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.

  • Zosia Formal Ruffled Bodycon Dress

    Special Occasion

    Make a stylish statement with a formal bodycon dress that brings the elegance! The dress features a sleeveless V-neckline with a spaghetti strap, a cap sleeve on the left shoulder, a ruffled bodice, and a midi-length silhouette. The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete look with rhinestone heels.

    Fit & Features

    • Sleeveless V-neckline, cap sleeve
    • Spaghetti strap
    • Ruffled bodice
    • Midi-length silhouette
    • Crepe fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05001-0751

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropics Babe High Slit Midi Dress

    Hit the tropics in this gorge midi dress! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, a ruched side seam, and a midi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a floppy hat and sandals

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross at the back 
    • Tropical print 
    • Ruched side seam 
    • Midi length silhouette, high side slit
    • Smooth knit fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1799

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Passion Ruffled Midi Dress

    Show off your passion for florals with a midi dress that brings the romance! The dress features a sleeveless square neckline, spaghetti straps, a gorgeous blooming floral print, and a midi-length silhouette accented with a flirty ruffled high slit. The dress is composed of a lined crepe fabric that offers a curve-hugging silhouette with a moderate stretch. Style the look with platform wedges and a butterfly necklace.

    Shop Ivory Floral Version: Ruffled For Florals Midi Dress

    Shop Solid Color Version: Add Some Flair Ruffle Detail Midi Dress

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Cross-back strap design, front slit, ruffled hem
    • Midi-length silhouette
    • All-over floral print
    • Lined crepe fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1066

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Heartbreaker Mesh Midi Dress

    This midi dress will break some hearts and leave an unforgettable impression! The bodycon dress features a sleeveless sweetheart neckline, contrast piping, adjustable spaghetti straps, a high side slit for a sexy display of leg, and ruching throughout that enhances your natural curves. Complete the look in this mid-length dress with mules and a sleek clutch.

    Fit & Features

    • Sleeveless sweetheart neckline, contrast piping at the bodice
    • Adjustable spaghetti straps
    • Back zipper, hook-eye closure
    • High side slit
    • Ruched sheer mesh-lined fabric, moderate stretch
    • Midi-length silhouette, form-hugging fit
    • Runs true to size 

    Style Number/Barcode: 05101-1269

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simone Satin Halter Slit Midi Formal Dress

    Special Occasion

    Sculpted for the spotlight, the Simone formal dress is your RSVP-ready answer to sleek allure. Designed in luxe satin with a halter high neckline and form-hugging fit, this midi silhouette is finished with a sultry side slit built for dramatic entrances.

    Fit & Features

    • Stretch satin fabric
    • High halter neckline
    • Side slit
    • Form-hugging fit
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, cocktail soirees, date nights, anniversaries, formal celebration parties, black tie galas

    Style Number/Barcode: 05001-000355

    Category Name: Midi Dresses

    Price: $29.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunset Stunner Asymmetrical Midi Dress

    This dress will have you looking stunning as you watch the sunset on your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a beautiful tropical floral print, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Back cross-back design
    • Ruched detailing
    • Mid-length, form-hugging fit, asymmetrical hem
    • Knit fabric, moderate stretch, tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-1860

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Boho-Chic Crochet Midi Dress

    Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Mid-length, form-hugging fit
    • Sheer crochet fabric, fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-0949

    Category Name: Midi Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Stunner Ribbed Knit Midi Dress

    Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Open back, O-ring accent
    • Midi-length
    • Ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4071

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Let Beauty Bloom Floral Midi Dress

    Let your beauty bloom with a midi dress that is perf for the season! The dress features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back, a tropical floral print, ruching, and a midi-length silhouette with an asymmetrical hem. Complete look with wedges

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps 
    • Cross-back 
    • Tropical floral print 
    • Midi length silhouette 
    • Asymmetrical hem 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-0328

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flared And Flirty Off-The-Shoulder Midi Dress

    Keep it flirty with a midi dress that brings the flare! The dress features an off-the-shoulder neckline with a sweetheart bust and a midi-length silhouette with a trumpet hem. The dress is composed of a crepe fabric that offers a form-hugging fit with a moderate stretch. Complete the look with wedges.

    Fit & Features

    • Off-the-shoulder neckline
    • Sweetheart bust 
    • Midi-length silhouette
    • Trumpet hem
    • Crepe fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2389

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Laid Back Glamour Crochet Knit Midi Dress

    Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Mini side slit
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0674

    Category Name: Midi Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Knockout Knit Midi Dress

    Step up in this knockout midi dress that is all the rage! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a crew neckline, cap sleeves, and a midi-length silhouette accented with a high side slit. Elevate your look with square toe strappy mules and statement-making earrings!

    Fits & Features

    • Crew neckline
    • Cap sleeves
    • Midi length hem
    • High side slit
    • Ribbed knit fabric
    • Plenty of stretch, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-0897

    Category Name: Midi Dresses

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Chic Satin Midi Dress

    Sleek and chic, this satin midi dress will be your new go-to! It features a sleeveless cowl neckline, dual spaghetti straps that lead to a cross-back design, and a mid-length fitted silhouette with a subtle flared hem. Style this dress with clear heels and a trendy shoulder bag.

    Fit & Features

    • Sleeveless cowl neckline
    • Dual spaghetti straps
    • Cross-back design
    • Mid-length fitted silhouette
    • Satin fabric
    • Runs true to size

    Style Number/Barcode: 05101-0942

    Category Name: Midi Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Luxe Sheen Strapless Ruched Satin Midi Dress

    Show off a luxe sheen in this curve-hugging midi dress designed with smooth satin-knit fabric perfect for your next cocktail party. It features a strapless straight-across neckline, ruched side and back seams to flaunt your stunning figure, and a back slit accent at the midi-length hem.

    Fit & Features

    • Satin knit fabric, plenty of stretch
    • Strapless straight neckline
    • Ruched side and back seams
    • Back zipper closure
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3797

    Category Name: Midi Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: EMERALD

    Available Size: XS, S, M, L

  • Stylish Twist Ribbed Knit Midi Dress

    Give your midi dress a stylish twist with chic details! The dress features a sleeveless crew neckline, a twist knot accent at the back with a lower back keyhole, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless crew neckline
    • Twist knot accent at back
    • Lower back keyhole
    • Midi length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0942

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Beauty Mesh Midi Dress

    Showcase floral beauty with a midi dress that brings the charm! The dress features a sleeveless square neckline, spaghetti straps, a floral print, and a midi length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Floral print
    • Midi length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1007

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Knit Chic Cutout Midi Dress

    Keep it chic with a midi dress that brings all the appeal. The dress features a sleeveless scoop neckline, a midriff cutout, spaghetti straps, a mini-length silhouette with a midi length overlay. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges

    Fit & Features

    • Sleeveless scoop neckline
    • Midriff cutout 
    • Spaghetti straps
    • Mini length silhouette with overlay
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-0995

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sinéad Formal Asymmetrical Ruched Dress

    Special Occasion 

    Keep it sophisticated and luxe with a formal dress that elevates your formal evening. Sinéad features a one-shoulder neckline with a single spaghetti strap, a ruched body, and an asymmetrical hem with an adjustable drawstring. The dress is composed of a smooth knit fabric that provides a form-hugging fit with a moderate stretch. Complete look with heels and door knocker earrings.

    Fit & Features

    • One-shoulder neckline, single spaghetti strap
    • Strapless or adhesive bra recommended
    • Ruched body
    • Asymmetrical hem with adjustable drawstring 
    • Smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05002-1314

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Day Crochet Knit Midi Dress

    Keep it casual with a midi dress that will have you channeling your bohemian side. The dress features a sleeveless V-neckline, spaghetti straps, a tie waist belt, and a midi length silhouette, The dress is composed of a crochet knit fabric that offers a relaxed fit with a slight stretch. Complete look with wedges

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps 
    • Tie-waist belt
    • Midi length silhouette
    • Crochet knit fabric 
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0921

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry And Stunning Halter Midi Dress

    Get a sultry and stunning look for date night in this curve-hugging midi dress. It features a sleeveless halter neckline, an open back with a subtle strappy design, and a mid-length, form-fitting silhouette. The dress is composed of a slinky lurex fabric. Complete the outfit with a faux leather jacket and clear heels.

    Fit & Features

    • Sleeveless halter neckline
    • Open back, strappy design
    • Mid-length, form-hugging fit
    • Slinky lurex fabric
    • Runs true to size

    Style Number/Barcode: 05101-0996

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The One Ribbed Knit Midi Dress

    This ribbed midi dress is the one you can't live without, bby! The dress features a sleeveless square neckline, supportive tank shoulder straps, a high side slit accented with metal snap buttons, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • High side slit 
    • Snap buttons
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0955

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trend Moment Lace-Up Bodycon Midi Dress

    Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.

    Fit & Features

    • Knit fabric with moderate stretch
    • Square neckline
    • Lace-up front bust
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6072

    Category Name: Midi Dresses

    Price: $9.97

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M

  • Sleek Style Sleeveless Asymmetrical Dress

    Showcase a sleek style in this sultry sleeveless knit dress! It features a V-neckline, spaghetti straps, ruched detailing down the sides, a mid-length asymmetrical hem to show some leg, and a curve-hugging silhouette. Complete the look with trendy clear heels and a chic clutch.

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Ruching down the sides
    • Mid-length asymmetrical hem
    • Knit fabric
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-0936

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Romantic Beauty Floral Midi Dress

    Showcase your beauty on your next date night with bae in this romantic floral midi dress. It features a sleeveless square neckline, spaghetti straps, all-over ruched detailing, and a mid-length, curve-hugging silhouette. Style this dress with sleek hoop earrings and new heels for an eye-catching look.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched detailing
    • Mid-length, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 05101-1030

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free