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.

  • Reagan Formal Open Back Midi Dress

    Special Occasion 

    Keep your look daring and stylish with a formal midi dress that elevates your formal evening wear! Reagan features a halter neck with neckties, an open back, a slim fit bodice that leads to a midi length silhouette, and a high side slit. The dress is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels and a clutch.

    Fit & Features

    • Halter neck with neckties
    • Open back 
    • Slim fit bodice
    • Midi length silhouette
    • High side slit
    • Lined crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-0687

    Category Name: Midi Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Melissa Long Sleeve Ruched Midi Dress

    Special Occasion

    Showcase a gorgeous, figure-flattering silhouette in the chic Melissa ruched midi dress. She features a V-neckline with a wrap-front design, long fitted sleeves, ruched detailing, and a mid-length, curve-hugging fit. Complete the look with statement earrings and a sleek clutch.

    Fit & Features

    • V-neckline, wrap-front design
    • Long fitted sleeves
    • Ruching
    • Mid-length, form-fitting silhouette
    • Lined slinky knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05001-0664

    Category Name: Midi Dresses

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Henley Formal Lace-Up Midi Dress

    Special Occasion

    Lace-up in a formal dress that brings the radiance to your evening! Henley features a sleeveless square neckline, spaghetti straps, a bold lace-up back, and a midi-length silhouette accented with a high-side slit. The dress is composed of a lined crepe fabric that offers a form-flattering fit with a moderate stretch. Complete look with rhinestone heels and a sphere clutch

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • Midi length silhouette
    • High side slit
    • Lined crepe fabric 
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05001-0755

    Category Name: Midi Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Stylish Affair Ruffled Midi Dress

    Make a dramatic entrance with a midi dress that is perfect for your cocktail event. The dress features a ruffled off-the-shoulder neckline a bodycon fit, and a midi length silhouette with a ruffled hem. The dress is composed of a crepe fabric that offers a form hugging fit with a moderate stretch. Complete look with stiletto heels and statement earrings.

    Fit & Features

    • Ruffled off the shoulder neckline
    • Bodycon fit
    • Midi length silhouette 
    • Ruffled hem 
    • Crepe fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-0989

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Twist Of Fate Wrap Midi Dress

    Wrap yourself in a midi dress that keeps it casually chic! The dress features a V-neckline, short kimono sleeves, a high center slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and hoops. 

    Fit & Features

    • V-neckline
    • Short kimono sleeves
    • High center slit 
    • Midi length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0990

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Trendsetter Lace Up Midi Dress

    Stun like the true trendsetter you are with a midi dress that slays! The dress features a halter neckline with a racer bust, spaghetti straps, sexy cutouts at the waist, a lace-up back, and a midi-length silhouette. The dress is composed of a buttery lined knit fabric that offers a form hugging fit with a moderate stretch.  Complete look with mules

    Fit & Features

    • Halter neckline, racer bust
    • Spaghetti straps
    • Lace-up straps at the back
    • Cutouts at the waist
    • Midi length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1096

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutout Crush Hour Midi Dress

    Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!

    Fit & Features

    • Sweater knit stretchy fabric
    • V-neckline with tie bust design
    • Adjustable spaghetti straps
    • Underbust cutout accent
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000014

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Endless Summer Halter Cutout Dress

    Embrace the summer vibes in this chic curve-hugging dress! It features a sleeveless halter neckline, an open back, a center knot detail with dual waist cutouts, and an ankle-length, form-fitting silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless halter neckline
    • Open back
    • Center knot detail
    • Dual waist cutouts
    • Long, form-hugging fit
    • Ribbed sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1216

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Romantic Vibes Floral Mesh Midi Dress

    Hey babe, bring the romantic vibes to your next dinner date in this floral mesh midi dress! It features a sleeveless cowl neckline, bungee spaghetti straps, and a mid-length, curve-hugging silhouette. The sheer mesh fabric has a pretty all-over floral print with a full knit lining. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Bungee spaghetti straps
    • Mid-length, form-hugging fit
    • Sheer mesh fabric, knit lining, floral print
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1094

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daring Diva Open Back Midi Dress

    Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings

    Fit & Features

    • Sleeveless scoop neckline 
    • Adjustable spaghetti straps, cross at back
    • Open back 
    • Midi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1210

    Category Name: Midi Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Total Showstopper One Shoulder Bodycon

    Step out like the total showstopper you are with a sexy bodycon! The bodycon features a one-shoulder neckline, a cutout at the bodice, a fitted long sleeve, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with stilettos and door knocker earrings. 

    Fit & Features

    • One-shoulder neckline
    • Cutout at bodice
    • Fitted long sleeve
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1079

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Alessandra Formal One-Shoulder Midi Dress

    Special Occasion

    Make an elegant entrance in the Alessandra formal midi dress that captivates from the moment you enter the room. She features a sleeveless one-shoulder neckline with a single tank shoulder strap, front ruched detailing, and a fitted midi-length silhouette with a chic back slit. The dress is composed of a lined crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and an anklet.

    Fit & Features

    • One-shoulder neckline, tank shoulder strap
    • Sleeveless bodice, adhesive bra recommended
    • Front ruching
    • Back slit
    • Midi-length, slim-fit silhouette
    • Lined techno crepe fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05001-0697

    Category Name: Midi Dresses

    Price: $28.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Stunner Cutout Midi Dress

    Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Halter neck, V-neck bust
    • Cutout at the midriff with straps
    • Midi length silhouette
    • High side slit
    • Lurex knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4157

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Factor Ruched Midi Dress

    This midi dress brings the chic factor to your night out look! The dress features a sleeveless sweetheart neckline, spaghetti straps, a ruched body, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels and gold hoops. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Ruched body
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05103-4118

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Chic Slinky Knit Midi Dress

    Stylish and chic, this slinky knit midi dress is a must-have for a night out with the girls. It features a sleeveless cowl neckline, spaghetti straps that lead to an open back with a strappy caged design, and a mid-length, form-fitting silhouette that will hug your curves. Complete the look with clear heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Open back, strappy caged design
    • Mid-length, form-hugging fit
    • Slinky knit fabric
    • Runs true to size

    Style Number/Barcode: 05101-1048

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kiss and Tell Sweetheart Cutout Midi Dress

    She’s sweet but knows how to steal the spotlight. This bodycon midi dress brings the heat with a front twist, flirty cutout, and high side slit that does the most (in the best way).

    Fit & Features

    • Rib knit fabric, sewn-in mesh lining, moderate stretch
    • Sweetheart neckline, cutout accent
    • Spaghetti straps
    • High side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000208

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S, M, L

  • Sweet And Sultry Vibes Mesh Midi Dress

    Bring the sweet and sultry vibes to your night-out look in this stunning mesh midi dress. It features an off-the-shoulder sweetheart neckline with a ruffled trim, short sleeves, padded cups, ruched detailing, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with hoop earrings and clear heels.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, ruffled trim
    • Short sleeves, padded cups
    • Back zipper and hook and eye closure
    • Ruched detailing
    • Mid-length, form-hugging fit, side slit
    • Sheer mesh fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1661

    Category Name: Midi Dresses

    Price: $20.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keely Lace Sweetheart Midi Dress

    Special Occasion

    The Keely lace midi dress will bring elegance to your look while also giving you subtle sultry vibes! She features a sheer lace top with a boat neckline and a scalloped trim, long fitted sheer sleeves, and a sheer open back. She has a chic tie-front ribbon belt and a curve-hugging, mid-length silhouette. The sheer lace fabric has a lining with a sweetheart neckline. Complete the outfit with rhinestone earrings and strappy heels.

    Fit & Features

    • Sheer lace top, boat neckline, scalloped trim
    • Long fitted sheer sleeves
    • Sheer open back
    • Tie-front ribbon belt
    • Mid-length, form-hugging fit
    • Sheer lace fabric, lining with sweetheart neckline
    • Runs true to size

    Style Number/Barcode: 05001-0778

    Category Name: Midi Dresses

    Price: $29.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Penelope Off-The-Shoulder Ruched Midi Dress

    Special Occasion

    Classic and chic, the Penelope midi dress is perf for your next cocktail party. She features an off-the-shoulder V-neckline with a wrap-front design, long fitted sleeves, side ruched detailing, and a mid-length, form-fitting silhouette to hug your curves. Style this dress with glitzy rhinestone earrings and strappy heels.

    Fit & Features

    • Off-the-shoulder V-neckline
    • Wrap-front design
    • Long fitted sleeves
    • Side ruching
    • Mid-length, form-hugging fit
    • Slinky knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05001-0663

    Category Name: Midi Dresses

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Lover Ruched Midi Dress

    Show off your love for florals with this midi dress that will have you totally lovestruck! The dress features a sleeveless square neckline, spaghetti straps, a floral print, a ruched body, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and hoops. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Floral print
    • Ruched body
    • Midi length silhouette
    • Smooth knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1034

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Sunsets Asymmetrical Midi Dress

    Take in those tropical vibes with a midi dress that will have you vacay-ready! The dress features a tropical palm leaf print, a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and an asymmetrical hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and sandals

    Fit & Features

    • Tropical palm leaf print
    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Midi length silhouette
    • Asymmetrical hem 
    • Smooth knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4111

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Floral Asymmetrical Midi Dress

    Get a gorgeous and dreamy look in this chic floral midi dress. It features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back design, ruched detailing, and a mid-length, curve-hugging silhouette with a high-cut asymmetrical hem. Style this dress with cute wedges.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Open back, cross-back design
    • Ruching
    • Mid-length, form-hugging fit
    • High-cut asymmetrical hem
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-1113

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Luxe Level Sleeveless Midi Dress

    Take your look to a luxe level with a stunning midi dress that creates a head-turning moment! The dress features a sleeveless cowl neckline, spaghetti straps, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Midi-length silhouette
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1120

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summertime Beauty Cutout Midi Dress

    Hey beauty! Get a gorgeous look perf for summertime in this stunning midi dress. It features a sleeveless halter neckline, dual waist cutouts, and a mid-length, form-fitting silhouette to hug your curves. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Dual waist cutouts
    • Mid-length, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4255

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale