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.

  • Shine Starter Sequin Cutout Midi Dress

    If you love to shimmer this shiny sequin midi dress will be your favorite for cocktail parties or rehearsal dinners! The midi dress features a fitted long sleeve, a one-shoulder neckline, a sultry cutout waist, and a form-hugging silhouette. Complete the look in glitter block heels for extra glam!

    Fit & Features

    • Fitted long sleeve
    • One-shoulder neckline
    • Hidden side zipper and hook-eye closure
    • Cutout waist accent
    • Form-hugging, midi-length hem
    • Sequin-knit fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2318

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Budding Radiance Floral Velvet Midi Dress

    Unlock your radiance in this floral velvet midi dress for a dressy dinner party! It features a sleeveless square neck, adjustable spaghetti straps, a sexy bodycon silhouette, and a side slit. The mid-length dress is designed with a flocked velvet floral pattern on mesh fabric with a stretchy knit lining. Complete the look with earrings.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Flocked floral velvet pattern
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2555

    Category Name: Midi Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt With Confidence Strappy Back Midi Dress

    Blow kisses to all of your admirors as you pass by in this chic one-shoulder midi dress! It features a wide shoulder strap and an asymmetrical strappy back design, a bodycon silhouette, and a center back slit accent on stretchy ribbed knit fabric. Complete the look with a sleek bracelet and clutch. 

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Wide shoulder strap, asymmetrical strappy back design
    • Bodycon silhouette
    • Center back slit accent
    • Midi-length hem
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5054

    Category Name: Midi Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Standout Satin Cutout Midi Dress

    Standout in this sultry satin midi dress at an upcoming cocktail soiree or dressy celebration! The dress features a sleeveless crew halter neckline with dual button closures, a flirty bust cutout, dual waist cutouts, and a bodycon silhouette. Complete the look in rhinestone spiral heels for a dazzling effect!

    Fit & Features

    • Sleeveless crew halter neckline, dual button closures
    • Bust cutout, back zipper closure
    • Dual waist cutouts
    • Bodycon silhouette
    • Midi-length hem
    • Smooth satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2435

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Show Up And Stun Geometric Print Midi Dress

    Show up and stun for casual drinks with the girls in this trendy midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a form-hugging silhouette, and a color block geometric printed pattern to catch everyone's eye. The buttery-smooth lined knit fabric offers plenty of stretch for comfortable wear. Style with clear mules!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midi-length hem
    • Form-hugging silhouette
    • Color block geometric print
    • Smooth and stretchy knit fabric, full knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5260

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Luxe Velvet Wrap Midi Dress

    This smooth velvet midi dress will have you feeling luxe and glamorous for your next cocktail party. It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back strap design, a faux wrap-front with pleating at the waist, an asymmetric midi-length hem creating a chic high side slit to showcase some leg, and a form-hugging silhouette. The velvet fabric offers a moderate stretch. Complete your gorgeous look with a rhinestone clutch.

    Fit & Features

    • Sleeveless V-neckline, dart seam detailing
    • Spaghetti straps, cross-back strap design
    • Faux wrap-front, pleating at the waist
    • Asymmetric midi-length hem, high side slit
    • Form-hugging fit
    • Velvet fabric, front sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1938

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spiral Into Style Cutout Bodycon Midi Dress

    Spicy, sculpted, and impossible to ignore. This bodycon midi dress brings all the drama with edgy hardware and a cutout bodice that serves all night long.

    Fit & Features

    • Smooth knit stretchy fabric
    • Strapless sweetheart neckline
    • Padded bra cups, twist metal hardware trim
    • Cutout bodice and twist accent
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000226

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Perfect Illusion Glitter Bodycon Midi Dress

    Create the perfect illusion and show off a stunning hourglass shape in this curve-hugging glitter midi dress. It features a sleeveless square neckline, spaghetti straps, curved contrasting nude panels to create a gorgeous hourglass silhouette, a midi-length hem, and a bodycon fit. The textured glitter knit fabric offers plenty of stretch. Style with stiletto heels for date night.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Curved contrasting nude panels, hourglass illusion
    • Midi-length hem
    • Bodycon silhouette
    • Textured glitter knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2542

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catherine Formal Tie Strap Bandage Midi Dress

    Special Occasion

    Major curve appeal! The Catherine formal bandage dress perfects your silhouette and flatters to give you a flawless look at cocktail parties and dressy occasions! She features a classic sleeveless sweetheart neckline with an eyelash lace trim, tie shoulder straps, a padded bust and corset-style bodice, and a midi-length bodycon silhouette with a center back slit. The formal dress is composed of a tight-knit bandage knit fabric that helps to give the illusion of an hourglass figure! Complete the look in chic lace-up heels and jewelry.

    Fit & Features

    • Sleeveless sweetheart neckline, eyelash lace trim
    • Tie shoulder straps, padded bust
    • Corset-style bodice, back zipper and hook-eye closure
    • Bodycon silhouette, center back slit, midi-length hem
    • Bandage tight-knit fabric, moderate stretch
    • No bra required
    • Runs true to size

    Style Number/Barcode: 05001-1726

    Category Name: Midi Dresses

    Price: $39.97 $74.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic And Iconic Textured Knit Midi Dress

    Step out in this chic and iconic midi dress for your bridal shower or birthday party! It features a sleeveless sweetheart neckline with a structured and padded bust, adjustable spaghetti straps, a corset-designed bodice with piping details and a high waist seam, a midi-length hem with a back slit accent, and a curve-hugging fit. The lined knit fabric features an all-over horizontal textured pattern. Style with a rhinestone jewelry set and clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline, bust outline, structured and padded bust
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Corset-designed bodice, piping details, high waist seam
    • Midi-length hem, back slit
    • Curve-hugging silhouette
    • Textured knit fabric, smooth knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2403

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Favorite Moment Satin Printed Midi Dress

    Everyone's favorite moment will be when you stroll in wearing this satin midi dress to semi-formal events and cocktail parties! It features a sleeveless V-neck, adjustable spaghetti straps, a tie-back design, a sassy cutout bodice, and a flowy midi-length hem. The dress is composed of smooth satin fabric with a geometric print. Complete the look in heeled mules.

    Fit & Features

    • Sleeveless V-neck, adjustable spaghetti straps
    • Tie-back design, cutout bodice, bust lining
    • Flowy midi-length hem
    • Geometric print
    • Smooth satin fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2166

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Of-The-Moment Chic Swirl Print Midi Dress

    This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Hip-hugging fit, midi-length A-line silhouette
    • Thigh-high front slit
    • Swirl print pattern
    • Jersey knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4817

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Babe Cowl Midi Dress

    A contemporary babe like you will look effortlessly sultry in this sleeveless midi dress perfect for parties or dinner dates! The knee-length dress features a cowl neckline, sleek spaghetti straps, and a bodycon silhouette. Style with strappy heels to complete the look!

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, knit lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1964

    Category Name: Midi Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maia Formal Velvet Slit Midi Dress

    Special Occasion

    The Maia formal velvet dress is totally captivating at fancy parties and celebrations! She features a sleeveless square neckline with cowl pleating, adjustable spaghetti straps, a bodycon silhouette, a front ruched seam, and slit that shows some skin along her midi-length hem. The formal dress is composed of a flocked velvet pattern on mesh fabric with a stretchy knit lining. Complete the look with a gorgeous rhinestone bracelet and earrings.

    Fit & Features

    • Sleeveless square neckline, cowl pleating
    • Adjustable spaghetti straps
    • Back zipper and hooke-ey closure
    • Bodycon silhouette
    • Front ruched seam and slit
    • Midi-length hem
    • Flocked velvet pattern, mesh fabric stretchy knit lining
    • Sticky bra or pasties recommended

    Style Number/Barcode: 05001-1699

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Style Icon Cutout Bodycon Midi Dress

    This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.

    Fit & Features

    • Sleeveless asymmetric one-shoulder neckline
    • Tank strap
    • Asymmetric waist cutout
    • Midi-length hem
    • Bodycon silhouette
    • Stretchy ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5201

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jane Satin Lace-Up Midi Formal Dress

    Special Occasion

    Designed to linger in their memory long after the last toast, the Jane satin bodycon midi dress glides with intention—finished with a sultry slit and lace-up back that feels both refined and just a little risqué. 

    Fit & Features

    • Stretch satin fabric, knit lining
    • Sweetheart neckline, padded bra cups
    • Wide shoulder straps
    • Lace-up back, lower zipper and hook-eye closure
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, weddings, rehearsal dinners, engagement parties, date night, birthdays, black tie galas, dinner parties, cocktail soirees

    Style Number/Barcode: 05001-000223

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BROWN, NAVY

    Available Size: XS, S

  • Playful In Knit Halter Midi Sweater Dress

    Feeling playful? Turn up the charm in this sleeveless sweater midi dress perfect for family parties or baby showers! It features a halter neckline, skin-baring cutout sides and back, and a form-hugging fit on stretchy rib knit fabric with contrast trim. Complete the look in block heel mules.

    Fit & Features

    • Sleeveless halter neckline
    • Cutout sides and back
    • Form-hugging fit
    • Midi-length hem
    • Stretchy sweater rib knit fabric
    • Contrast trim
    • Runs true to size

    Style Number/Barcode: 06005-1697

    Category Name: Midi Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Weekend Date Striped Midi Sweater Dress

    This on-trend striped midi sweater dress is perfect for casual weekend dates this season! It features a strapless straight across neckline with an elasticized hem, a striped color block design down the silhouette of the dress with crochet accents in the knit fabric, a midi-length hem, and a curve-hugging fit. The ribbed knit fabric offers plenty of stretch. Style with strappy sandals.

    Fit & Features

    • Strapless straight across neckline, elasticized hem
    • Striped color block design, crochet accents
    • Midi-length hem
    • Curve-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1657

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Silky And Chic Satin Midi Slip Dress

    This silky and chic satin midi slip dress will effortlessly elevate your semi-formal style! It features a strapless straight-across neckline with a fold-over accent, an open back with an elasticized bar strap and a lower draped back design, a midi-length hem with a high front slit, and a flowy A-line silhouette. The satin woven fabric has minimal stretch. Pair with strappy stilettos for a cocktail party.

    Fit & Features

    • Strapless straight-across neckline, fold-over accent, no-slip strip
    • Open back, elasticized bar strap, lower draped back design
    • Hidden side zipper, hook and eye closure
    • Midi-length hem, high front slit
    • A-line silhouette
    • Satin woven fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2494

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Staple Tie-Front Midi Dress

    This trendy tie-front midi dress is a stylish summer staple! It features a sleeveless V-neckline, a tie-front design at the bust with a small keyhole cutout, spaghetti straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Pair with espadrille sandals for happy hour.

    Fit & Features

    • Sleeveless V-neckline
    • Tie-front design, small keyhole cutout
    • Spaghetti straps
    • Midi-length hem
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5250

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Knotty V-Neck Asymmetrical Midi Dress

    Babe, you deserve to get dressed up and this knit midi dress is ready to make your night! It features a sleeveless V-neckline, spaghetti straps, a bodycon silhouette, and a knotted twist asymmetrical wrap skirt that creates a flirty slit design. Complete the look with sleek stiletto mules.

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Bodycon silhouette
    • Knotted twist asymmetrical wrap skirt
    • Front slit design
    • Midi-length hem
    • Lined slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2415

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Julia Formal Faux Pearl Off-The-Shoulder Dress

    Special Occasion

    Can't you hear the bells ringing wearing the Julie formal dress as a stunning bride-to-be? She features a dramatically-chic off-the-shoulder neckline with a ruffled trim, side ruched seams that flaunt your curves, a form-hugging silhouette, and a midi-length hem with a flirty back slit. The midi dress is composed of an airy mesh-lined fabric with all-over faux pearl embellishments for a posh effect. Complete the look with dainty earrings and clear block heels for a seamless style!

    Fit & Features

    • Off-the-shoulder neckline, ruffled trim
    • Side ruched seams, back zipper and hook-eye closure
    • Form-hugging silhouette, midi-length hem, back slit
    • All-over faux pearl embellishments
    • Airy mesh fabric, sewn-in knit lining, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1562

    Category Name: Midi Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ever So Chic Wrap-Front Midi Dress

    Ever so chic, this smooth and sleek midi dress will create a figure-flattering silhouette. It features a sleeveless cowl neckline with pleated detailing, spaghetti straps, an alluring open back with a cross-back strap design, a midi-length hem with a faux wrap-front creating a stylish slit, and a curve-hugging silhouette. The knit fabric offers plenty of stretch. Complete the look with clear heels.

    Fit & Features

    • Sleeveless cowl neckline, pleated detailing
    • Spaghetti straps
    • Open back, cross-back strap design
    • Midi-length hem, faux wrap-front, front slit
    • Form-hugging fit
    • Knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1984

    Category Name: Midi Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer In Tie Dye Cutout Midi Dress

    Spend your summer in this tie-dye midi dress perfect for backyard dinners to sunset cocktails! It features a sleeveless V-neckline, spaghetti straps, a sexy cutout waist, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in trendy doorknocker earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Cutout waist
    • Bodycon silhouette
    • Midi-length hem
    • Tie-dye print, stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5225

    Category Name: Midi Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free