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.

  • Moments Like This Strapless Ruffled Midi Dress

    Take on timeless style in this strapless midi dress for enchanting moments at every soiree! The knee-length dress features a strapless neckline, a bodycon silhouette, dual front slits, and cascading ruffle trim down to the hem to create a voluminous effect. The smooth knit fabric offers plenty of stretch. Complete the look in strappy heels.

    Fit & Features

    • Strapless neckline
    • Bodycon silhouette
    • Dual front slits, cascading ruffle trim
    • Midi-length hem
    • Smooth knit fabric, top lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2853

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreaming In Marble Asymmetrical Midi Dress

    Finished with a gorgeous marble print, this midi dress will be the star of the night! The knee-length dress features a sleeveless V-neckline, adjustable spaghetti straps, a crisscross back, and a  bodycon silhouette and side ruched seam that flatters your curves, while the asymmetrical midi-length hem and high side slit show off your legs. Style the midi dress with basic stiletto heels for a sunset dinner.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Crisscross back
    • Bodycon silhouette
    • Side ruched seam, high side slit
    • Asymmetrical midi-length hem
    • Marble print, bust knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5274

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dare To Be Noticed Ruffle Slit Midi Dress

    Dare to be noticed in this effortless midi dress perfect for dressy soirees and dates! Capture the moment in this knee-length dress featuring a square neckline, adjustable spaghetti straps, a cascading front ruffle trim, a flattering bodycon silhouette, and a sultry side slit on slinky knit fabric. Complete the look in block heels and a clutch.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Cascading front ruffle trim
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2828

    Category Name: Midi Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Attract Attention Crepe Ruffle Midi Dress

    Turn heads in this stunning midi dress! Crafted with crepe fabric, the bodycon silhouette features a flattering square neckline, spaghetti straps, and playful ruffle trim atop a front slit and midi-length hem. Complete the look in stiletto heels for a dressy party or date!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruffle trim, front slit
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2829

    Category Name: Midi Dresses

    Price: $19.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Unforgettable Glitter Off The Shoulder Midi Dress

    Be unforgettable in this glitter midi dress destined to sparkle on every occasion! Featuring an off-the-shoulder neckline, short sleeve cuffs, a bodycon silhouette, a side-ruched seam, and an asymmetrical midi-length hem with slit, this glitter knit fabric will make you shine. Complete the look in statement heels for a semi-formal party or celebration.

    Fit & Features

    • Off-the-shoulder neckline
    • Short sleeve cuffs
    • Bodycon silhouette, side ruched seam
    • Asymmetrical side slit, midi-length hem
    • Glitter knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2841

    Category Name: Midi Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Velvet Allure Floral Burnout Midi Dress

    Low-key sultry, high-key unforgettable. This floral velvet burnout midi dress hugs in all the right places and is perfect for date nights, rooftop cocktails, or wherever you feel like being the vibe.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Floral velvet burnout pattern
    • Sleeveless plunge V-neckline, U-shaped metal accent, keyhole cutout
    • Spaghetti straps, open back, cross-back strappy design
    • Lower back zipper hook-eye closure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000425

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Abstract Moment Mesh Mock Neck Midi Dress

    Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!

    Fit & Features

    • Mock neck, back button closures
    • Fitted sheer long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5294

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meilani Formal Sequin Scroll Slit Midi Dress

    Special Occasion

    Radiate sexy elegance in the Meilani formal midi dress perfect for serving major looks as a wedding guest or attending a banquet dinner! She features a sweetheart neckline with a square cutout, adjustable spaghetti straps, a padded and underwire bust, a bodycon silhouette that hugs your gorgeous curves, and a flattering front slit and midi-length hem. The formal dress is designed with a sparkly sequin-scroll pattern on mesh fabric with a stretchy knit lining. Complete the look with fringe earrings and silver heels!

    Fit & Features

    • Sleeveless sweetheart neckline, square cutout
    • Adjustable spaghetti straps, padded and underwire bust
    • Back zipper and hook-eye closure
    • Bodycon silhouette, front slit, midi-length hem
    • Sequin-scroll mesh fabric, stretchy knit lining
    • No bra required
    • Runs true to size

    Style Number/Barcode: 05001-1644

    Category Name: Midi Dresses

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Draw The Line Striped Sweater Midi Dress

    Draw the line at basic and reach for this sensational striped sweater dress! It features a trendy off-the-shoulder neckline, fitted long sleeves, a flattering bodycon silhouette, and dual tie-back closures, and a cutout design. Complete the look with a chic crossbody bag for day or evening plans.

