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.

  • May Blooms Lace-Up Midi Dress

    May flowers are blooming on this sultry midi dress featuring a sleeveless, cowl neck, spaghetti straps that lace up on the open back, a form-hugging fit, and a side slit accent. Complete the look in simple block heels for a daytime event.

    Fit & Features

    • Sleeveless, cowl neck, spaghetti straps
    • Open-back, lace-up design
    • Form-hugging fit
    • Side slit accent
    • Midi-length hem
    • Slinky knit fabric, moderate stretch. fits true to size

    Style Number/Barcode: 05101-1625

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Heartbreaker Hourglass Midi Dress

    Soft, sleek, and serving curves. This bodycon midi dress is your go-to when you want to keep it simple but still shut it down—with flattering bust detail and a bodycon fit perfect for showing off on date night or a chic party.

    Fit & Features

    • Soft modal fabric, smooth knit lining, moderate stretch
    • Sweetheart neckline, bust detail
    • Spaghetti straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000064

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

  • Floral Finds V-Neck Midi Dress

    Lucky you! This floral midi dress was meant to be in your closet. It features a sleeveless, v-neck, sleek spaghetti straps, and a form-fitting silhouette with a ruched side seam and asymmetrical hem. Complete the look with a rhinestone fringe clutch for a dressy party.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Form-fitting silhouette
    • Side ruched seam
    • Asymmetrical midi hem
    • Floral print
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1517

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Tide Halter Cutout Midi Dress

    Flaunt this midi dress on your island getaway! Designed to accentuate your fab figure on a sleeveless, halter neck with tie closure, and sultry side cutouts on the form-fitting silhouette. Complete the look in strappy mules for a sunset dinner.

    Fit & Features

    • Sleeveless, halter neck, tie closure
    • Side cutouts
    • Partial open-back design
    • Form-fitting silhouette
    • Midi-length hem
    • Sweater-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1313

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Vacay Views Floral Midi Dress

    Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.

    Fit & Features

    • Sleeveless bodice, wrap-front V-neckline
    • Spaghetti straps
    • Fitted midi-length silhouette, asymmetrical hem
    • Form-hugging fit
    • Tropical floral print
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4441

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Perfect For Paradise Midi Dress

    This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length asymmetrical hem
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4474

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Just The Deets Lace-Up Midi Dress

    Here's the scoop, this midi dress has some sultry detail on the back! Featuring a sleeveless, square neck, spaghetti straps, bodycon silhouette, a side cutout slit, and an open-back with lace-up closure. Complete the look in saucy heels for a night out. 

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Bodycon silhouette
    • Side cutout slit
    • Open-back, lace-up closure
    • Midi-length hem
    • Sleek knit-lined fabric. moderate stretch
    • Fits true to size

    Style Number/Barcode: 05103-4371

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Daze Halter Sweater Dress

    Bring the summer vibes with this bright and trendy halter sweater dress. It features a sleeveless scoop neckline, halter spaghetti straps, an open back with a tie-back design, and a midi-length, curve-hugging silhouette. The lightweight sweater knit fabric showcases an all-over multi-hued chevron pattern. Complete the look with espadrille sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Halter spaghetti straps, tie at the back of the neck
    • Open back, tie-back strap design
    • Midi-length, form-fitting silhouette, scalloped hem
    • Multi-hued chevron pattern
    • Unlined sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1312

    Category Name: Midi Dresses

    Price: $12.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jetset Getaway Tropical Midi Dress

    Wanna get away? Jetset off to paradise with this tropical floral dress in your lineup! It features a sleeveless scoop neck, spaghetti straps, a cross-back strap design with a tie closure, a form-fitting silhouette, a side ruched seam, and an asymmetrical midi hem with a side slit. Complete the look in lace-up heels.

    Fit & Features

    • Sleeveless, scoop neck, spaghetti straps
    • Open-back, cross-back strap design, tie closure
    • Form-fitting silhouette
    • Side ruched seam
    • Asymmetrical midi-length hem, side slit
    • Tropical floral print, stretchy knit-lined fabric
    • Runs true to size

    Style Number/Barcode: 05102-4373

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Cruise Floral Midi Dress

    You'll be ready for a sunset cruise on the water in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, side ruched detailing, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some leg. The dress features an all-over tropical floral print. Complete the look with strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-back strap design
    • Side ruching
    • Midi-length, form-fitting silhouette, asymmetrical hem
    • Tropical floral print
    • Stretchy knit fabric, partial lining at the bust
    • Runs true to size

    Style Number/Barcode: 05102-4375

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tori Lace-Up Satin Midi Formal Dress

    Special Occasion

    The Tori satin formal dress redefines effortless elegance for your most special events! This sultry satin midi dress hugs just right with a head turning lace-up back and a front slit that knows how to work a room. 

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining
    • V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Lace-up back, lower zipper and hook-eye closure
    • Front wrap slit
    • Form-hugging fit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, fancy celebrations, date nights, formal events

    Style Number/Barcode: 05001-000221

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, S, M

  • Gracelyn Crepe Cross Midi Dress

    Special Occasion

     Gracelyn embodies chic sophistication for your next black-tie gala! She features a sleeveless, criss-cross neckline, and a fitted bodice. The high waist seam leads to a form-fitting midi skirt with a center back slit and zipper closure. She is composed of a crepe knit fabric with a moderate stretch and inner lining. Complete the look in statement earrings and sleek pumps. 

    Fit & Features

    • Sleeveless, criss-cross neckline, fitted bodice
    • Bra-friendly design
    • Form-fitting
    • Midi-length hem
    • Center back slit, zipper closure
    • Crepe knit fabric, moderate stretch, inner lining
    • Fits true to size

    Style Number/Barcode: 05001-0967

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sea Breeze Tropical Midi Dress

    Take a sunset stroll in this alluring tropical midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched detailing down one side, and a midi-length, asymmetrical hem creating a high side slit. The all-over palm leaf print will bring major vacay vibes. Style with strappy sandals and a flowy kimono.

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Ruching down one side
    • Midi-length, asymmetrical hem, side slit
    • Curve-hugging silhouette
    • Palm leaf print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4421

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Natural Growth Floral Midi Dress

    Fresh florals for the new season! Bare your shoulders in this sleeveless midi dress featuring a v-neck, adjustable criss-cross spaghetti straps, and a form-fitting silhouette leading to the asymmetrical slit with a ruched seam. Complete the look in stiletto PVC mules.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Form-fitting silhouette
    • Asymmetrical slit, ruched seam
    • Midi-length hem
    • Floral print brushed stretch-knit
    • Runs true to size

    Style Number/Barcode: 05101-1498

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Brenley Mesh Keyhole Halter Midi Dress

    Special Occasion

    Flaunt your curves in the Brenley Mesh Keyhole Halter Midi dress for an unforgettable night! She features a sultry keyhole halter neckline atop the fitted bodice that leads to a showstopping silhouette with ruched seams. Show a little leg off in her midi-length hem with a front slit accent. Composed of mesh-knit lined fabric with a moderate stretch. Finish your look with sparkly earrings and stilettos. 

    Fit & Features

    • Halter neckline, keyhole cutout
    • Adhesive bra recommended
    • Fitted bodice, ruched seams
    • Form-fitting silhouette 
    • Front slit, midi hem
    • Mesh-lined knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05001-0973

    Category Name: Midi Dresses

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Floral V-Neck Midi Dress

    Look so fine in this floral midi dress perfect for creating a head-turning moment at graduation! It features a sleeveless, v-neck, spaghetti straps that cross in the back and a bodycon silhouette on a midi-length hem with a slit accent. 

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Bodycon silhouette
    • Slit front accent
    • Midi-length hem
    • Floral pattern
    • Fits true to size

    Style Number/Barcode: 05101-1553

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • New Classic Satin Slit Midi Dress

    This old thing? Slip into this sultry satin midi dress perfect for a dressy night out! The knee-length dress features a sleeveless, square neck, spaghetti straps, a form-fitting silhouette with pleating, and a front slit accent. Complete the look in sparkly heels.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Form-fitting silhouette
    • Pleat detailing
    • Front slit accent
    • Midi-length hem
    • Luxe satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1442

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Nights V-Neck Midi Dress

    Enjoy your nights in paradise in this tropical floral midi dress featuring a sleeveless, v-neck, adjustable criss-cross spaghetti straps, and a bodycon silhouette leading to the asymmetrical slit hem. Complete your vacay look in strappy heels.

    Fit & Features

    • Sleeveless, v-neck
    • Adjustable criss-cross spaghetti straps
    • Bodycon silhouette
    • Asymmetrical slit, side ruching
    • Midi-length hem
    • Tropical floral print, texture-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1455

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Lovestruck Lace Midi Dress

    Love is in the air with this stunning lace dress! The dress features a floral lace pattern, a sleeveless V-neckline with padded cups, adjustable spaghetti straps, an empire waist, and a midi-length silhouette with a high side slit. The dress is composed of a lined lace fabric that offers a form-hugging fit with minimal stretch. Complete the look with heels and rhinestone studs

    Fit & Features

    • Sleeveless V-neckline, padded cups
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Empire waist
    • Midi-length hem, high side slit, form-hugging fit
    • Sheer lace fabric, floral pattern, scalloped trim
    • Full knit lining, minimal stretch 
    • Runs true to size 

    Style Number/Barcode: 05101-1476

    Category Name: Midi Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Love At First Twirl Halter Corset Satin Midi Dress

    She’s giving hopeless romantic but still knows how to steal the spotlight. With a dreamy plunge neckline and lace-up back, this corset satin midi dress was made for picture-perfect moments as the bride-to-be, birthday girl, or guest!

    Fit & Features

    • Silky satin fabric, multiple woven and tulle linings
    • Plunge halter neckline, tie strap, underwire bust
    • Corset bodice, flexible boning
    • Lace-up back, side zipper and hook-eye closure
    • A-line voluminous silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000523

    Category Name: Midi Dresses

    Price: $31.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Carly Formal Sequin V-Neck Dress

    Special Occasion

    Turn heads in the Carly formal sequin dress sure to leave every room dazzled! She features a sleek, sleeveless, V-neck, bungee spaghetti straps, and a form-fitting silhouette on a mid-length hem. The formal dress is composed of a mesh-lined fabric with minimal stretch. Complete the look in chic hoop earrings and lucite heels.

    Fit & Features

    • Sleeveless V-neck, bungee spaghetti straps
    • Form-fitting silhouette, midi-length hem
    • Back zipper closure
    • Sequin embroidery
    • Mesh-lined fabric, minimal stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1011

    Category Name: Midi Dresses

    Price: $29.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sunset Walk Floral Midi Dress

    Take a stroll at sunset on your relaxing vacay in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, an asymmetrical midi-length hem creating an alluring side slit, and a curve-hugging silhouette. The all-over tropical floral print pairs perfectly with strappy sandals. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, cross-back design
    • Asymmetrical midi-length hem, ruching, side slit
    • Form-fitting silhouette
    • Tropical floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4374

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Romance Floral Midi Dress

    Bring the romance in this gorgeous and chic floral midi dress. It features a sleeveless square neckline, spaghetti straps, a midi-length, curve-hugging silhouette, and an all-over blooming floral print. Style this dress with sleek hoops and heeled mules.

    Shop Maxi Dress: Date Night Chic Floral Maxi Dress

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Midi-length, form-fitting silhouette
    • Floral print
    • Stretch knit fabric, inner lining
    • Runs true to size

    Style Number/Barcode: 05101-1444

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Getaway Floral Midi Dress

    Pack this adorable floral printed midi dress in your carry-on for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, ruched detailing down one side leading to a slit, and a midi-length, curve-hugging fit. Style this dress with your fave oversized shades and espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down one side leading to a slit, adjustable drawstring
    • Midi-length, form-fitting silhouette
    • All-over floral print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4383

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale