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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.

  • Striped With Style Midi Dress
    Get all striped with style with this adorable summer ready midi dress! It features a sleeveless bodice, a V neckline created by a wrap front, a partially stretchy and smocked back with a hidden zipper and hook and eye closure, a faux button down front, a waist tie, and a front slit. The mustard yellow dress is composed of lightweight woven fabric with no stretch and a short lining.

    Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0032

    Category Name: Midi Dresses

    Price: $15.00 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down In Style Dress
    Button down in style in this cute midi dress! The white dress features a square neckline, wide shoulder straps, a button down front, a tie waist belt, side pockets and a center high slit. Dress is composed of an unlined denim-like fabric that offers a form hugging fit with minimal stretch.

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

    Style Number/Barcode: 05102-0059

    Category Name: Midi Dresses

    Price: $31.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Up In Ruffles Midi Dress
    Button yourself up in pretty ruffles! This must have black dress features a sleeveless bodice, a plunging V neck with a tie front accent, ruffled shoulder straps and a multi button front with tortoise shell hued buttons. The midi length lets you show off your favorite heels! Dress us composed of a lined linen fabric that offers a relaxed fit with minimal stretch.

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

    Style Number/Barcode: 05102-0026

    Category Name: Midi Dresses

    Price: $10.00 $43.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Own The Room Striped Knit Midi Tube Dress

    Hot girl summer just got a little hotter. This striped midi tube dress hugs you in all the right places with a soft, textured knit that moves with you.

    Fit & Features

    • Striped textured cotton-blend knit fabric, lightweight knit lining
    • Moderate stretch
    • Strapless straight-across neckline
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000019

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flirty In Ruffles Midi Dress
    Keep it flirty and frilly in ruffles! This mauve dress features a sleeveless bodice, a plunging wrap V neckline with a ruffled trim, adjustable spaghetti straps, a cinching tie waist belt and an A-line midi length silhouette. Dress is composed of a lined woven fabric with no stretch.

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

    Style Number/Barcode: 05102-0030

    Category Name: Midi Dresses

    Price: $10.00 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunner In Lace Midi Dress

    Make a stunning entrance in this gorgeous lace midi dress! It features a flattering off-the-shoulder neckline with a sheer lace overlay, a high waist, and a mid-length, curve-hugging silhouette. Style this dress with pretty earrings and new heels for the perf bridal shower look!

    Fit & Features

    • Off-the-shoulder neckline, sheer lace overlay
    • High waist
    • Mid-length, form-hugging fit
    • Sheer lace fabric, full knit lining
    • Moderate stretch
    • Runs true to size

      Style Number/Barcode: 05101-8850

      Category Name: Midi Dresses

      Price: $9.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Floral Day Dream Midi Dress
      You'll be too good to be true in this gorgeous light blue midi dress. It features a V neckline, spaghetti straps that lead to a cowl back, a knit lining, a form hugging silhouette and a below the knee length. Knit fabric features a pink hued floral print, and plenty of stretch.

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

      Style Number/Barcode: 05101-8667

      Category Name: Midi Dresses

      Price: $10.00 $37.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • In Your Pipe Dreams Midi Dress
      You're the ultimate dream girl in this flattering midi dress! It has a deep V neckline, spaghetti straps leading to a square back and exposed zipper and hook and eye closure, and perfectly placed piping throughout to create a shape that complements this dress' body-hugging silhouette. Midi dress is composed of a natural-colored knit fabric and offers moderate stretch.

      Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.

      Style Number/Barcode: 05101-8666

      Category Name: Midi Dresses

      Price: $15.97 $37.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Spring Beauty Midi Dress
      Showcase your beauty with this gorgeous spring ready dress! It features a sleeveless bodice, spaghetti straps, a scalloped V neckline with padded cups, and a mid-length, form hugging fit with a matching scalloped hem. The ivory hued dress is composed of a sheer lace fabric with an embroidered floral print and includes a full nude hued lining.

      Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

      Style Number/Barcode: 05101-8651

      Category Name: Midi Dresses

      Price: $10.00 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Wrapped In Pleats Midi Dress
      Wrap yourself in pretty pleats to make a gorgeous appearance! The mini dress features a sage green color, a wrap V neckline, narrow shoulder straps and an asymmetrical wrap silhouette. Dress is composed of a crepe fabric that offers a form hugging fit with a moderate stretch. Includes a back zipper closure.

      Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05101-8615

      Category Name: Midi Dresses

      Price: $10.00 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Ready And Ruffled Midi Dress

      She's ready to work it. Cause a commotion in this midi dress!

      Fits & Features 

      • Elastic Off Shoulder Neckline
      • Ruffled Popover Detail
      • Form Hugging Silhouette
      • Midi Length Ruffled Trumpet Hemline
      • Fully Lined & Composed Of Crepe Fabric
      • 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: 05101-8114

      Category Name: Midi Dresses

      Price: $5.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Chasing Dreams Ruffle Dress
      Chase your dreams in this flowy blue ruffle dress! It features an off the shoulder neckline with a ruffle pop over, a fitted bodice with a high waist seam and tie belt detail, a hidden side zipper closure, and a flowy skirt with a double-tiered, high-low hem. Dress is composed of a woven fabric with no stretch.

      Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

      Style Number/Barcode: 05101-8202

      Category Name: Midi Dresses

      Price: $15.97 $38.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Picture Perfect Color Block Midi Dress

      For a picture-perfect look you'll be reaching for this color block midi dress for any casual plans! The strapless fitted bodice accentuates your silhouette while the flowy midi-length hem creates an elegant movement as you walk. Plus, keep your hands warm in the convenient hidden side pockets!

      Fit & Features

      • Woven cotton-blend fabric, stretchy knit lining
      • Strapless color block fitted bodice
      • Hidden side pockets
      • Back zipper and hook-eye closure
      • Flowy midi-length hem
      • Runs true to size

      Style Number/Barcode: 05102-6109

      Category Name: Midi Dresses

      Price: $9.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Painted In Florals Midi Dress
      Radiate a romantic aura in soft water colored florals! This midi length dress has an off the shoulder neckline with an elastic hem and short sleeves. Paint yourself in the gorgeous blue and mauve colored blossoms that are complimented with green foliage. Dress is composed of a soft the touch sturdy knit fabric that offers a curve hugging fit with moderate stretch. 

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

      Style Number/Barcode: 05101-7384

      Category Name: Midi Dresses

      Price: $19.97 $32.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Nights In Satin Flare Midi Dress

      Channel your inner siren in this slinky-elegant midi dress. Best paired with a seamless body-shaper for a sleek and flawless finish.

      Fits & Features

      • Adjustable Spaghetti Straps
      • Back Zip Closure
      • Cowl Neckline
      • Slightly Flared Hem
      • Unlined, Satin-Like Fabric 
      • Minimal Stretch

       

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

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

      Style Number/Barcode: 05101-0341

      Category Name: Midi Dresses

      Price: $19.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Sweetly Chic Midi Dress
      Have a sweetly chic look with this gray houndstooth print midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline, a hidden back zipper and hook and eye closure, a high waist seam, a front slit with a drawstring, and an asymmetrical hem. The dress is composed of a sheer lightweight woven fabric with a short white knit lining.

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

      Style Number/Barcode: 05101-0040

      Category Name: Midi Dresses

      Price: $17.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Maureen Formal One Shoulder Dress
      Special Occasion 

      Draw all eyes on you the moment you enter the room in our wowing Maureen black dress! She features a one shoulder neckline, a fitted long sleeve, a ruched side seam and an asymmetrical hem. Dress is composed of a sheer mesh fabric that is complemented with a beige hued lining to create a flattering two-tone effect. Garment offers a form hugging fit with a moderate stretch. 

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

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05002-6774

      Category Name: Midi Dresses

      Price: $19.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Selena Formal One Shoulder Ruched Dress
      Special Occasion 

      Stun with a little shoulder action as you channel sophistication in our Selena dress! She features a classic black hue, a one shoulder neckline with a single shoulder strap and a ruched side detail. Her slim fit bodice leads to an asymmetrical hem to show off your fab heel game! Dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. 

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05002-6702

      Category Name: Midi Dresses

      Price: $19.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Faith Formal Midi Lace Dress
      Special Occasion 

      Make a graceful entrance in captivating lace! Faith features an ivory hue, an off the shoulder neckline with a scalloped lace trim, padded cups, a cinching ribbon belt and a midi length. Dress is composed of a lined fabric that offers a relaxed fit with a minimal stretch. 

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

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4131

      Category Name: Midi Dresses

      Price: $19.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Alanna Formal Sequin Midi Dress
      Special Occasion 

      Shimmer and shine as you make a glam statement in the diva approved Alanna dress! She features a luxe gold hue, a plunging V neckline, padded cups, princess seams and narrow shoulder straps. Her slim fit bodice leads to a flattering midi length silhouette. Dress is composed of a lined mesh fabric adorned with sequins. Garment offers a form hugging fit with a minimal stretch. Includes a back zipper closure.

      Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4116

      Category Name: Midi Dresses

      Price: $19.97 $54.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Nayla Formal Sequin Fringe Dress
      Special Occasion 

      Bring the glam and luxe in our sparkling Nayla dress! She features a rose gold color, a V neckline with padded cups, adjustable straps and a midi length silhouette with a fringe hem. Dress is composed of a lined mesh fabric adorned with dazzling sequins throughout. Dress offers a form 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.

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4109

      Category Name: Midi Dresses

      Price: $29.97 $59.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Flawless Beauty Cutout A-Line Midi Dress

      Step out in this A-line midi dress for a flawless look all spring to summer! Designed with a sleek sweetheart neckline and underbust cutout, this dress makes a delightful impression.

      Fit & Features

      • Woven fabric
      • Sweetheart neckline
      • Adjustable spaghetti straps
      • Underbust cutout, back zipper closure
      • A-line silhouette
      • Midi-length hem
      • Runs true to size

      Style Number/Barcode: 05102-6064

      Category Name: Midi Dresses

      Price: $9.97 $52.90

      On Sale: Yes

      Availability: In Stock

      Available Color: IVORY

      Available Size: M, L

      Product Badge:
      • Sale
    • Kenia Formal Velvet Midi Dress
      Special Occasion

      Wrap yourself in luxe velvet as you allure them all in our Kenia dress! She features an all over black hue, an off the shoulder neckline, a sweetheart bust, fitted long sleeves and a midi length silhouette with a high side slit. Dress is composed of a black hued velvet fabric.

      Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small ,

      ,*Also available in Plus.
       

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4091

      Category Name: Midi Dresses

      Price: $19.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Leslie High Slit Midi Lace Dress
      Special Occasion 

      Keep it simply elegant as you make an impression in lace! Leslie features an ivory hue, an off the shoulder neckline, unlined short sleeves and a high side slit. Dress is composed of a lined lace fabric that offers a form hugging fit with a moderate stretch. Includes a back zipper closure.

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

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4087

      Category Name: Midi Dresses

      Price: $19.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance