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.

  • Spot On A-Line Midi Dress

    Throw on a cozy knit sweater, add a pair of boots, and your outfit will be looking spot on! Showcasing a smudge spot print, the sleeveless bodice features adjustable shoulder straps and a v-neckline. Decorative buttons trail down the front, leading to a center split. Linen crafted, this dress features an A-line silhouette and offers little to no stretch. Zipper at center back. 

     Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0301

    Category Name: Midi Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Enchanted Allure Velvet Corset Midi Dress

    The velvet dress features a sweetheart neckline with lace trim, a corset bodice with flexible boning, fitted long sleeves, and a midi-length hem accented with a high side slit. Complete the semi-formal outfit with strappy stiletto heels.  

    Fit & Features

    • Lined velvet fabrication
    • Sweetheart neckline with lace trim
    • Corset bodice with flexible boning
    • Long sleeves
    • High side slit
    • Midi length hem
    • Runs true to hem

    Style Number/Barcode: 05101-3848

    Category Name: Midi Dresses

    Price: $44.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Long Sleeve Ribbed Mini Dress

    Keep it cozy with this pretty knit dress! It features a plunging V neckline, long puff sleeves and a mini length silhouette. Dress is composed of a ribbed knit fabric that offers a form hugging fit. 

    Burgundy: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Hunter: Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0365

    Category Name: Midi Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Turtleneck Long Sleeve Ribbed Knit Mini Dress

    Bundle up to this ribbed knit mini for those cool nights. This cozy number features a turtleneck, long sleeves, scalloped hem, and mini length silhouette. The ribbed knit construction offers ample stretch. Zipper not included. 

     Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0308

    Category Name: Midi Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cowl Neck Velvet Midi Dress

    Make a statement in this velvety piece. It features fixed spaghetti straps dropping down to a trendy cowl neckline and leads right into a midi length silhouette. The garment is composed of a rib knit lining and offers a curve-hugging fit with moderate stretch.  

     

    Style Number/Barcode: 05101-0076

    Category Name: Midi Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bouquet Toss Scuba Midi Dress

    This scuba-crafted midi length dress is the prettiest pick! It showcases an all-over floral print design against a black background, scoop neckline, and back. The garment is a smooth woven construction, fully lined with a moderate stretch fit.

     Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0286

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Burnout Flocked Velvet Midi Dress

    Turn heads in this sparkly number! This dress features a plunging v-neckline, long sleeves, and a midi length silhouette. The garment is composed of burnout flocked velvet throughout, fully lined, and has a curve-hugging fit with a slight stretch. 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0204

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • One Sleeve Satin Midi Dress

    Keep it stunning in sophisticated satin! Dress features a one shoulder neckline, a fitted long sleeve, princess seams at the bust and a midi length silhouette. Dress is composed of a lined satin-like fabric that offers a form hugging fit with a slight stretch. Includes a back zipper closure with hook and eye closure. 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

     

    Style Number/Barcode: 05101-0299

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Ribbed Knit Midi Dress

    Dress up down or up with a basic midi this season girl! The dress features a mock neck, long sleeves and a midi length silhouette with a high side slit. Dress is composed of ribbed knit fabric that offers a form hugging fit with plenty of stretch. Perfect to pair with booties! 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0276

    Category Name: Midi Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cosmic Chic Tie-Dye Knit Midi Dress

    The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe. 

    Fit & Features

    • Ribbed knit fabrication
    • Scoop neckline
    • Long sleeves
    • Tie-dye pattern
    • Center slit at back of hem
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 06005-2132

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Stunning Sophistication Satin Midi Dress

    Mesmerize them all with this super gorge midi dress! It features a sleeveless bodice, a cowl neck, spaghetti straps that lead to a square back and a fitted bodice that leads to a midi length silhouette. Dress is composed of a lined satin fabric that offers a form hugging fit with a slight stretch. Zipper not included.

     

    Style Number/Barcode: 05101-0277

    Category Name: Midi Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sophisticated Enchantment Velvet Midi Dress

    The velvet dress features a sleeveless sweetheart neckline, a pleated bodice, and a midi-length hem. Complete the look with rhinestone earrings for the perfect wedding guest outfit.

    Fit & Features

    • Velvet fabrication
    • Sleeveless sweetheart neckline
    • Pleated bodice
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3733

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L, XL

  • Long Sleeve Ribbed Knit Midi Dress

    Keep it cozy and chic this season with a basic midi! This must have features a turtleneck, long sleeves and a midi length silhouette. Dress is composed of ribbed knit fabric that offers a form hugging fit with a moderate stretch. 

     

     

    Style Number/Barcode: 05102-0344

    Category Name: Midi Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Essential Sweater Dress
    Fall back on this essential sweater dress this season! It features a crew neck, long sleeves with ribbed cuffs and a midi length silhouette that pairs perfectly with booties! Dress is composed of a sweater knit fabric that offers a relaxed fit with a moderate stretch.

    Style Number/Barcode: 06005-0358

    Category Name: Midi Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleeveless Satin Scoop Midi Dress

    Serve up a sassy look with sleek satin!

    Fits & Features 

    • Scoop Neckline And Back
    • Adjustable Spaghetti Straps 
    • Curve-Hugging Midi Length Silhouette
    • Lined, Satin-Like Composition
    • Minimal Stretch 

     

    Black: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Gold: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

    Style Number/Barcode: 05101-0338

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Glitter Spaghetti Strap Mini Dress

    This bodycon features spaghetti straps, a deep v neckline, and a bodycon fit. Dress is composed of a glitter knit material that offers moderate stretch and hem hits right above the knee. Our favorite part is the sheen reflection that the glitter gives off when you catch the light!

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0408

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Ribbed Knit Midi Dress

    Dress up down or up with a basic midi this season girl! The dress features a mock neck, long sleeves and a midi length silhouette with a high side slit. Dress is composed of ribbed knit fabric that offers a form hugging fit with plenty of stretch. Perfect to pair with booties! 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0275

    Category Name: Midi Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • X Marks The Spot Midi Dress

    Look no further for the perfect night out dress! The sultry midi features a sleeveless bodice, a V neckline and a double row of spaghetti straps that leads to a cross back design. The relaxed fit bodice leads to body hugging midi silhouette that falls slightly above the knee. Dress is composed of double lined coated satin fabric that offers a moderate stretch. Zipper not included. 

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0278

    Category Name: Midi Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Swept Away Sweetheart Midi Dress

    Get swept away in stunning satin! The midi dress features a sleeveless bodice, a sweetheart neckline, wide shoulder straps and a curve hugging midi length silhouette that creates an hourglass illusion. Dress is composed of a lined satin fabric that offers a slight stretch.  

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

     

     

    Style Number/Barcode: 05101-0331

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Long Sleeve Knit Midi Dress

    Keep it basic this season! The midi dress features a V neckline, fitted long sleeves vertical stripes and a midi length silhouette that rests slightly above the knee. Dress is composed of a lined knit fabric with a form hugging fit with a slight stretch. Zipper not included. 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0395

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Gaia Satin Off-The-Shoulder Wrap Midi Dress

    Special Occasion

    The Gaia formal satin dress features a sweetheart neckline with off-the-shoulder short sleeve accents, a ruched faux wrap silhouette, and a midi-length hem. Complete your cocktail outfit with block heels.

    Fit & Features

    • Stretchy satin-knit fabrication, top knit lining
    • Off-the-shoulder neckline, short sleeve cuffs
    • Sweetheart padded bust
    • High waist seam
    • Ruched faux wrap-front design
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05001-2511

    Category Name: Midi Dresses

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: HUNTER

    Available Size: XS

    Product Badge:
    • Sale
  • Floral Desire Trumpet Midi Dress

    Bring on the florals babe! Designed with a v neckline, spaghetti straps that are adjustable, and a for fitting silhouette that leads to a ruffled trumpet high low hemline. Composed of a scuba material that offers moderate stretch and showcases a velvet floral pattern.  

     

     

    Style Number/Barcode: 05101-0125

    Category Name: Midi Dresses

    Price: $14.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Uma Heat-Stone Midi Dress

    Special Occasion 

    Slay today and everyday after! Our Uma midi dress features a form fitting silhouette, a v neckline, and spaghetti straps that lead to a square back. She is composed of a knit material with a mesh overlay adorned in heat stones, and has a side slit detail. Mesh material offers moderate stretch.

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0196

    Category Name: Midi Dresses

    Price: $19.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Scalloped Lace Trumpet Midi Dress

    Bring the flare with this flirty midi dress! It features a sleeveless bodice, a plunging V neckline with scalloped lace trim, adjustable straps that cross at the back and a midi length silhouette with a flared trumpet hem. Dress is composed of a lined lace fabric that offers a relaxed fit with minimal stretch. Includes a back zipper closure. 

    Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0304

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance