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.

  • Talia Cutout Sequin Short Formal Dress

    Special Occasion

    Oh-so-gorgeous, the Talia sequin formal dress was made for glamorous nights out! She features a one-shoulder neckline with dual bungee spaghetti straps, a bold waist cutout that leads from the front to the back, a short, asymmetric-cut hem, and a curve-hugging bodycon silhouette. The fabric features all-over sequin embroidery for the prettiest shine. Complete the look with rhinestone hoop earrings.

    Fit & Features

    • One-shoulder neckline, dual bungee spaghetti straps
    • Strapless or adhesive bra recommended
    • Waist cutout that leads from the front to the back
    • High waist seam, short, asymemtric-cut hem
    • Fitted bodycon silhouette
    • Sequin embroidery
    • Runs true to size

    Style Number/Barcode: 05001-1159

    Category Name: Midi Dresses

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Late Night Vibes Chain Strap Midi Dress

    You'll be ready for a late night out in this smooth and sleek mini dress. It features a sleeveless cowl neckline, chain-link shoulder straps, a high waist seam, a mid-calf-length hem, an alluring font slit to showcase some leg, and an all-over curve-hugging fit. The knit fabric offers plenty of stretch. Complete the look with a pair of strappy stilettos.

    Fit & Features

    • Sleeveless cowl neckline
    • Chain-link shoulder straps
    • High waist seam
    • Midi-length hem, high front slit
    • Form-hugging silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1908

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Killer Curves Plunge Neck Midi Dress

    Dare to show off your killer curves in this bodycon midi dress featuring long sleeves, a plunge V-neckline, and side ruched seams to create an hourglass appearance on slinky-knit fabric. Complete the look with clear strap heels. 

    Fit & Features

    • Long fitted sleeves
    • Plunge V-neckline
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2066

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good For You Sweater Maxi Dress

    Cause you like looking good for yourself! This sweater maxi dress is the perfect staple for your seasonal closet. It features long sleeves, a collared v-neckline, a form-hugging silhouette, and a flirty front cutout slit. Style with booties for an afternoon lunch.

    Fit & Features

    • Long sleeves
    • Collared v-neckline
    • Form-hugging silhouette
    • Front cutout slit
    • Maxi-length hem
    • Ribbed knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1482

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Timeless Chic Ruffled Midi Dress

    Stun in a midi dress that reveals timeless elegance at your event! The midi dress features a sleeveless square neckline, spaghetti straps, and a ruffled high side slit. The slim-fit bodice leads to a midi-length silhouette. The dress is composed of a lined crepe fabric that offers a form hugging fit with a moderate stretch. Complete look with rhinestone heels

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruffled side slit
    • Midi length silhouette
    • Lined crepe fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1385

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Look Sweater Midi Dress

    Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.

    Fit & Features

    • Sleeveless halter neck with tie closure
    • Bodycon silhouette
    • Cutout waist, front slit
    • Midi-length hem
    • Rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1416

    Category Name: Midi Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Best Of Times Scoop Neck Midi Dress

    Have the best of times with the girls in this sleek and sultry midi dress you'll love dressing up! It features a sleeveless scoop neck with spaghetti straps and a bodycon silhouette composed of double-lined slinky knit fabric. Complete the look in a chic jacket and heels.

    Fit & Features

    • Sleeveless scoop neck
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Double-lined slinky knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2100

    Category Name: Midi Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brea Satin Halter Bodycon Midi Dress

    Special Occasion

    Made to catch the light and every gaze, the Brea formal midi dress stuns with its sleek satin finish, sculpted halter neckline, and sultry open back. A curve-tracing bodycon fit and leg-baring slit seal the unforgettable vibe.

    Fit & Features

    • Stretch satin fabric, full-length knit lining
    • Sleeveless square neckline
    • Tank halter shoulder straps
    • Open back, cross-back strappy design, lower back zipper with hook-eye closure
    • Pleating, thigh-high front slit
    • Midi-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    Wedding guests, bridesmaids, cocktail parties, dressed-up dinners, and romantic date nights.

    Style Number/Barcode: 05001-000295

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: SAGE, PINK, BROWN

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

  • Outshine The Rest Satin Midi Dress

    Outshine everyone at the party in this sultry satin midi dress featuring a sleeveless sweetheart neckline with a wire insert, wide shoulder straps, princess seams along the bodice, and a form-hugging silhouette with a side slit. Complete the look with a sparkly hair accessory.

    Fit & Features

    • Sleeveless sweetheart neckline, wire insert
    • Wide shoulder straps
    • Princess seams along the bodice
    • Form-hugging silhouette
    • Midi-length, side slit
    • Smooth satin fabric, sewn-in lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1790

    Category Name: Midi Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Effortless Crepe Midi Dress

    Be the talk of the party in this effortlessly gorgeous crepe midi dress featuring a sleeveless surplice V-neckline with spaghetti straps, a bodycon silhouette, and an asymmetrical midi-length hem. Includes a smooth knit lining and offers a moderate stretch. Complete the look with eye-catching chandelier earrings.

    Fit & Features

    • Sleeveless surplice V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Crepe fabric, smooth knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1762

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Behold Me Satin Slit Midi Dress

    Every eye will be on you in this flawless satin midi dress featuring a sleek and sleeveless scoop neck, spaghetti straps, princess seams along the form-hugging silhouette, and a front-side slit accent. The smooth satin-knit fabric offers a moderate stretch Complete the look with a gorgeous clutch purse.

    Fit & Features

    • Sleeveless scoop neck, spaghetti straps
    • Princess seams
    • Form-hugging silhouette
    • Front-side slit accent
    • Midi-length hem
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1789

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Speak Chic Satin Slit Midi Dress

    This satin midi dress speaks your language for all things glamorous! It features a sleeveless square neck with spaghetti straps, pleated accents at the waist, a form-hugging silhouette, and a side slit accent. The smooth satin-knit fabric offers a moderate stretch. Complete the look in dazzling earrings.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Pleated accents at the waist
    • Form-hugging silhouette
    • Side slit accent
    • Midi-length hem
    • Satin-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1752

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Accent Chain-Trim Midi Dress

    You'll love the chic accent of this simple yet stunning midi dress. It features a sleeveless one-shoulder asymmetrical neckline, a sleek chain-link strap design, a midi-length, curve-hugging silhouette, and a double-lined knit fabric that offers plenty of stretch for comfortable wear. Style with clear heels.

    Fit & Features

    • Sleeveless one-shoulder asymmetrical neckline
    • Chain-link strap design
    • Midi-length hem
    • Fitted bodycon silhouette
    • Double-lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2013

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Coffee Date Ribbed Knit Midi Dress

    This soft ribbed knit midi dress is perfect for fall coffee dates! It features a collared V-neckline, long fitted sleeves, a partial faux button-down front, a midi-length hem with a high front slit, and a form-hugging fit. Style with knee-high boots for a chic autumn look.

    Fit & Features

    • Collared V-neckline
    • Long fitted sleeves
    • Partial faux button-down front
    • Midi-length hem, front slit
    • Fitted silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4740

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Chic Ribbed Knit Midi Dress

    Style up this casual chic ribbed knit midi dress for every day! It features a mock neckline, short sleeves, a midi-length hem, a form-hugging fit, and a high front slit. Complete the look with hoop earrings and ankle booties.

    Fit & Features

    • Mock neckline
    • Short sleeves
    • Midi-length hem
    • Fitted bodycon silhouette
    • Front slit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4739

    Category Name: Midi Dresses

    Price: $19.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple Life Crew Tank Midi Dress

    All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.

    Fit & Features

    • Sleeveless crew neckline
    • Wide tank shoulder straps
    • Midi-length hem
    • Bodycon silhouette
    • Lined ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4772

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flare For The Drama Tube Midi Dress

    Make everyone stop and admire you in this tube midi dress at weddings or dressy parties. This form-hugging midi dress stuns with a strapless neckline, flirty front slit, and a flared hem that was made for movement.

    Fit & Features

    • Sleek knit fabric, stretchy knit lining
    • Strapless tube neckline, padded bra cups
    • Form-hugging fit
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000174

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NAVY

    Available Size: L, XL

    Product Badge:
    • Sale
  • Curvaceous Views V-Neck Midi Dress

    You'll enjoy walking past every mirror in this v-neck midi dress designed to flaunt your curves! It features a sleeveless surplice v-neckline, spaghetti straps, a form-fitting silhouette, and a front-slit accent. Complete the look in sleek stiletto heels for a dressy event.

    Fit & Features

    • Sleeveless surplice v-neckline
    • Spaghetti straps
    • Form-fitting silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Fits true to size

    Style Number/Barcode: 05101-1777

    Category Name: Midi Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Everyday Ribbed Knit Midi Dress

    Effortlessly chic for every day, this ribbed knit midi dress is a must-have for fall. It features a V-neckline, a combination of front spaghetti straps and long fitted sleeves, and a midi-length, curve-hugging silhouette. Style with ankle booties for coffee dates this season.

    Fit & Features

    • V-neckline
    • Front spaghetti straps, long fitted sleeves
    • Midi-length hem
    • Fitted bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4975

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cocktail Glam Satin Midi Dress

    Look glam for cocktail hour in this smooth satin midi dress designed to give you the perfect hourglass appearance! It features a sleeveless square neck, spaghetti straps, a princess seam bodice, a high-waist seam with side pleating, and a bodycon, wrap- asymmetrical hem. Complete your dressy look in glitter heels and a clutch.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Princess seam bodice
    • High-waist seam, side pleating
    • Bodycon silhouette
    • Midi, wrap-asymmetrical hem
    • Smooth satin fabric, lined, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1621

    Category Name: Midi Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Swirl Mesh Midi Dress

    Captivate the room with your unique style! Unveil this swirl print midi dress featuring a sleeveless V-neckline with sleek spaghetti straps, a bodycon silhouette, and an asymmetrical hem with a side slit cutout. Complete the look in strappy heels for a birthday party.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Asymmetrical midi hem, side slit cutout
    • Swirl print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4823

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Sparkle Asymmetrical Midi Dress

    Showcase a chic sparkle in this fitted crepe midi dress. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a rhinestone embellished asymmetrical trim across the front, ruching, and a midi-length, form-hugging fit with an asymmetrical cut hem. Style with stilettos.

    Fit & Features

    • Sleeveless square neckline, dart seam detailing
    • Adjustable spaghetti straps
    • Back zipper closure
    • Rhinestone embellished asymmetrical trim
    • Ruching
    • Midi-length, form-fitting silhouette, asymmetrical cut hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1798

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Links Chain Strap Midi Dress

    This stylish midi dress entered the chat! It features a sleeveless V-neckline with trendy chain link shoulder straps, a bodycon silhouette, and a front slit on stretchy, double-lined ribbed knit fabric. Complete the look in clear strap heels.

    Fit & Features

    • Sleeveless V-neckline
    • Chain link shoulder straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Double-lined, rib knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4773

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Show Off The Glitz Glitter Midi Dress

    Show off the glitz and glamour in this stunning glitter knit midi dress! It features a sleeveless cowl neckline, a structured bra top peaking out with mini iridescent rhinestone embellishments, adjustable spaghetti straps, ruching down the side seams, and a midi-length hem with a curve-hugging silhouette. Style with embellished heels for all the more sparkle.

    Fit & Features

    • Sleeveless cowl neckline
    • Structured bra top, mini rhinestone embellishments
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Sheer glitter knit fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1674

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free