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.

  • Smooth Like Me Satin Halter Midi Dress

    No one can be smooth like you looking sultry in this satin midi dress perfect for engagement parties and semi-formal affairs! Featuring a sleeveless halter neck with spaghetti straps that lace up in the back, a bodycon silhouette, a flirty hem slit, and a front ruched drawstring so you can customize the style. Complete the look with a beaded clutch.

    Fit & Features

    • Sleeveless halter neck, spaghetti straps
    • Lace-up back
    • Bodycon silhouette
    • Front ruched, adjustable drawstring
    • Slit midi-length hem
    • Lined satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1963

    Category Name: Midi Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alia Formal High Slit Midi Dress

    Special Occasion

    The Alia formal high slit midi dress will bring those simplistic chic vibes to your look. She features a sleeveless square neckline, adjustable spaghetti straps for a customizable fit, vertical seam detailing at the bodice, a midi-length hem with a curve-hugging silhouette, and a sleek high front slit. The smooth woven fabric has minimal stretch. Style with clear heels for your next semi-formal occasion.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps, back zipper closure
    • Vertical seam detailing at the bodice
    • Midi-length hem, curve-hugging fit, high front slit
    • Woven fabric, lining at the bust, minimal stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1506

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Forever Love Rhinestone Strap Midi Dress

    You'll have a forever love for this gorgeous midi dress! It features a sleeveless V-neckline with a surplice design, rhinestone-adorned spaghetti straps for the prettiest sparkle, ruching, a curve-hugging midi-length silhouette, and a chic high-side slit. Style this dress with matching rhinestone heels for a romantic dinner date.

    Fit & Features

    • Sleeveless V-neckline, surplice design
    • Rhinestone spaghetti straps
    • Ruched detailing
    • Midi-length hem, curve-hugging silhouette
    • High side slit
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1991

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Time To Slay Bodycon Midi Dress

    It's your time to slay in this simple yet chic bodycon midi dress! It features an asymmetrical boat neckline with a partial off-the-shoulder design, long fitted sleeves with thumb hole accents, a midi-length hem, and a curve-hugging silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy heels.

    Fit & Features

    • Asymmetrical boat neckline, partial off-the-shoulder design
    • Long fitted sleeves, thumb hole accents
    • Midi-length hem
    • Curve-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5006

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dara Cutout Slit Satin Midi Formal Dress

    Special Occasion

    The Dara formal dress turns heads with its satin bodycon silhouette and statement details! A sleek cowl neckline meets a daring cutout back, while a front ruched seam and thigh-high slit bring all the drama your RSVP demands.

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining, moderate stretch
    • Cowl neckline, padded bra cups
    • Wide shoulder straps
    • Cutout back, hook strap, lower zipper and hook-eye closure
    • Front ruched seam and slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, shower celebrations, date nights, cocktail parties, dinner parties, birthdays, photoshoots, Vegas, bachelorettes

    Style Number/Barcode: 05001-000352

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: BURGUNDY, WHITE, BLACK

    Available Size: XS, S, M, L

  • The One For You Slit Midi Dress

    This one-shoulder midi dress will be essential for having in your closet for those last-minute plans! It features a sleeveless bodice, a single tank-style strap, and a front ruched seam leading to the skin-flaunting slit along the bodycon silhouette. Complete the look with hoop earrings and heels.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Single tank-style strap
    • Front ruched seam, slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2084

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bust My Luck Satin Slit Midi Dress

    You're in luck. This satin midi dress is just your style! It features a sleeveless one-shoulder neckline with an asymmetrical wide strap, a bust cutout, a form-hugging silhouette, and a sultry side slit. Complete the look in basic block heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Non-slip grip lining
    • Asymmetrical wide strap, bust cutout
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Silky satin fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1989

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirls Of Style Satin Midi Dress

    Stylish marble swirls capture all the attention on this satin midi dress featuring a sleeveless v-neck, adjustable spaghetti straps, flexible boning inserts along the bodice, and a curve-hugging silhouette with a front slit accent. Complete the look in a casual crop jacket.

    Fit & Features

    • Sleeveless v-neck, adjustable spaghetti straps
    • Flexible boning inserts
    • Back zipper and hook-eye closure
    • Front slit, curve-hugging, midi-length hem
    • Marble print
    • Satin fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4867

    Category Name: Midi Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love Me In Satin Sweetheart Dress

    Everyone will love you in this satin sweetheart dress for a luxurious look at the club! It features a sleeveless bodice, adjustable spaghetti straps, a ruched bust, flexible boning, and an asymmetrical midi-length hem with a side slit cutout. Style with a sparkly bracelet to complete the look.

