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.

  • Chain My Mind Side Slit Midi Dress

    This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.

    Fit & Features

    • Sleeveless square neck
    • Chain link adjustable spaghetti straps
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4800

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Mode Activated Cutout Lace Midi Dress

    This midi dress? It didn’t come to play—it came to slay. With flirty lace trim, flirty cutouts, and a leg-baring slit, this midi’s your go-to for nights that need a little spice.

    Fit & Features

    • Mesh-lined knit fabric with stretch
    • Sweetheart neckline with lace trim straps
    • Underbust and back cutout with lace detail
    • High side slit, bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000399

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Cocktail Hour Satin Midi Dress

    Elevate your look for cocktail hour with this sleek satin midi dress! It features a sleeveless V-neckline, dual spaghetti straps that lead to a cross-back design, a midi-length hem with a curve-hugging bodycon silhouette, and a chic high side slit. Style with strappy stilettos.

    Fit & Features

    • Sleeveless V-neckline
    • Dual spaghetti straps, cross-back design
    • Midi-length hem, fitted bodycon silhouette
    • High side slit
    • Smooth satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1766

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Luxe Sleek Vibes Satin Midi Dress

    Bring the luxe sleek vibes to your look with this stunning satin midi dress. The knee-length dress features a sleeveless sweetheart neckline with padded cups, adjustable spaghetti straps, a fitted high waist seam, ruched detailing down one side, a midi-length asymmetrical hem creating a chic side slit, and a curve-hugging silhouette. Complete the outfit with strappy stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline, padded cups
    • Adjustable spaghetti straps
    • Fitted high waist seam
    • Ruching down one side
    • Midi-length, asymmetrical hem, side slit
    • Form-fitting silhouette
    • Smooth satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1603

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Minimalistic Sultry Midi Dress

    Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps
    • Curve-hugging silhouette
    • Front slit accent
    • Midi-length hem
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4782

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Work Of Art Marble Midi Dress

    Girl, your taste is a work of art! Step out in a midi dress that features a gorge marble print, a sleeveless scoop neckline with bungee spaghetti straps, and a midi length hem with ruching throughout. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a quilted crossbody. 

    Fit & Features

    • Sleeveless scoop neckline
    • Bungee spaghetti straps
    • Marble print
    • Ruching
    • Midi-length hem
    • Lined mesh fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4732

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • It-Girl Status Midi Dress

    Showcase major it-girl status in this chic lace-up midi dress. It features a sleeveless scoop neckline, tank shoulder straps, an open back with a cross-back lace-up strappy design, a midi-length hem, and a curve-hugging silhouette. Style with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Open back, cross-back lace-up strappy design, tie closure
    • Midi-length hem
    • Form-fitting, bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4489

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • She's Got Bold Style Midi Dress

    Showcase your fearless bold style in this alluring and chic midi dress! It features a sleeveless one-shoulder neckline with an asymmetrical shoulder strap, a center O-ring cutout, dual waist cutouts, and a midi-length, curve-hugging silhouette with a thigh-high side slit. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Asymmetrical single shoulder strap
    • Center O-ring cutout
    • Dual waist cutouts
    • Midi-length hem, bodycon silhouette, high side slit
    • Smooth knit fabric, partial knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4774

    Category Name: Midi Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Shine Sequin Midi Dress

    Bring the shine in this sultry-chic sequin midi dress! It features a sleeveless V-neckline, dual bungee spaghetti straps, an open back with a cross-back strappy design, and a midi-length, curve-hugging silhouette with a thigh-high front slit. The lined mesh fabric features all-over sequin embroidery. Style with glitzy rhinestone earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Dual bungee spaghetti straps
    • Open back, cross-back strappy design
    • Midi-length hem, fitted bodycon silhouette, high front slit
    • Sheer mesh fabric, full knit lining, moderate stretch
    • All-over sequin embroidery
    • Runs true to size

    Style Number/Barcode: 05101-1652

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Glamour Mesh Midi Dress

    Keep all eyes on you in this sultry glam mesh midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, piping at the bust to give the illusion of a corset design, ruching down the side seams, and a midi-length bodycon silhouette that will hug your curves. Style with a pair of strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spgahetti straps, back zipper, hook and eye closure
    • Piping at the bust, corset design, high waist seam
    • Ruching down the side seams
    • Midi-length hem, back slit accent, fitted bodycon silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1788

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Martine Off-The-Shoulder Midi Satin Formal Dress

    Special Occasion

    Look your most glamorous and chic in the Martine satin midi formal dress showcasing a floral applique along the bust with faux pearl accents and a lace-up back that turns heads!

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining
    • Off-the-shoulder neckline, floral and faux pearl applique
    • Padded bra cups, short-sleeve cuffs
    • Back lace-up, lower zipper and hook-eye closure
    • Front wrap slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, bridesmaids, romantic date nights, cocktail parties, formal celebrations

    Style Number/Barcode: 05001-2748

    Category Name: Midi Dresses

    Price: $69.90

    Availability: In Stock

    Available Color: ROSE, GOLD, NAVY

    Available Size: XS, S, M, L

  • Bold Vibes Cutout Midi Dress

    Bring the bold vibes to your sultry night out 'fit in this alluring midi dress. It features a sleeveless one-shoulder neckline, a single tank shoulder strap with a front cutout accent, an asymmetrical side cutout at the waist, and a midi-length, curve-hugging silhouette with a high front slit. Style with strappy heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Single tank shoulder strap, front cutout
    • Asymmetrical side cutout at the waist
    • Midi-length, form-fitting, bodycon silhouette
    • Front slit
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4492

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sleek Zebra Print Midi Dress

    Keep your look so sleek with a midi dress that levels up your casual outfits! It features a sleeveless V-neckline with a knot-front design, a small keyhole cutout under the bust, spaghetti straps, a midi-length, fitted, A-line sihouette, and a chic front slit. The smooth knit fabric features an all-over zebra print pattern. Stye with strappy mules.

    Fit & Features

    • Sleeveless V-neckline, knot-front design
    • Keyhole cutout under the bust
    • Spaghetti straps
    • Midi-length hem, fitted A-line silhouette
    • High front slit
    • Knit fabric, plenty of stretch
    • Zebra print
    • Runs true to size

    Style Number/Barcode: 05102-4703

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Walk My Way Glitter V-Neck Midi Dress

    Catch glances in this glittery number! The sleeveless V-neckline shapes this midi bodycon dress that features sleek bungee spaghetti straps and an asymmetrical hem with a sultry cutout slit. Complete the look in fringe earrings.

    Fit & Features

    • Sleeveless, V-neck, bungee spaghetti straps
    • Bodycon silhouette
    • Asymmetrical midi hem
    • Cutout side slit
    • Glitter knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1412

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Basic High Slit Midi Dress

    This alluring basic midi dress will easily become one of your staple styles. It features a sleeveless sweetheart neckline with a built-in padded bust, adjustable spaghetti straps for a customized fit, a midi-length bodycon silhouette, and a high side slit. Pair with a moto jacket and mules.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded bust, bust seam outline
    • Adjustable spaghetti straps
    • Midi-length hem, fitted bodycon silhouette
    • High side slit
    • Cotton-blend fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4722

    Category Name: Midi Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chantel Heat Stone Mesh Midi Dress

    Special Occasion

    Heat up the night in the alluring and chic Chantel formal dress! She features a sleeveless square neckline, bungee spaghetti straps, ruching down the side seams, and a midi-length, curve-hugging, bodycon silhouette. The lined mesh fabric features all-over iridescent heat stone embellishments for the prettiest sparkle. Style with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline, elastic band
    • Strapless or adhesive bra recommended
    • Bungee spaghetti straps
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Mini iridescent heat stone embellishments
    • Runs true to size

    Style Number/Barcode: 05001-1108

    Category Name: Midi Dresses

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Knit High Slit Midi Dress

    This elevated brushed knit midi dress will be your new go-to for a casual night out. It features a sleeveless square neckline, spaghetti straps, an alluring center cutout at the waist, a midi-length, curve-hugging fit, and a thigh-high side slit. Style with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Center cutout at the waist
    • Midi-length, form-fitting silhouette
    • High side slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4451

    Category Name: Midi Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cutie In Cap Sleeve Midi Dress

    Cute has never looked so cozy! This rib-knit midi dress is designed with cap sleeves, dual v-necklines, a bodycon silhouette, and a flirty side slit along the hem. Complete the look in sandals for a day date.

    Fit & Features

    • Cap sleeves
    • Dual v-necklines
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Stretchy rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4715

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Kourtney Glitter Bow Midi Formal Dress

    Special Occasion

    Make them stop and stare—The Kourtney formal dress is your RSVP-ready showstopper, crafted from glittering fabric with a sleek bodycon fit and a striking low back and statement bow.

    Fit & Features

    • Glitter knit fabric, stretchy knit lining
    • Square neckline, padded bra cups
    • Adjustable spaghetti straps
    • Low back with statement bow
    • Bodycon fit
    • Midi-length hem, center back slit
    • Runs true to size

     

    Where to Wear:

    Weddings, black tie galas, cocktail parties, engagement parties, rehearsal dinners, birthdays, date night, milestone celebrations, vacation, bachelorettes

    Style Number/Barcode: 05001-000279

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Take Note V-Neck Sweater Dress

    Everyone will take note of how sultry this sweater dress is on you! It features a sleeveless, v-neck, cutout bodice with wrap tie-back closure, side slit accent, and a midi, curve-hugging silhouette. Complete the look in chic strappy heels for a daytime soiree.

    Shop More Styles: The Sweater Collection

    Fit & Features

    • Sleeveless, v-neck, tank-style straps
    • Cutout bodice
    • Wrap tie-back closure
    • Side slit accent
    • Midi, curve-hugging silhouette
    • Sweater rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 06005-1488

    Category Name: Midi Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style Goals Floral Mesh Midi Dress

    Showcase total style goals in this stunning floral mesh midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a strappy design, a midi-length, curve-hugging silhouette, and a thigh-high side slit. The lined mesh fabric features all-over floral embroidery for a pretty vibe. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, horizontal strappy design
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Floral embroidery
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4738

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring And Chic Ruched Midi Dress

    Create an alluring silhouette in this chic ruched midi dress that will hug your curves. It features a sleeveless cowl neckline, bungee spaghetti straps that lead to a cross-back design, ruched detailing down the side seams, and a midi-length hem with a form-hugging fit. Style with clear mules.

    Fit & Features

    • Sleeveless cowl neckline
    • Bungee spaghetti straps, cross-back design
    • Ruching down the side seams
    • Midi-length hem, form-fitting silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4510

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Guest Of Honor Satin Midi Dress

    How could you not be the guest of honor in this sultry stunner! Make your entrance in this satin midi dress featuring a classy, sleeveless V-neck, spaghetti straps, and a pleated waist leading the form-fitting silhouette with a sexy side slit. Complete the look in a dainty ring set and heels.

    Fit & Features

    • Sleeveless V-neck, spaghetti straps
    • Pleated waist
    • Form-fitting silhouette
    • Side slit
    • Midi-length hem
    • Silky satin lined fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1561

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Knott Love Halter Cutout Midi Dress

    You'll fall for this halter midi dress with just one look! Featuring a sleeveless, halter neck with tie-back closure, a trendy knot cutout bodice that shapes the bodycon silhouette. Complete the look in classy nubuck heels.

    Fit & Features

    • Sleeveless, halter neck, tie-back closure
    • Knot cutout bodice
    • Bodycon silhouette
    • Midi-length hem
    • Soft and stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4322

    Category Name: Midi Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale