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.

  • Roaring 20s Sleeveless Fringe Midi Dress

    Enter into the roaring 20s-inspired style wearing this sleeveless midi dress for your next cocktail party! Featuring a scoop neck, tank straps, a bodycon silhouette, and an asymmetrical hem with a fringe hem on stretchy knit fabric. Pair with clear block heels for a seamless-chic look! 

    Fit & Features

    • Sleeveless scoop neck
    • Tank straps
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Fringe trim 
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2360

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lucinda Formal Sequin Feather Midi Dress

    Special Occasion

    Simply pretty and elegant. The Lucinda sequin formal dress sparkles for brides-to-be, birthday girls, or graduates! She features a sleeveless scoop neckline, adjustable spaghetti straps for a customizable fit, a form-hugging silhouette, and a feathered midi hem with a back-slit accent. The formal dress is composed of a sequin-embroidered mesh fabric with a stretchy knit lining. Style with earrings, a bracelet, and heels to complete the look!

    Fit & Features

    • Sleeveless scoop neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Feather midi hem, back slit accent
    • Sequin-embroidered mesh fabric, stretchy knit lining
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1432

    Category Name: Midi Dresses

    Price: $29.97 $68.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Revel In Crepe Surplice Midi Dress

    You'll be reveling at yourself all evening in this crepe midi dress designed to flaunt your sultriness! It features a sleeveless V-neckline, spaghetti straps, a surplice bust, and a bodycon silhouette that leads to the asymmetrical side slit. Complete the look in strappy rhinestone heels for a wedding shower or rehearsal dinner!

    Fit & Features

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

    Style Number/Barcode: 05101-2339

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Affair High Slit Satin Midi Dress

    Make your next cocktail party a chic affair with this sleek satin midi dress. It features a sleeveless square neckline, spaghetti straps, an alluring open back with a bar strap accent, a lower back ruched knot detail, a midi-length hem with a high front slit, and a form-hugging silhouette. The satin-knit fabric offers a moderate stretch. Complete your look with rhinestone heels.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Open back, horizontal bar strap
    • Lower back ruched knot detail
    • Midi-length hem, high front slit
    • Form-hugging fit
    • Satin-knit fabric, lined bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2095

    Category Name: Midi Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty Deets Crepe Lace-Up Midi Dress

    This crepe midi dress has the pretty deets you're looking for! The dress features a sleeveless square neck, spaghetti straps, an open lace-up back with tie closure, a ruched bust, and a bodycon silhouette. Complete the look in chic flat sandals.

    Fit & Features

    • Sleeveless square neck, spaghetti straps
    • Open lace-up back, tie closure
    • Ruched bust
    • Bodycon silhouette
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4891

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Confidence Lace-Up Ruched Midi Dress

    This midi dress is for candlelit dinners and slow-motion exits. Let the ruching and lace-up back do the flirting while the ruched bodycon silhouette flaunts your curves!

    Fit & Features

    • Coated metallic slinky knit fabric, sewn-in knit lining
    • Cowl sweetheart neckline, padded bra cups
    • Spaghetti straps
    • Lace-up back
    • Ruched seams, bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000362

    Category Name: Midi Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

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

    Product Badge:
    • Sale
  • Ready To Sparkle Glitter Midi Dress

    Invited to a cocktail soiree? Get ready to sparkle in this glitter midi dress featuring a one-shoulder neckline, a peasant long sleeve, a side ruched seam, a bodycon silhouette, a sultry side cutout, and an asymmetrical hem with a cutout slit. Complete the look with chandelier earrings.

    Fit & Features

    • One-shoulder neckline, peasant long sleeve
    • Side ruched seam, cutout slit
    • Bodycon silhouette
    • Asymmetrical midi-length hem
    • Glitter knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2257

    Category Name: Midi Dresses

    Price: $5.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sparkling Glitter Lace-Up Midi Dress

    Keep it sparkling at cocktail parties and birthdays in this glitter midi dress designed to shine! It features a sleeveless square neck, spaghetti straps that lace up along the open back, a bodycon silhouette, and a side pleated seam that shapes the asymmetrical slit hem. Complete the look in clear strap platform heels for a seamlessly-chic style!

    Fit & Features

    • Sleeveless square neck
    • Spaghetti straps, lace up open back
    • Bodycon silhouette
    • Side pleated seam
    • Asymmetrical slit midi hem
    • Lined glitter fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2259

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glitter Queen Ruched Midi Dress

    You'll be a total glitter queen in this glitzy ruched midi dress made to make you sparkle. It features a sleeveless cowl neckline, spaghetti straps, front ruched detailing leading to a thigh-high slit, a midi-length hem, and a curve-hugging silhouette. The textured glitter knit fabric offers a moderate stretch. Style with clear heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Front ruching, high slit
    • Midi-length hem
    • Form-fitting silhouette
    • Textured glitter knit fabric, lined bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2718

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • First Class Cowl Neck Midi Dress

    This midi dress will put you in the first class of style! It features a sleeveless cowl neckline, a tank-style strap, and spaghetti strap, a form-hugging silhouette, and a side ruched seam atop the sultry side slit. Complete the look with earrings and a clutch.

    Fit & Features

    • Sleeveless cowl neckline
    • Tank-style strap, spaghetti strap
    • Form-hugging silhouette
    • Side ruched seam, side slit
    • Midi-length hem
    • Stretchy smooth knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2171

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Pretty Chiffon Midi Dress

    Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.

    Fit & Features

    • Sweetheart neckline, ruched bodice
    • Long sheer peasant sleeves, elastic cinched hems
    • Stretchy smocked back design
    • Fitted high waist seam
    • Midi-length hem, high front slit, A-line silhouette
    • Sheer chiffon fabric, partial knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4954

    Category Name: Midi Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Curve Illusion V-Neck Midi Dress

    Flaunt your curves in this hourglass illusion midi dress to make his jaw drop on date night! It features a sleeveless V-neck, dual spaghetti straps that cross in the back, side mesh colored panels, and a bodycon silhouette. Complete the look in stiletto heels and a clutch!

    Fit & Features

    • Sleeveless V-neck
    • Dual spaghetti straps, cross-back design
    • Side mesh colored panels
    • Bodycon silhouette
    • Midi-length hem
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-2276

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhea Formal One Shoulder Midi Dress

    Special Occasion

     Showcase your sophisticated demeanor in the Rhea formal dress to bring effortless beauty to dinner parties, mixers, and date nights! She features a sleeveless one-shoulder neckline, dual asymmetrical spaghetti straps, a form-hugging silhouette, and a flirty slit along her midi-length hem. The formal dress is composed of a crepe knit fabric with a moderate stretch. Style with sparkly hoop earrings and heels to complete the look!

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Dual asymmetrical spaghetti straps
    • Form-hugging silhouette
    • Slit accent
    • Midi-length hem
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05001-1351

    Category Name: Midi Dresses

    Price: $29.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Framed In Floral Satin Midi Dress

    You'll look pretty as a picture in this floral satin midi dress for all of your springtime frolics! It features a sleeveless v-neck, adjustable spaghetti straps a cowl pleated neck overlay, and a form-hugging silhouette with a sultry side slit. Style with a chic handbag for a date or wedding shower!

    Fit & Features

    • Sleeveless v-neck
    • Adjustable spaghetti straps
    • Cowl pleated neck overlay
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Floral print, lined silky satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2175

    Category Name: Midi Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Greta Strapless Bodycon Midi Formal Dress

    Special Occasion

    Sleek and sultry, the Greta strapless midi formal dress is tailored with ruching that sculpts the silhouette and a thigh-high slit for just the right amount of drama. The perfect blend of sophistication and allure, it’s made for evenings that leave a lasting impression.

    Fit & Features

    • Smooth knit stretch fabric
    • Strapless neckline
    • Bodycon silhouette
    • Wrap front slit
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, cocktail soirees, charity auctions, dressed-up date nights, birthdays, milestone celebrations, holidays

    Style Number/Barcode: 05001-000274

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S

  • Own Your Shine Rhinestone Strap Midi Dress

    Own your shine girl! Capture the attention in this metallic midi dress featuring a sleeveless cowl neck, rhinestone straps, and a bodycon silhouette. Style with strappy rhinestone heels to complete the look for birthdays or cocktail parties!

    Fit & Features

    • Sleeveless cowl neck
    • Rhinestone straps
    • Bodycon silhouette
    • Midi-length hem
    • Metallic knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2246

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Stroll Ditsy Floral Midi Dress

    Take a springtime stroll in this adorable ditsy floral midi dress! Featuring a square neckline, short puff sleeves, a midi-length hem with a front slit, and a flowy A-line silhouette, this dress is perfect for weekend plans. The ditsy floral printed woven fabric includes a short knit lining. Style with sandals for a date with your special someone.

    Fit & Features

    • Square neckline
    • Short puff sleeves, elastic cinched hems
    • Smocked back panel, hidden side zipper
    • Midi-length hem, front slit, A-line silhouette
    • Ditsy floral print
    • Woven fabric, short knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1985

    Category Name: Midi Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cara Formal Sequin Lace-Up Midi Dress

    Special Occasion

    Why blend in when you can shine? Glistening sequins cover the Cara formal dress ready to strike a pose at school dances or celebrations! She brings the sultry appeal in a sleeveless plunge V-neckline with a V-wire insert, lightly padded bust, spaghetti straps, and a lace-up back with tie closure. Her form-hugging silhouette leads to the skin-flaunting side slit along the midi-length hem. The formal dress is composed of a sequin scroll patterned mesh fabric with a knit lining and moderate stretch. Style with a clutch and heels to complete the look! 

    Fit & Features

    • Sleeveless plunge V-neckline, V-wire insert
    • Lightly padded bust, spaghetti straps
    • Lace-up back, tie closure, zipper and hook-eye closure
    • Form-hugging silhouette, side slit, midi-length hem
    • Sequin scroll pattern, mesh fabric, knit lining, moderate stretch
    • Bra optional
    • Runs true to size

    Style Number/Barcode: 05001-1283

    Category Name: Midi Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sofia Formal Satin Feather Midi Dress

    Special Occasion

    Forever timeless and classic, the Sofia formal satin dress embodies the 90s chic style perfect for date nights, dances, or cocktail soirees! She features a sleek and sleeveless square neck, adjustable spaghetti straps for a customizable fit, and a form-hugging silhouette with a back slit accent and feather trim midi hem. The formal dress is composed of a lustrious satin-lined fabric with a moderate stretch. Style with stiletto mules and a clutch to complete the look!

    Fit & Features

    • Sleeveless square neck, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Back slit accent, feather trim midi hem
    • Lined satin fabric, moderate stretch
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1277

    Category Name: Midi Dresses

    Price: $14.97 $84.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luisa Rhinestone V-Neck Midi Dress

    Special Occasion

    Fancy yourself as a radiant beauty in the stunning Luisa party dress? Every jaw will drop when you step into the formal dance or celebration in this sparkling midi dress featuring a sleeveless V-neckline with a sheer mesh insert, rhinestone embellished and adjustable spaghetti straps, and a bodycon silhouette. The party dress is composed of a partially lined mesh fabric with all-over rhinestone and faux pearl embellishments in a clustered vertical design to accentuate your curves! Style with fringe earrings and clear block heels to complete the look.

    Fit & Features

    • Sleeveless V-neckline, sheer mesh insert
    • Rhinestone embellished, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon silhouette, midi-length hem
    • All-over rhinestone and faux pearl embellishments
    • Partially lined mesh fabric, stretchy knit lining
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05001-1420

    Category Name: Midi Dresses

    Price: $69.97 $149.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Looking Fancy Satin Midi Dress

    Looking for something fancy? Get wine and dined in this satin midi dress featuring a sleeveless surplice v-neckline, spaghetti straps, bodycon silhouette, and a side pleated seam leading to the asymmetrical slit hem. Complete the look with a chic clutch.

    Fit & Features

    • Sleeveless surplice v-neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Side pleated seam
    • Asymmetrical slit midi hem
    • Satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2327

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Harmony Chiffon Midi Dress

    Your sweet style personality goes in harmony with this chiffon midi dress perfect for any upcoming weddings and parties! The knee-length dress features short puff sleeves, a sweetheart neckline, princess seams, and a front flirty slit along the A-line silhouette. Pair with a chic ring set and heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neck
    • Princess seams, front slit, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Airy chiffon fabric, knit lining, no stretch
    • Fits true to size

    Style Number/Barcode: 05101-1850

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Maggie Satin Bodycon Formal Dress

    Special Occasion

    Slip into the Maggie satin formal dress and let the spotlight find you—its bodycon silhouette and softly draped cowl neckline are made for captivating entrances, while the side slit gives effortless allure.

    Fit & Features

    • Stretch satin fabric, stretchy knit lining
    • Cowl neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, weddings, rehearsal dinners, engagement parties and photoshoots, black tie galas, bachelorettes, bridal showers, Vegas weekends, birthdays, formal celebrations

    Style Number/Barcode: 05001-000289

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BLACK, ROYAL, WHITE

    Available Size: XS, S, M, L

  • Ruby Formal Sequin Lace-Up Midi Dress

    Special Occasion

     Light-catching sequins shape the Ruby formal dress to bring sparkle to dinner banquets and engagement parties! She features a sleeveless plunge sweetheart neck with a v-wire insert, spaghetti straps, a lace-up back design, a bodycon fit, and a flirty slit along her midi-length hem. The formal dress is composed of a sequin scroll mesh fabric with a knit lining and minimal stretch. Style with teardrop earrings and heels to complete the look!

    Fit & Features

    • Sleeveless plunge sweetheart neck, v-wire insert
    • Spaghetti straps, back zipper and hook-eye closure
    • Lace-up back design
    • Bodycon fit, front slit, midi-length hem
    • Sequin scroll mesh fabric, knit lining, minimal stretch
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05001-1284

    Category Name: Midi Dresses

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance