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.

  • Stylish Staple Ribbed Knit Bodycon Midi Dress

    A stylish staple like this bodycon midi dress needs to be in your closet. The ribbed knit fabric offers plenty of stretch, while the form-hugging fit flaunts your curves.

    Fit & Features

    • Lined ribbed knit fabric, high stretch
    • Sleeveless square neck and back design
    • Spaghetti straps
    • High side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000066

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • On The Hunt Loepard Bodycon Midi Dress

    A perfectly fierce leopard mesh midi dress for date nights and cocktail hour! This dress flatters your figure in a bodycon silhouette complete with a center back slit for effortless movement and a midi-length hem. Style the dress with heels.

    Fit & Features

    • Leopard print, mesh-lined fabric
    • Spaghetti straps, square neckline
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3979

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sunset Dinner Lace V-Neck Floral Satin Midi Dress

    A dreamy and romantic floral satin midi dress made for sunset dinners and drinks. Crafted in a figure-skimming silhouette, this sleeveless dress features a chic lace V-neckline with a tie closure and a front slit for effortless movement. Pair with stiletto mules.

    Fit & Features

    • Premium satin fabric, floral garden print
    • Lace V-neckline, tie closure
    • Front slit
    • Figure-skimming silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3457

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Made To Impress Long Sleeve Bodycon Midi Dress

    Make a lasting impression in this long sleeve midi dress that fits like a glove! Cut from a stretchy rib knit fabric, this dress is designed to flaunt your curves in a bodycon silhouette and show some skin with the cutout neckline with a chic insert. Pair with pointed-toe heels.

    Fit & Features

    • Stretchy rib knit fabric
    • Fitted long sleeves
    • Cutout neckline with insert
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2218

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cocktail Soiree Floral Velvet Midi Dress

    Strut into the cocktail soiree in this floral velvet midi dress for a decadent party look. With a flattering cowl neckline and bodycon silhouette, you'll leave an impression! Pair with heels.

    Fit & Features

    • Floral velvet pattern on mesh fabric, sewn-in knit lining
    • Cowl neckline
    • Spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3721

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Lennon Glitter Knit Off-The-Shoulder Midi Dress

    Special Occasion

    Sparkle up the party in the gorgeous Lennon formal midi dress designed with glitter knit fabric for a glam sheen that will turn heads. It features an off-the-shoulder sweetheart neckline with a ruched padded bust and short sleeve cuffs, a ruched faux wrap-front design creating a chic slit to showcase some leg, and a midi-length form-hugging silhouette.

    Fit & Features

    • Glitter knit fabric with knit lining, moderate stretch
    • Off-the-shoulder sweetheart neckline, short sleeve cuffs
    • Ruched padded bust
    • High waist seam, ruched faux wrap-front with slit
    • Midi-length form-hugging silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2527

    Category Name: Midi Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • Cece Cutout Bodycon Wrap Satin Midi Dress

    Special Occasion

    Sexy meets chic on the Cece satin midi formal dress perfect for weddings or cocktail parties. Crafted from stretch satin, this formal dress is designed with a corset-inspired bodice for a snatched appearance and a cutout back design that will turn heads! Pair with heels.

    Fit & Features

    • Stretch satin fabric, knit lining at the bodice
    • Sweetheart neckline, padded bust
    • Adjustable spaghetti straps
    • Cutout back, straps with hook and bar closures, lower back zipper with hook-eye closure
    • Bodycon wrap silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05001-2614

    Category Name: Midi Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
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  • Charming Arrival Tie-Front Slit Midi Dress

    Arrive in this charming bodycon midi dress showcasing a flirty bust tie-front and a front slit to give you effortless movement. 

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Sweetheart neckline, tie-front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6032

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vacay Escape Halter Bodycon Crochet Midi Dress

    Escape on vacay in this must-have halter crochet midi dress perfect for enjoying a sunset dinner and drinks!

    Fit & Features

    • Crochet fabric, stretchy knit lining
    • Halter neckline, tie-back
    • Front bust tie with keyhole accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6060

    Category Name: Midi Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Soul Strapless Floral Flare Midi Dress

    A floral midi dress that'll capture your sweet essence! Designed with a strapless sweetheart neckline, this dress boasts a form-hugging fit and a trendy flare hem for effortless style.

    Fit & Features

    • Ditsy floral print lined with stretchy knit
    • Strapless sweetheart neckline, padded bra cups
    • Form-hugging fit
    • Flare midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000036

    Category Name: Midi Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Cute Ease Cap Sleeve Cutout Midi Dress

    This cap sleeve midi dress is ready to elevate any casual day look to a cute level! Designed in a flattering bodycon silhouette, this dress boasts a flirty cutout back and a back slit for effortless movement. 

    Fit & Features

    • Stretchy rib knit fabric
    • Cap sleeves
    • Scoop neck
    • Cutout back
    • Center back slit
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5908

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blissful Cutie Eyelet Bodycon Midi Dress

    Enter every room like a blissful cutie in this eyelet bodycon midi dress perfect for brides-to-be or brunch! 

    Fit & Features

    • Eyelet fabric lined with stretchy knit
    • Square neckline, ruffle trim, bust tie
    • Wide shoulder straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6098

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Easily Gorgeous Strapless Cable Knit Midi Dress

    Flaunt your gorgeous curves in this chic cable knit midi dress for brunch or a casual party. The dress boasts a flattering bodycon silhouette and a center back slit for movement.

    Fit & Features

    • Cable knit design, soft stretchy knit lining
    • Strapless neckline
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5898

    Category Name: Midi Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glittering Icon V-Neck Bodycon Midi Dress

    Step out looking like an icon in this glitter midi dress for the perfect sparkle all night! With a bodycon silhouette and wrap slit hem, this dress gives you the best look yet for date nights.

    Fit & Features

    • Glitter knit fabric, moderate stretch
    • V-neckline, padded bra cups
    • Spaghetti straps
    • Bodycon silhouette
    • Wrap slit midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4102

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Shimmering Nights Cowl Neck Glitter Midi Dress

    Shimmer all night in this sleeveless glitter midi dress featuring a stunning cowl neckline and a mermaid silhouette that flatters your curves. Pair with heels and a purse.

    Fit & Features

    • Glitter knit fabric with plenty of stretch
    • Sleeveless cowl neckline
    • One tank strap, one asymmetric spaghetti strap
    • Partial open back with asymmetric spaghetti strap
    • Midi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3808

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • Sweetest Poise Button Bodycon Midi Dress

    Polished and poised, this sweet sleeveless midi dress will elevate your everyday style with chic button accents and a bodycon fit.

    Fit & Features

    • Stretchy rib knit fabric
    • Square neckline
    • Wide shoulder straps
    • Button accents, front faux pockets
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2261

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • At Midnight Bodycon Glitter Mid Dress

    They can meet you at midnight in this sparkling glitter bodycon midi dress out on the dancefloor! 

    Fit & Features

    • Glitter fabric, bust knit lining, moderate stretch
    • Square neck
    • Spaghetti straps
    • Bodycon silhouette
    • Wrap midi-length hem
    • Runs true to size
    • Extra glitter for maximum sparkle - may have some natural fallout

    Style Number/Barcode: 05101-4111

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Captivating Blooms Corset A-Line Floral Midi Dress

    Captivate with the vintage-inspired floral print on this dreamy corset A-line midi dress with the prettiest lace trim and convenient hidden side pockets to keep your hands warm!

    Fit & Features

    • Vintage-inspired floral print
    • Woven fabric, lace trim tulle lining, stretchy knit lining
    • Lace trim sweetheart neckline, bust tie
    • Lace trim wide shoulder straps
    • Flexible boning, back zipper and hook-eye closure
    • Hidden side pockets, A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3818

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Sunshine Charm Rose Floral A-Line Midi Dress

    Sunshining days call for a sundress as pretty as this rose floral midi dress boasting the prettiest details and flattering A-line silhouette that's twirl-worthy!

    Fit & Features

    • Rose floral print
    • Woven fabric, tulle lining, woven lining
    • Scrunched square neckline and shoulder straps
    • Back zipper and hook-eye closure
    • Fitted bodice
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3927

    Category Name: Midi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dream Of Me Corset Lace-Up Floral Midi Dress

    Dreamy days call for this floral midi dress that makes your cottagecore romance a reality! With a gorgeous corset bodice, lace-up back, and voluminous A-silhouette, this dress is stunning for bridal showers or garden parties.

    Fit & Features

    • Delicate floral print, woven fabric, tulle and woven linings
    • V-neckline, adjustable spaghetti straps
    • Hidden side zipper and hook-eye closure
    • Corset bodice, flexible boning, lace-up back
    • Voluminous A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3795

    Category Name: Midi Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Staple Square Neck Eyelet Midi Dress With Pockets

    A warm weather staple, this eyelet midi dress flatters your figure and offers trendy side pockets making it perfect for day dates or bridal showers!

    Fit & Features

    • Eyelet lace fabric lined with stretchy knit
    • Square neckline with bust tie
    • Adjustable shoulder straps
    • Lace-up back, side zipper and hook-eye closure
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3940

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Love's A Picnic Strapless Gingham A-Line Midi Dress

    Be loved and admired by everyone who sees you in this gingham midi dress showcasing a flattering A-line silhouette with convenient side pockets to keep your hands warm!

    Fit & Features

    • Gingham print, woven fabric, tulle and woven linings
    • Strapless neckline
    • Back zipper closure, stretch smocked panel
    • Side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3870

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Playful And Pretty Corset Lace-Up Midi Dress

    Playful and pretty, this corset midi dress has a timeless silhouette. It has a unique lace-up back, a flattering A-line fit, and convenient side pockets that warm your hands.

    Fit & Features

    • Woven poplin lined fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable shoulder straps
    • Lace-up back, side zipper and hook-eye closure
    • A-line silhouette, front slit, side pockets
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3968

    Category Name: Midi Dresses

    Price: $9.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Elegant Ruched And Ruffled Mesh Midi Dress

    Elegantly chic, this ruched mesh midi dress features a square neckline with a V-wired center, sheer long fitted sleeves, and a bodycon silhouette to showcase your curves with a tiered ruffled hem for a stylish flair. Complete your cocktail party look with stiletto heels.

    Fit & Features

    • Sheer mesh fabric with partial knit lining, plenty of stretch
    • Square neckline with V-wired center
    • Sheer long fitted sleeves
    • Ruched side and back seams
    • Midi-length tiered ruffled hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3725

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free