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.

  • The Little Things Ribbed Knit Mini Dress

    It's the little details that make your look! Stun with a mini dress that makes a major impression! The dress features a sleeveless square neckline, spaghetti straps, a mini side slit, and a mini-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
    • Spaghetti straps
    • Mini side slit
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0592

    Category Name: Midi Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Mesmerizing Beauty Floral Mini Dress

    Showcase your mesmerizing beauty in this chic floral mini dress. It features a sleeveless wrap-front V-neckline, spaghetti straps, a wrap skirt with an asymmetric hem, and a curve-hugging silhouette. Style this dress with clear heels and a sleek clutch for a summer date night.

    Fit & Features

    • Sleeveless wrap-front V-neckline
    • Spaghetti straps
    • Wrap skirt, asymmetric hem
    • Form-hugging fit
    • Floral printed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0567

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brunch-Ready Floral Midi Dress

    Style this adorable floral midi dress for weekend brunch with the girls! It features a sleeveless square neckline, spaghetti straps, a high waist, ruching, and a mid-length, curve-hugging silhouette. The knit fabric includes a knit lining and offers plenty of stretch. Complete the look with cute sunglasses and chic mules.

    Fit & Features

    • Square neckline
    • Spaghetti straps
    • High waist
    • Ruching
    • Mid-length, form-hugging fit
    • Lined knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05101-1045

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Taking the Plunge Scoop Neck Midi Dress

    Take the plunge in this stylish midi sweater dress! The dress features a sleeveless scoop neckline, tank shoulder straps, and a bodycon silhouette on rib-knit fabric. Complete the look with mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-shoulder straps
    • Bodycon silhouette
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1233

    Category Name: Midi Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dreamy Vacay Vibes Midi Dress

    Get those dreamy vacay vibes in this stunning midi dress! It features a sleeveless V neckline, adjustable spaghetti straps, an asymmetric mid-length hem with a side slit, and a curve-hugging silhouette. The knit fabric has a gorgeous all-over tropical floral print. Complete the look with strappy sandals and some cute sunnies.

    Fit & Features

    • V neckline
    • Adjustable spaghetti straps
    • Asymmetric mid-length hem
    • Side slit
    • Form-hugging fit
    • Knit fabric, floral print
    • Runs true to size

    Style Number/Barcode: 05102-0586

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Stunning Cowl Neck Midi Dress

    You'll look simply stunning in this chic midi dress that is perf for date night. It features a sleeveless bodice, spaghetti straps that lead to a cross-back design, a trendy cowl neckline, and a fitted mid-length silhouette with a sultry front slit. Complete the outfit with sparkly earrings and new heels.

    Fit & Features

    • Spaghetti straps
    • Cross-back design
    • Cowl neckline
    • Front slit
    • Mid-length, form-hugging fit
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-0999

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dinner Downtown Sleeveless Ruched Midi Dress

    The perfect chic sleeveless midi dress for grabbing dinner downtown! Crafted from smooth knit fabric, this crew neck dress boasts curve-accentuating ruched seams along the bodycon silhouette and a sleek midi-length hem. Pair with kitten heels and a clutch.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Sleeveless crew neck
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000111

    Category Name: Midi Dresses

    Price: $32.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S

  • Bold Impressions Sleeveless Midi Cutout Dress

    Make a bold impression with a midi dress that cuts a sultry look! The midi dress features a plunging V-neckline, spaghetti straps, sexy cutouts at the waist, 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 the look with mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual cutouts at the waist
    • Midi-length silhouette
    • Sheer ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1967

    Category Name: Midi Dresses

    Price: $34.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Stunner Midi Dress

    Showcase stunning looks for your next date night in this curve-hugging midi dress. It features spaghetti straps that lead to a cross-back design, a cowl neckline, a sultry side slit, and a form-fitting, mid-length silhouette. Complete the outfit with mules and a sleek clutch.

    Fit & Features

    • Spaghetti straps
    • Cross-back design
    • Cowl neckline
    • Thigh-high side slit
    • Form-hugging, mid-length silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-0946

    Category Name: Midi Dresses

    Price: $5.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Babe One-Shoulder Ruched Dress

    You'll look like such a babe in this sultry-chic sleeveless dress! It features a one-shoulder neckline with a spaghetti strap, a high waist seam, front ruching with a drawstring detail leading to a thigh-high slit, and a curve-hugging silhouette. Complete the look with hoop earrings and new heels.

    Fit & Features

    • One-shoulder neckline
    • Single spaghetti strap
    • High waist seam
    • Front ruching, drawstring detail
    • Thigh-high slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05103-3763

    Category Name: Midi Dresses

    Price: $18.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Eyes On You Asymmetrical Mini Dress

    Let this mini dress draw all eyes on you! The mini dress features a sleeveless V-neckline, a cross-back strap design, a ruched side seam to accentuate your curves, and an asymmetrical mini-length hem. The dress is composed of a stretchy satin fabric that offers a form-hugging fit. Complete the look with metallic heels for your next date night.

    Fit & Features

    • Stretchy satin fabric
    • Sleeveless V-neckline
    • Spaghetti straps, cross-back design
    • Ruched side seam 
    • Asymmetric mini-length hem 
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05101-2556

    Category Name: Midi Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Babe Sleeveless Midi Dress

    Hey babe, show off your adorable style in this floral midi dress that is perf for spring. It features a sleeveless square neckline, thin ruffle shoulder straps, a fitted bodice, and a flowy mid-length silhouette with a thigh-high slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless square neckline
    • Thin ruffle shoulder straps
    • Fitted bodice
    • Flowy mid-length silhouette
    • High front slit
    • Ditsy floral print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0741

    Category Name: Midi Dresses

    Price: $20.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Basics Ribbed Knit Midi Dress

    Bring your look back to basics with a knit midi dress that can be dressed up or dressed down for whatever mood you're in. The dress features a sleeveless V-neckline, tank-like shoulder straps, and a midi length silhouette. Complete look with clear mules

    Fit & Features

    • Sleeveless V-neckline
    • Tank-like shoulder straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0932

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Off The Shoulder Asymmetrical Midi Dress

    Keep it fab in a floral midi dress that brings the romance to your outfit! The dress features an off the shoulder neckline, off the shoulder straps, a sweetheart bust with padded cups, a built-in no-slip strip, and a floral print. The relaxed fit bodice leads to a stunning asymmetrical midi length silhouette. Complete look with wedges

    Fit & Features

    • Off the shoulder neckline 
    • Sweetheart bust, padded cups, gel no-slip strip 
    • Floral print
    • Asymmetrical midi-length silhouette
    • Lined smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0465

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ruffled For Florals Midi Dress

    Bring the charm with florals and ruffles in this sweet and stunning midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back strap design, a chic front slit with flirty ruffle detailing at the hem, and a mid-length, curve-hugging silhouette. The lined scuba knit fabric showcases a gorgeous all-over blooming floral print. Pair this pretty dress with wedges for a head-turning look!

    Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

    Shop Crepe Midi Version: Add Some Flair Ruffle Detail Midi Dress

    Shop Satin Midi Version: Ravishing Ruffles High Slit Midi Dress

    Shop Green Floral Version: Floral Passion Ruffled Midi Dress

     Fit & Features

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

    Style Number/Barcode: 05101-0513

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

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

    Special Occasion

    Made to turn heads with every step, the Mayven is your RSVP-ready answer to sleek sultriness. Designed in a bodycon silhouette with a halter square neck and lace-up back, this midi dress serves drama with a front slit made for grand entrances.

    Fit & Features

    • Sleek knit stretchy fabric
    • Square halter neckline
    • Spaghetti straps
    • Lace-up back
    • Front slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, weddings, rehearsal dinners, engagement parties, birthdays, date nights, cocktail parties, milestone celebrations

    Style Number/Barcode: 05001-000374

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS, S, M, XL

  • Sweet And Chic Ditsy Floral Midi Dress

    Keep it sweet with a stunning midi dress that brings the charm! The dress features a V-neckline, short flutter sleeves, a button-down front, a fab floral print, a tie waist belt with loops, an elastic back, and a midi-length silhouette with a ruffled hem. The dress is composed of chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges

    Fit & Features

    • V-neckline
    • Short flutter sleeves, button-down front 
    • Ditsy floral print
    • Tie waist belt with elastic back 
    • Midi length silhouette
    • Chiffon fabric, mini skirt length lining
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-0988

    Category Name: Midi Dresses

    Price: $5.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Making Stylish Moves Ruched Midi Dress

    Make a stylish move in a midi dress that draws all eyes on you! The midi dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, padded cups, a hook and eye fastening closure, a ruched body, and a midi length silhouette. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded cups, adjustable spaghetti straps
    • Hook and eye fasten closure 
    • Ruched body
    • Midi length silhouette
    • Lined mesh fabric, runs true to size 
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05101-0985

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glow On Babe Glitter Midi Dress

    Let this glitter dress bring the glow to your look to match that highlight, girl! The dress features a sleeveless scoop neckline, spaghetti straps, and a midi length silhouette. The dress is composed of a glitter knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules to create that stunning GNO outfit. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Midi length silhouette
    • Glitter knit fabric 
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05101-0671

    Category Name: Midi Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Level Up Ruched Knit Midi Dress

    Level up your basic look with this trendy ruched knit midi dress. It features a sleeveless bodice, bungee spaghetti straps, a square neckline, all-over ruched detailing, and a mid-length, curve-hugging silhouette. The soft brushed knit fabric includes a lining and offers plenty of stretch for comfortable wear. Complete your outfit with a layered necklace and sleek heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Strapless bra recommended
    • All-over ruched detailing
    • Mid-length, form-fitting style
    • Lined-knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4437

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strut It Out Ruched Cutout Midi Dress

    Create a runway moment in this stunning midi dress to style with your favorite clear mules for that upcoming birthday celebration! The dress features a sleeveless square neckline, a sexy midriff cutout with a matching lower back keyhole cutout, and a ruched body throughout. The dress is composed of a smooth knit fabric that offers a form-hugging fit with plenty of stretch.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midriff cutout, lower back keyhole cutout
    • Ruched body
    • Midi-length silhouette, form-hugging fit
    • Smooth knit fabric, full knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1960

    Category Name: Midi Dresses

    Price: $19.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leann Formal Ruched Knit Dress

    Special Occasion 

    Make a mesmerizing entrance in the captivating Leann formal ruched knit dress. The dress features a sleeveless cowl neckline, sleek spaghetti straps, and ruched side seams with drawstrings that give you the option to wear the dress as a mini, midi, or long silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with sleek rhinestone heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Sleek spaghetti straps 
    • Ruched body
    • Dual drawstrings
    • Can be worn as a mini, midi, or long silhouette
    • Smooth knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05002-1206

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Moment of Glam Cowl Neck Midi Dress

    Create a glam moment in this chic midi dress that commands attention from the moment you enter the room! The dress features a sleeveless cowl neckline, sleek spaghetti straps that lead to an x-back design, and a midi length silhouette with a high side slit. Complete look with mules

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • X-back 
    • Midi length silhouette 
    • High side slit
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05101-0954

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Vibes Ruched Floral Midi Dress

    Give your outfit major flirty vibes when you wear this adorable midi dress! It features spaghetti straps, a scoop neckline, ruched detailing, and a mid-length, curve-hugging silhouette. The brushed knit fabric showcases an all-over floral print for a beautiful look. Style this dress with a dainty layered necklace and clear heels.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Ruched detailing
    • Mid-length, form-hugging fit with a moderate stretch 
    • Brushed knit fabric
    • Floral print

    Style Number/Barcode: 05101-0972

    Category Name: Midi Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free