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.

  • Sultry Sophistication Crepe Slip Midi Dress

    Slip into this sophisticated crepe midi dress for a chic date night! It features spaghetti straps, a V-neckline, and a midi-length hem with a front slit. Style with lucite heels and sparkly earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, front slit
    • Back zipper closure
    • Crepe fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1306

    Category Name: Midi Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sheila Crepe Corset Midi Formal Dress

    Special Occasion

    Romantic sparks fly in the Sheila formal dress for your next evening out! She brings classy sophistication in an off-the-shoulder drape neckline on the corset-style bodice with flexible boning to flaunt your curves. Her fitted, empire waist shapes the midi length hem with a back slit and zipper closure. The formal dress is composed of a crepe-lined fabric with a moderate stretch. Complete your look in statement earrings and satin heels.

    Fit & Features

    • Off-the-shoulder, short-sleeve cuffs
    • Corset-bodice, flexible boning, adhesive bra recommended
    • Fitted, empire waist
    • Midi hem, slit accent
    • Back zipper, hook-eye closure
    • Crepe-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05001-0861

    Category Name: Midi Dresses

    Price: $19.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pure Perfection Slinky Knit Drape Midi Dress

    This v-neck midi dress is pure perfection! it features spaghetti straps, a draped front, and an asymmetrical skirt. The slinky knit lurex-lined fabric offers a moderate stretch. Complete your look in chic lucite heels.

    Fit & Features

    • Spaghetti straps, v-neck
    • Draped front accent
    • Asymmetrical midi length skirt
    • Slinky knit lurex-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1180

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Crepe One-Shoulder Midi Party Dress

    Special Occasion

    Showcase your sophisticated style in the Summer midi party dress for every special occasion this season! She features a head-turning strappy back and a one-shoulder neckline, fitted bodice, and a high-cut slit on a midi hemline perfect for showing off some skin. The party dress is composed of a crepe knit fabric with a moderate stretch. Complete your look in radiant rhinestone heels and a matching clutch.

    Fit & Features

    • One-shoulder, strappy back
    • Fitted bodice
    • High-cut slit, midi hem
    • Crepe knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05001-0895

    Category Name: Midi Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set For Spring Halter Corset Floral Midi Dress

    Set the tone for spring dressing in this halter floral midi dress. The voluminous fit and flare silhouette embodies vintage charm with pretty modern details like a corset bodice and lace-up back design.

    Fit & Features

    • Delicate floral print
    • Poplin woven fabric, tulle and woven linings
    • Halter V-neckline with tie straps, wired underbust
    • Side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Fit and flare silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000454

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M

  • Radiate And Dazzle Glitter Velvet Dress

    Bring the dazzle with a glitter dress that shimmers from all your best angles. The dress features a sleeveless cowl neckline, spaghetti straps, and a midi-length silhouette. The dress is composed of a glitter velvet fabric that offers a form hugging fit with a moderate stretch. Complete look with glitter heels

    Fit & Features

    • Sleeveless cowl neckline 
    • Spaghetti straps
    • Midi length silhouette
    • Glitter 
    • Lined velvet fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1299

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sophisticated Collared Midi Dress

    Keep your look sleek and sophisticated in a midi dress that's a major staple! The dress features a collared neckline, long sleeves, a side slit, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a plaid coat and ankle booties. 

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Side slit
    • Midi length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4197

    Category Name: Midi Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Moment High Slit Knit Midi Dress

    Create a major style moment with a midi dress that wows! The dress features a square neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties and a cabby hat.

    Fit & Features

    • Square neckline
    • Long fitted sleeves
    • High side slit
    • Midi-length silhouette
    • Knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4287

    Category Name: Midi Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready For It Satin Midi Dress

    You'll be ready to stylishly strut in this sleek satin midi dress! It features a sleeveless one-shoulder neckline with dual spaghetti straps, ruching down the sides, and a mid-length, curve-hugging fit. The satin-knit fabric offers a moderate stretch. Complete your party look with gold hoops and clear heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Dual bungee spaghetti straps
    • Ruching down the sides
    • Mid-length, form-fitting silhouette
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1241

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Next Level Midi Dress

    Take your look to the next level with a midi dress that demands drama! The dress features a crew neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • High side slit
    • Midi-length silhouette
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4138

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Festive Cheer Velvet Slit Midi Dress

    Ring in the holiday season with this velvet slit midi dress for every party on your calendar! It features adjustable spaghetti straps, a square neckline, and a form-fitting silhouette and zipper closure. The luxe velvet offers minimal stretch. Complete your look with glitter heels and a clutch. 

    Fit & Features

    • Adjustable spaghetti straps
    • Sleeveless, square neckline
    • High-cut slit, midi-length hem
    • Form-fitting silhouette
    • Zipper closure
    • Velvet-lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1321

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Holiday Luxe Velvet Tie-Back Ruched Dress

    Make an appearance at every holiday party in this luxe velvet dress! It features a square neckline with spaghetti straps, an empire waist, a midi-length hem, an open back with a tie detail, and ruching at the lower back to accentuate your curves. Perfect for styling with sexy heels and a glitter clutch.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Empire waist, midi-length hem
    • Slit accent
    • Open-back, tie detail, ruching at the lower back
    • Luxe velvet fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1282

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Drew One-Shoulder Midi Formal Dress

    Special Occasion 

    Flaunt your gorgeous self in the jaw-dropping drew midi dress! She features a one-shoulder design with a cutout accent, knotted strap, and side ruching to highlight your curves. Her midi-length hem elongates your figure and the lined fabric offers a moderate stretch. Add the perfect finishing touch to your look with sparkly earrings.

    Fit & Features

    • One-shoulder design, cut out accent 
    • Knotted shoulder strap
    • Side ruching 
    • Bodycon silhouette
    • Midi-length hem
    • Lined fabric with moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-0867

    Category Name: Midi Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ava Cowl Neck Bodycon Mesh Lace Midi Formal Dress

    Special Occasion

    Romantic lace mesh and a bodycon fit come together to create the gorgeous Ava midi formal dress! 

    Fit & Features

    • Lace mesh lined fabric
    • Adjustable spaghetti straps
    • Cowl neckline
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, bridal showers, bachelorettes, rehearsal dinners, engagement parties, cocktail soirees

    Style Number/Barcode: 05001-000033

    Category Name: Midi Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M, L, XL

  • Holiday Chic Cowl Neck Wrap Midi Dress

    Look chic for the holidays in this sultry midi dress for every soiree! It features a sleeveless, cowl neckline, and spaghetti straps that shape the sultry open back with criss-cross detail. The form-fitting silhouette highlights your curves in a wrap-style midi skirt. Composed of a sleek knit fabric with a moderate stretch. Perfect for styling with lace-up heels.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Cowl neck, bra-friendly
    • Criss-cross back
    • Form-fitting wrap midi hem
    • Sleek knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1248

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Silhouette Marble Mesh Midi Dress

    The silhouette of this trendy mesh midi dress will hug your curves! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the sides, and a mid-length hem. The sheer mesh fabric includes a full knit lining and an eye-catching marble print. Style this dress with clear mules.

    Fit & Features

    • Sleeveless square neckline, elastic band
    • Bungee spaghetti straps
    • Ruching down the sides
    • Mid-length, form-hugging silhouette
    • Sheer mesh fabric, knit lining, moderate stretch
    • Marble print
    • Runs true to size

    Style Number/Barcode: 05102-4330

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Life Of The Party Glitter Midi Dress

    Shine like the life of the party in this mini dress that brings sparkle to your celebrations! The dress features a sleeveless V-neckline, bungee spaghetti straps, an asymmetrical high side slit for a sultry show of leg, and a midi-length silhouette. The dress is composed of a lined glitter knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a moto jacket.

    Fit & Features

    • Sleeveless V-neckline, adhesive bra recommended
    • Bungee spaghetti straps
    • Asymmetrical high side slit
    • Midi length silhouette
    • Glitter knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1249

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Chic High Slit Slip Dress

    Keep it effortlessly chic in a slip dress that stuns with ease. The dress features a sleeveless V-neck, spaghetti straps, a flirty high side slit on the slip-styled silhouette, and a midi length. The dress is composed of a lightweight woven nylon fabric that offers a relaxed fit with minimal stretch. Complete look with mules and a dainty chain necklace. 

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Bra-friendly
    • Slip-styled silhouette
    • Midi length, high side slit
    • Lightweight woven fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1310

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trista Formal Ruffled Sequin Midi Dress

    Special Occasion 

    Make a sparkling impression with the Trista formal midi dress that captures that glow just right! Trista features a sleeveless square neckline, bungee spaghetti straps, padded cups for a supportive fit, a fitted bodice leading to a mid-length silhouette with a ruffled side slit, and all-over dazzling sequin embroidery. The dress is composed of a lined mesh fabric that offers a curve-hugging fit with minimal stretch. Complete the look with rhinestone heels.

    Fit & Features

    • Sleeveless square neckline, bungee spaghetti straps
    • Padded cups
    • High side slit, ruffled trim, all-over sequin embroidery
    • High waist seam
    • Midi-length silhouette
    • Lined mesh fabric
    • Form-hugging fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05001-0870

    Category Name: Midi Dresses

    Price: $14.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Steal The Spotlight Leopard Slit Midi Dress

    Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length hem, flowy silhouette
    • Front slit
    • Leopard print
    • Crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4306

    Category Name: Midi Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ravishing Ruffles High Slit Midi Dress

    Keep it ravishing in a ruffled midi dress that brings the charm! The dress features a sleeveless square neckline, spaghetti straps that cross at the back, a high side slit with a ruffled trim, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric with a metallic sheen. Complete the look with a faux fur wrap and mules.

    Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

    Shop Crepe Midi VersionAdd Some Flair Ruffle Detail Midi Dress

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, cross-back strap design
    • High side slit, ruffles
    • Midi-length silhouette
    • Lined smooth knit fabric, metallic sheen 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1254

    Category Name: Midi Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Impression Asymmetrical Midi Dress

    Make a stunning impression in a midi dress that commands attention. The dress features a sleeveless wrap V-neckline, spaghetti straps, ruching, a high-side slit, and a midi-length silhouette. The dress is composed of a smooth knit fabric with a glamourous sheen finish. Complete look with mules.

    Fit & Features

    • Sleeveless wrap V-neckline 
    • Spaghetti straps
    • Ruching 
    • High side slit
    • Midi-length silhouette 
    • Smooth knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1329

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Smooth Talker Strapless Bodycon Midi Dress

    Show off your smooth moves in this strapless bodycon midi dress perfect for dressing up or down for any occasion!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000179

    Category Name: Midi Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIGHT, BLUE, MOCHA, BROWN

    Available Size: M, L, XS, S

    Product Badge:
    • Sale
  • Wrapped In Chic Ruched Midi Dress

    Wrap yourself in a chic midi dress that makes a stunning statement! The dress features a wrap V-neckline, long sleeves, ruching, an asymmetrical side slit, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels and a rhinestone anklet

    Fit & Features

    • Wrap V-neckline
    • Long sleeves
    • Ruching 
    • Asymmetrical side slit
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1228

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free