern on lightweight mesh fabric with a stretchy knit lining. Complete the look with an emerald necklace and heels!

    Fit & Features

    • Strapless wired V-notch neckline
    • Padded bust
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Center back slit, midi-length hem
    • Sequin scroll pattern, mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05001-1937

    Category Name: Midi Dresses

    Price: $29.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Robyn Formal Glitter Cutout Midi Dress

    Special Occasion

    The Robyn formal glitter midi dress is perfect for making a chic statement and sophisticated style! Beautifully appointed with a cowl neckline, spaghetti straps, and a cutout bodice, this bodycon midi dress is an elegant choice for any special occasion. The glitter-lined fabric provides a touch of luxe, and the front slit details add a flirty allure along her midi-length hem. Complete the look with earrings for a banquet or cocktail party.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps, cutout bodice
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Glitter fabric, bust knit lining, minimal stretch
    • Strapless bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1947

    Category Name: Midi Dresses

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twisted Up Long Sleeve Rib Knit Midi Dress

    Get twisted up in this stylish midi dress! The rib knit dress features fitted long sleeves, a V-neckline, a twisted bust accent, and a bodycon silhouette with flattering side ruched seams and a midi-length hem perfect for styling with your favorite booties or heels. Complete the look in best-selling shoes to make a fabulous statement this season! 

    Fit & Features

    • Fitted long sleeves
    • V-neckline
    • Twisted bust accent
    • Bodycon silhouette, side ruched seams
    • Midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5112

    Category Name: Midi Dresses

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Date Night Chic Velvet Burnout Midi Dress

    This chic velvet burnout midi dress radiates date night energy! It features a sleeveless square neckline, adjustable spaghetti straps, ruching down the side seams, a midi-length hem with a high-cut side slit for a sultry flair, and a form-hugging silhouette. The lined mesh fabric features an alluring velvet burnout floral pattern. Style this mid-length dress with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Ruched side seams
    • Midi-length hem, high-cut side slit
    • Form-hugging silhouette
    • Velvet burnout floral pattern
    • Sheer mesh fabric, full-length sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2838

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Spark Glitter Velvet Midi Dress

    Ignite a glamorous spark in this stunning glitter velvet midi dress! It features a sleeveless V-neckline with bungee spaghetti straps, an asymmetric midi-length hem creating an alluring high-cut side slit, and a bodycon silhouette to flaunt your figure. The luxe glitter velvet fabric offers a moderate stretch. Style this midi dress with metallic heels for a holiday soiree!

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Asymmetric midi-length hem, high-cut side slit
    • Bodycon silhouette
    • Glitter velvet fabric, knit lining at the bust
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2644

    Category Name: Midi Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Change Of Season Long Sleeve Ribbed Knit Midi Dress

    Step out this season in this casual-chic long sleeve midi dress! It features a V-neckline with a button design at the bust, long fitted sleeves, a midi-length hem with dual high-cut side slits, and a form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Style this midi dress with a moto jacket and ankle booties for an edgy elevated look.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline, two-button design
    • Long fitted sleeves
    • Dual side slits
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5310

    Category Name: Midi Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Fine In Floral A-Line Midi Dress

    Take your look to the next level with this gorgeous floral midi dress. With its cowl neckline, adjustable spaghetti straps, A-line silhouette, and a painted floral print on woven fabric, this midi-length dress will make you feel stylish and fine! Complete the look in sleek stiletto heels for a semi-formal soiree.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • A-line silhouette
    • Midi-length hem
    • Painted floral print
    • Lightweight woven fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2920

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love in Bloom Floral Off-Shoulder Dress

    Bloom in this lovely floral off-shoulder midi dress to enchant at every party or event! This dress hugs your curves in all the right places with soft ruching and a flared hem that moves like a dream.

    Fit & Features

    • Floral print, smooth knit stretchy fabric, lined
    • Off-shoulder neckline
    • Bodycon silhouette
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000285

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: MAUVE

    Available Size: XS, S, M