    Fit & Features

    • Off-the-shoulder neckline
    • Fitted long sleeves
    • Dual tie-back closures, cutout design
    • Bodycon silhouette
    • Midi-length hem
    • Striped pattern, stretchy sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5360

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Step Up The Romance Flocked Mesh Midi Dress

    Step up the romance for your next date night with your special someone in this chic flocked mesh midi dress that brings the allure. It features an off-the-shoulder sweetheart neckline with a dainty ruffled trim, sheer short fitted sleeves, a padded bust, a bust seam outline with ruching, ruched side and back seams, a midi-length hem with a side slit, and a bodycon silhouette to flaunt your figure. The sheer mesh fabric features a floral velvet flocked pattern and includes a nude-tone knit lining. Style with stilettos and a sleek clutch.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, sheer mesh ruffled trim
    • Sheer short fitted sleeves, padded bust, bust seam outline, ruching
    • Back zipper, hook and eye closure
    • Ruched side and back seams
    • Midi-length hem, side slit, bodycon fit
    • Sheer mesh fabric, floral velvet flocked pattern, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2559

    Category Name: Midi Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Chic Paisley Mesh Ruched Midi Dress

    Dreamy boho and chic come together on this paisley print mesh midi dress you'll love for wine nights with bae! It features a cowl neckline  adorned with a shoulder strap and bungee spaghetti strap, a flattering bodycon silhouette, and a side ruched seam atop a slit and asymmetrical hem. Complete the look with strappy heels and earrings.

    Fit & Features

    • Sleeveless cowl neckline
    • Shoulder strap, bungee spaghetti strap
    • Bodycon silhouette, side ruched seam
    • Side slit, asymmetrical midi-length hem
    • Paisley print, mesh fabric, sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2924

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Obsession Marble Print Midi Dress

    The obsession you'll have with this fabulous marble print midi dress is so real! It features a V-neckline with a twist-front design, an alluring front waist cutout to showcase some skin, long fitted sleeves, a ruched side seam that leads to a high-cut side slit, and a midi-length hem with a form-hugging silhouette. The stretchy knit fabric features a trendy marble print pattern. Style this midi dress with spiral heels!

    Fit & Features

    • V-neckline, twist-front design
    • Front waist cutout
    • Long fitted sleeves
    • Ruched side seam, high side slit
    • Midi-length hem, form-hugging fit
    • Marble print, stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5309

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Stylish Wrap-Front Midi Dress

    Simply stylish, this wrap-front midi dress is a chic choice for cocktail hour. It features a sleeveless V-neckline with a wrap-front design, spaghetti straps, pleated detailing at the waist, a wrap-front skirt with an asymmetric midi-length hem, and a slim-fit silhouette. The lined crepe fabric offers a moderate stretch. Complete your look with lace-up heels.

    Fit & Features

    • Sleeveless V-neckline, wrap-front design
    • Spaghetti straps
    • Pleating at the waist
    • Wrap-front skirt, asymmetric midi-length hem
    • Slim-fit silhouette
    • Crepe fabric, full-length knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2557

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bae Tonight Faux Leather Strapless Midi Dress

    You'll look like bae tonight in this sexy faux leather midi dress! Featuring a strapless neckline, seam detailing down the front for a contour effect, a flattering bodycon silhouette, and a center back slit along the midi-length hem. Complete the look in sleek hoop earrings and heels for a birthday or night out!

    Fit & Features

    • Strapless neckline
    • Seam detailing down the front
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Faux leather fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-5317

    Category Name: Midi Dresses

    Price: $5.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kayley Off-The-Shoulder Midi Formal Dress

    Special Occasion

    Effortless allure meets sculptural elegance on the Kayley formal midi dress, designed with a striking one-shoulder neckline and a twist-front bust that draws the eye. The sleek front slit adds just enough edge for your next RSVP-worthy moment.

    Fit & Features

    • Stretch satin fabric, smooth knit lining
    • Off-the-shoulder neckline, padded bra cups
    • Twist bust accent
    • Back zipper and hook-eye closure
    • Form-hugging fit, front slit
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, bridal showers, bachelorettes, engagement photoshoots, baby showers, birthdays, date nights, black tie events, galas

    Style Number/Barcode: 05001-000356

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: WHITE, NAVY

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

  • Timeless Crush Sleeveless Ruffle Midi Dress

    A crush that's timeless? Yourself in this sleeveless midi dress! It features a square neck, spaghetti straps, a flattering bodycon silhouette, and a high-low ruffled midi-length hem on smooth knit fabric. Complete the look with a chic crop jacket and heels for a party!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Bodycon silhouette
    • High-low ruffled midi-length hem
    • Smooth knit fabric
    • Moderat stretch
    • Runs true to size

    Style Number/Barcode: 05101-2756

    Category Name: Midi Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Muse Asymmetrical Midi Dress

    Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Midi-length, asymmetrical hem, ruching down one side
    • Form-fitting silhouette
    • Geometric multi-print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5302

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artistic Muse Abstract Strapless Midi Dress

    You'll be the artsy muse in this abstract print mesh midi dress for gallery openings or an evening downtown! It features a strapless cowl neckline, flattering side ruched seams that accentuate your curves, a bodycon silhouette, and a side slit accent. Complete the look in clear strap heels for a seamless style!

    Fit & Features

    • Strapless cowl neckline
    • Back zipper and hook-eye closure
    • Side ruched seams, side slit
    • Bodycon silhouette, midi-length hem
    • Abstract print
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5295

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swirl Fun Chain Strap Midi Dress

    Perfect for your next getaway, this swirl midi dress is a must to pack in your carry-on! It features a sleeveless square neck, half chain and adjustable spaghetti straps, a bodycon silhouette, and a flirty side slit. The dress is composed of a swirl print slinky-knit fabric with a sewn-in knit lining. Complete the look in heeled sandals.

    Fit & Features

    • Sleeveless square neck
    • Half chain, adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Swirl print
    • Slinky knit fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5301

    Category Name: Midi Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Exquisite Chic Satin Cowl Neck Slit Midi Dress

    Look exquisite in this satin midi dress to dazzle at banquets or cocktail receptions! Cut to flatter your silhouette and crafted from luxurious satin, this elegant number offers a timeless style with its sleeveless cowl neckline, spaghetti straps, side pleated seam, a flirty side slit, and midi-length hem. The silky satin-knit fabric has a moderate stretch. Complete the look in simple block heels and jewelry!

    Fit & Features

    • Sleeveless cowl neckline, spaghetti straps
    • Side pleated seam
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Silky satin-knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2443

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Annika Formal Mid-Length Bandage Dress

    Special Occasion

    Create the snatched silhouette of your dreams in the iconic Annika formal mid-length bandage dress! She features a sleeveless square neckline, spaghetti straps, a hidden back zipper closure, a midi-length hem with a chic back slit accent, and a bodycon silhouette that will hug your figure. The bandage knit fabric offers a smooth and sculpted look with plenty of stretch. Style with clear heels for your next cocktail hour.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Hidden back zipper, hook and eye closure
    • Midi-length hem, back slit
    • Bodycon silhouette, sculpted look
    • Bandage knit fabric, plenty of stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1570

    Category Name: Midi Dresses

    Price: $9.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glimmer And Glitter Bodycon Tie Back Midi Dress

    Glimmer under any light in this glitter midi dress to steal the spotlight! Featuring a sleeveless square neck, tank shoulder straps, a tie-back design, a flattering bodycon silhouette, a side ruched seam, and an asymmetrical side slit hem. Complete the look in block heels for a dressy celebration!

    Fit & Features

    • Sleeveless square neck
    • Tank shoulder straps
    • Tie-back design
    • Bodycon silhouette. side ruched seam
    • Asymmetrical side slit midi hem
    • Glitter knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2708

    Category Name: Midi Dresses

    Price: $5.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Make It Cute Sleeveless Ruched Slit Midi Dress

    For casual plans and outings, make your look cute in this sleeveless midi dress perfect for inspiring your inner fashionista! It features a square neck, spaghetti straps, a form-hugging fit, a side ruched seam that accentuates your curves, a side slit, and a midi-length hem. Complete the look with a crop jacket and heels!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps
    • Form-hugging fit
    • Side ruched seam, slit
    • Midi-length hem
    • Stretchy brushed knit soft fabric
    • Runs true to size

    Style Number/Barcode: 05102-5290

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Enchanted Moment Floral Ruffled Lace Midi Dress

    Look enchanting in this floral ruffled lace midi dress showcasing a bodycon silhouette and flirty slit for movement. Pair with heels.

    Fit & Features

    • Sheer floral lace fabric with knit lining, moderate stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Ruched front
    • Asymmetric midi-length hem with ruffled trim, front slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3696

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: SAGE

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

    Product Badge:
    • Back In Stock