    Fit & Features

    • Sleeveless sweetheart neck, ruched bust
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Flexible boning
    • Asymmetrical midi-length hem, side slit cutout
    • Lined satin, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05103-4812

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maggy Formal Satin Slit Midi Dress

    Special Occasion

    From cocktail soirees to evening art gals, the Maggy formal dress delivers sophistication to every event! She features a sleeveless sweetheart neckline, adjustable spaghetti straps, a cowl pleat overlaying the lightly padded bust, and a corset-style bodice with flexible boning. Her figure-flaunting silhouette leads to the midi-length hem with a flirty slit accent to show some skin! Complete the look with a clutch and lace-up heels.

    Fit & Features

    • Sleeveless sweetheart neckline, adjustable spaghetti straps
    • Cowl pleat overlay, lightly padded bust
    • Back zipper and hook-eye closure
    • Corset-style bodice, flexible boning
    • Form-hugging, midi-length hem with slit
    • Satin fabric, knit lining at the bust, moderate stretch
    • Bra optional
    • Runs true to size

    Style Number/Barcode: 05001-1306

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cathy Formal Crepe Slit Midi Dress

    Special Occasion

    An effortless silhouette meets its match on the Cathy formal dress you'll adore for cocktail parties and celebrations! She stuns in a captivating sleeveless, one-shoulder sweetheart neckline with a wire insert, tank-style strap, and a form-hugging midi-length silhouette with a sultry side slit. The formal dress is composed of a crepe knit fabric with a moderate stretch. Style with a sparkly bracelet and heels.

    Fit & Features

    • Sleeveless one-shoulder, sweetheart neckline
    • Wire insert, tank-style strap
    • Form-hugging silhouette
    • Midi-length hem
    • Crepe knit fabric, moderate stretch
    • Strapless or sticky bra recommended
    • Fits true to size

    Style Number/Barcode: 05001-1404

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Matilda Crepe Slit Midi Dress

    Special Occasion

    For every minimalistic-chic lover, the Matilda formal midi dress was made for you! She makes a flattering option for cocktail events, holiday parties, and dinners. Featuring a sleeveless square neckline, tank-style straps, seam detail along the bodice, and a form-hugging midi-length hem with a flirty slit. The formal midi dress is composed of a crepe fabric with a moderate stretch. Style with a sequin duster to complete your radiant look!

    Fit & Features

    • Sleeveless square neckline, tank-style straps
    • Back zipper and hook-eye closure
    • Seam detailing along the bodice
    • Form-hugging, front slit, midi-length hem
    • Crepe fabric, bust lining, moderate stretch
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1459

    Category Name: Midi Dresses

    Price: $14.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring On The Romance Floral Midi Dress

    Bring on the romance at your next dinner date in this alluring floral midi dress! It features a sleeveless cowl neckline, spaghetti straps, front ruched detailing leading to a high front slit to showcase some leg, and a midi-length hem with a curve-hugging silhouette. The lined mesh fabric features an all-over floral print pattern for a gorgeous look. Complete the outfit with strappy heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps, high waist seam
    • Front ruching, high front slit
    • Midi-length hem, curve-hugging fit
    • Floral print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1858

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve Avenue Halter V-Neck Bodycon Midi Dress

    A sleeveless midi dress designed to highlight your curves featuring a flattering halter V-neckline, bodycon silhouette, and a flirty center back slit for movement. Complete the look with earrings and booties.

    Fit & Features

    • Stretchy rib knit fabric
    • Halter V-neckline
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2220

    Category Name: Midi Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED, OLIVE, WHITE, DARK, DENIM, BEIGE

    Available Size: L, S, M

    Product Badge:
    • Sale
  • Winter Chic Style Midi Sweater Dress

    You'll adore the winter chic style of this midi sweater dress! Featuring a mock neckline, long fitted sleeves, a midi-length hem, and a form-hugging silhouette, this sweater dress is a perfect choice for casual holiday parties. The cozy brushed ribbed knit fabric offers plenty of stretch for comfortable wear. Style with ankle booties.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Midi-length hem
    • Form-hugging fit
    • Brushed ribbed knit fabric, knit lining down the body
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5039

    Category Name: Midi Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gigi Formal Glitter Slit Midi Dress

    Special Occasion

    Outshine the crowd in the Gigi formal glitter dress destined to sparkle at your upcoming holiday parties, celebrations, and date nights! She features a sleeveless cowl neckline, spaghetti straps, an open lace-up back design, a form-hugging silhouette, and a sultry front slit along the midi-length hem. The formal dress is composed of a glitter fabric with a sewn-in knit lining with plenty of stretch. Style with lucite block heels to complete the look! 

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Open lace-up back design
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Glitter fabric, sewn-in knit lining, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1221

    Category Name: Midi Dresses

    Price: $29.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Back Of My Mind Crepe Slip Dress

    You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Form-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4826

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap It Up Cable Knit Sweater Dress

    Wrap yourself up in style this season! Cue compliments whenever you're in this cable knit sweater midi dress featuring long balloon sleeves, a v-neckline, and a surplice bodice with a tie-front waist belt and a bodycon silhouette. Style with pointed-toe booties to complete the look!

    Fit & Features

    • Long balloon sleeves
    • V-neckline
    • Surplice bodice
    • Tie-front waist belt
    • Bodycon silhouette
    • Midi-length hem
    • Cable knit fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05102-4818

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ready For Cocktail Hour Satin Mesh Midi Dress

    This gorgeous satin mesh midi dress will have you ready for cocktail hour! Featuring a sleeveless sweetheart neckline with a sleek satin bust, adjustable spaghetti straps, a ruched mesh body, and a midi-length hem with a curve-hugging silhouette, this dress is so elevated and chic. The sheer mesh fabric includes a full knit lining. Complete the look with strappy stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Satin bust, padded cups
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Ruched mesh body
    • Midi-length hem, back slit accent, curve-hugging fit
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1901

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Melanie Backless Formal Midi Dress

    Special Occasion

    Sophisticated with a sultry side, the Melanie formal midi dress will have you turning heads! She features a high scoop neckline, long fitted sleeves, an alluring open back with a lower wired V-cut design, a midi-length hem with a chic back slit, and a curve-hugging silhouette. The crepe fabric offers a moderate stretch. Style with strappy stilettos for your next fancy date night.

    Fit & Features

    • High scoop neckline, long fitted sleeves
    • Open back, lower wired V-cut design
    • Midi-length hem, back slit
    • Curve-hugging fit
    • Crepe fabric, moderate stretch
    • Sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1437

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow Floral Midi Dress

    You'll love the casual vibes of this breezy floral midi dress! It features a sleeveless V-neckline with a padded bust and a draped accent, side cutouts at the waist, adjustable spaghetti straps that lead to a cross-back design, a partially open back with an elastic band, a flowy, midi-length, A-line silhouette, and a high front slit. The lightweight woven fabric features an all-over dainty floral print pattern. Style this dress with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline, padded bust, draped accent
    • Side cutouts at the waist
    • Adjustable spaghetti straps, cross-back design
    • Partially open back, elastic band, zipper, hook and eye closure
    • Flowy, midi-length, A-line silhouette, front slit
    • Floral print, woven fabric, lining at the bust, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2313

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty In Fall Cable Knit Dress

    Stay flirty and cozy this fall in this cable knit midi dress! It features long sleeves, a mock neck, a bodycon silhouette, and a sultry open-back design. Perfect for styling with faux suede booties for your weekend plans!

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Open-back design
    • Midi-length hem
    • Soft cable knit sweater fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1614

    Category Name: Midi Dresses

    Price: $18.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dreamy Energy Sleeveless Bodycon Midi Dress

    Step out looking like a dream in this sleeveless midi dress in a flattering bodycon fit perfect for dressing up.

    Fit & Features

    • Stretchy knit fabric, knit lining
    • Square neckline
    • Spaghetti straps
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3932

    Category Name: Midi Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: PINK, SAGE, HUNTER

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

  • Claire Formal One-Shoulder Velvet Midi Dress

    Special Occasion

    Step up your formal attire with a luxe velvet dress that brings sophisticated style to your special occasion! Claire features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit, and a midi-length, curve-hugging silhouette. The dress is composed of a smooth velvet fabric that offers moderate stretch. Complete the look with rhinestone chandelier earrings.

    Fit & Features

    • One-shoulder neckline
    • Wired V-neck bust
    • Fitted long sleeve
    • High side slit
    • Midi-length hem, curve-hugging fit
    • Velvet fabric, lined bust, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1288

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale