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.

  • Sweetheart Velvet Glitter Midi Dress

    Sweetheart you are a true stunner! Designed with adjustable spaghetti straps, a sweetheart neckline, padded and structured cups, and a form fitting silhouette this midi dress is a ten out of ten. Composed of a velvet material that offers moderate stretch and is embellished with silver glitter reflects throughout. Dress is fully lined and has a zipper closure with a hook and eye to keep dress in place all night long!

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

    Style Number/Barcode: 05101-0186

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Jezebel Velvet Burnout Midi Dress

    Special Occasion

    Get a little frisky in our Jezebel!

    Fits & Features

    • Deep V Neckline
    • Long Sleeve
    • Long Hemline That Meets Mid-Length 
    • High Slit At Side
    • Inner Bodysuit 
    • Mesh Composition With Velvet Burnout Detail
    • Form-Fitting Silhouette I 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: 05001-0276

    Category Name: Midi Dresses

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Season Of Sequins Dress

    This holiday season, it's all about the sequins!

    Fits & Features

    • Adjustable Spaghetti Straps 
    • Sweetheart Neckline With Bust Seam Detailing I Padded Cups
    • Zipper With Hook & Eye Closure At Back
    • Sheer Mesh Fabric With Intricate Patterns Of Sequins
    • Fully Lined 
    • Form-Hugging Fit I Plenty Of Stretch

     

    Navy And Hunter: Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

     

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

    Style Number/Barcode: 05103-0394

    Category Name: Midi Dresses

    Price: $20.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • V Neck Front Knot Midi Dress

    Toss on some heels and you've got yourself a look! This dress features a V-neckline and decorative center front knot, short sleeves, and a midi-length silhouette with front slit. Composed of a stretchy and smooth textured knit, it offers a form hugging fit and ample stretch. 

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

    Style Number/Barcode: 05102-0369

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Budding Romance Flocked Tube Midi Dress

    The attraction is real. This dress is an absolute must-have to include in your wardrobe! It features a strapless tube neckline and a midi length silhouette with a front slit. Composed of a knit fabric, it showcases flocked velvet floral patterns against the knit background. It offers a moderate amount of stretch. 

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

    Style Number/Barcode: 05101-0089

    Category Name: Midi Dresses

    Price: $13.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Look Abstract Striped Knit Midi Sweater Dress

    Create a trendy look for casual outings with this knit midi sweater dress with an abstract striped jacquard pattern for a bold vibe. It features a square neckline, long fitted sleeves, a back slit accent, and a midi-length bodycon silhouette to highlight your curves.

    Fit & Features

    • Knit fabric
    • Abstract striped jacquard pattern
    • Square neckline
    • Long fitted sleeves
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2140

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Lilith Satin Cutout Wrap-Front Midi Dress

    Special Occasion

    Chic and curve-hugging, the Lilith satin formal dress brings sleek confidence with its bodycon silhouette and sculptural details. A softly draped cowl neckline pairs with a striking cutout waist and wrap-front slit—because blending in was never the plan.

    With a smooth, luminous finish, this dress was made to shine. Keep the luxe look going with breathtaking satin prom dresses or go for a sophisticated statement with our wedding guest dresses.

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining
    • Pleated cowl neckline, padded bra cups
    • Spaghetti straps, back zipper closure
    • Underbust cutout
    • Pleated faux wrap-front design, high side slit
    • Midi-length bodycon silhouette
    • Runs true to size

     

    Where to Wear:

    School dances, weddings, bridal showers, engagement parties, rehearsal dinners, date nights, birthdays, dinner parties, galas, black tie events, milestone celebrations

    Style Number/Barcode: 05001-2574

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: ROYAL, IVORY, WHITE

    Available Size: XS, XL, S

  • Kiabeth Off Shoulder Midi Dress

    Special Occasion 

    Show those shoulders in our elegant Kiabeth midi dress!

    Fits & Features 

    • Fold Over, Off Shoulder Neckline
    • Short And Straight Off Shoulder Sleeves
    • Fitted Bodice With Vertical Seams 
    • High Waist Skirt
    • Mid-length Hem That Hits Mid Calf
    • Crepe Fabric
    • Moderate Stretch, Form Hugging Fit 

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

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

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-0290

      Category Name: Midi Dresses

      Price: $19.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Sale
    • Mock Neck Belted Sweater Dress

      Look effortless in this one-and-done sweater dress! It features a trendy mock neckline, long sleeves, a removable stylish D-ring belt along the waist, slits at the sides, and a midi-length silhouette. The garment is composed of a ribbed knit and offers a form hugging fit with an ample amount of stretch. 

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

      Style Number/Barcode: 06005-0391

      Category Name: Midi Dresses

      Price: $16.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Just A Midi Sweater Dress
      A perfect addition to your fall and winter wardrobe. Toss on a pair of booties during the day and swap them for heels during a night out! It features a mock neckline with merrow edge trim, raglan long sleeves, and a midi-length silhouette. The form-fitting dress is crafted from a ribbed knit and offers ample stretch. 

      Style Number/Barcode: 06005-0393

      Category Name: Midi Dresses

      Price: $15.97 $39.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Stylishly Fierce Satin Midi Dress

      Stay stylishly fierce in this midi-length slip dress! The dress features adjustable shoulder straps, sleeveless bodice, square back with hidden zipper and hook and eye closure, cowl neckline, thigh-high slit formed by the wrap front, and a mid-length flowy fit. Composed of smooth satin with jacquard leopard print throughout, it offers no stretch. 

      Model is 5'8" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.

      Style Number/Barcode: 05101-0535

      Category Name: Midi Dresses

      Price: $9.97 $48.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ruched One Shoulder Midi Dress

      Keep it fab and ruched with this sleek midi dress! It features a one shoulder neckline, a fitted long sleeve, a ruched left side seam and a midi length silhouette. Dress is composed of a double lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Zipper not included. 

       

      Style Number/Barcode: 05101-0412

      Category Name: Midi Dresses

      Price: $13.97 $34.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ingrid Lurex X Front Dress

      Special Occasion

      Show off those shoulders and sparkle all night long in our elegant Ingrid dress! She has a body con construction and features a dramatic, draped X-front neckline, a tank-style back with zip closure, and a seamed, midi-length skirt with a small front slit.

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-0317

      Category Name: Midi Dresses

      Price: $19.97 $44.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Tarryn Bring the Sparkle Heat Stone Midi Dress

      Special Occasion 

      Bring the sparkle to light up the night in this dazzling midi dress! It features a sleeveless bodice, a plunging sweetheart neckline with a built in no slip strip, molded padded cups with underwire for support and a double row of spaghetti straps. The slim fit bodice leads to a curve hugging midi length silhouette. Dress is composed of a sheer mesh fabric embellished with heat stones throughout. Includes a bodysuit-like contrast bottom lining and a back zipper closure. Garment offers a curve hugging fit with a moderate stretch.

      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: 05001-0154

      Category Name: Midi Dresses

      Price: $29.97 $79.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Iridescent Dream Midi Dress

      Dazzle any event in the Iridescent Dream midi dress! This dress features fixed shoulder straps, a scoop neckline, and a midi length silhouette. The garment is composed of a rib knit and showcases iridescent, shimmering sequins throughout. Form-fitting, it offers a moderate amount of stretch and does not include a zipper. 

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

      Style Number/Barcode: 05103-0626

      Category Name: Midi Dresses

      Price: $16.97 $42.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • The Essential High-Slit Ribbed Knit Midi Dress

      The ribbed knit dress features a turtleneck, fitted long sleeves, and a midi-length hem accented with a high side slit. Pair it with ankle booties to complete the look. 

      Fit & Features

      • Ribbed knit fabrication, stretchy knit lining
      • Turtleneck
      • Long sleeves
      • High side slit
      • Midi length hem
      • Runs true to size

      Style Number/Barcode: 05102-5959

      Category Name: Midi Dresses

      Price: $42.90

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Valerie Convertible Bodycon Midi Formal Dress

      Special Occasion

      Versatility at its finest, the Valerie midi formal dress offers multiple styling options to suit your mood for any formal occasion! She boasts a convertible-style neckline with straps that can be worn as a halter, one shoulder, and more, a bodycon midi silhouette that flatters your curves, and a center back slit for movement. Complete the look in stiletto heels and teardrop earrings.

      Fit & Features

      • Stretchy sleek knit fabric
      • Convertible neckline with straps
      • Multiple styling options
      • Bodycon silhouette
      • Center back slit
      • Midi-length 
      • Runs true to size

      Style Number/Barcode: 05001-1930

      Category Name: Midi Dresses

      Price: $56.90

      Availability: In Stock

      Available Color: OLIVE, BLACK

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

    • Ruched Right In Midi Dress

      Slip right into this curve-flattering midi dress. It features fixed shoulder straps, a scoop neck and back, ruching down the side seams, and a midi-length silhouette. The garment is composed of a sleek and smooth knit, and offers a moderate amount of stretch. Zipper not included. 

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

      Style Number/Barcode: 05102-0411

      Category Name: Midi Dresses

      Price: $13.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • V Mine Ribbed Knit Midi Dress

      What's not to love about this perfect layering piece? With unlimited styling possibilities, this dress features a v-neckline, long sleeves, and a midi-length silhouette. The garment is composed of a rib-knit construction and offers a form hugging fit with an ample amount of stretch. 

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

      Style Number/Barcode: 05102-0346

      Category Name: Midi Dresses

      Price: $9.97 $25.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Ribbed Knit Cut Out Midi Dress

      Ward off the chill with this cozy for keeps midi-length dress.

      Fits & Features

      • Plunging V Neckline
      • Long Sleeves
      • Large Cut-Out Detail At Back
      • Soft Knit Fabric I Fully Lined
      • Ample Stretch
      • Zipper Not Included

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

      Style Number/Barcode: 05102-0361

      Category Name: Midi Dresses

      Price: $13.97 $33.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Square Neck Long Sleeve Midi Dress

      The pairing possibilities are endless with this simple and chic piece!

      Fits & Features

      • Square Neckline
      • Long Sleeves
      • Midi Length Silhouette
      • Smooth Knit Fabric
      • Form Hugging Fit I Ample Stretch
      • Zipper Not Included

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

      Style Number/Barcode: 05102-0379

      Category Name: Midi Dresses

      Price: $9.97 $30.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Layla Formal Sequin Midi Dress

      Special Occasion

      Bring the shine to match your glam taste in our sparkling Layla dress! She features an off the shoulder neckline, short sleeves, a natural fit waist and a curve hugging midi length silhouette with bold side slit. Dress is composed of a lined mesh fabric adorned with sequins throughout. Garment offers a minimal stretch and includes a back zipper closure.

       

      Special Occasion products cannot be returned to any retail locations.

      Style Number/Barcode: 05001-4093

      Category Name: Midi Dresses

      Price: $19.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Here's The Scoop Front Slit Midi Dress

      This sultry dress is the epitome of when comfy meets chic! It features a scoop neckline, fitted long sleeves, decorative multi-row button detail, and a midi length silhouette with side slit detail. Composed of a midweight rib-knit fabric, it offers a curve-hugging fit with an ample amount of stretch. Zipper not included. 

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

      Style Number/Barcode: 06005-0206

      Category Name: Midi Dresses

      Price: $16.97 $41.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Melanie Formal Sequin Midi Dress

      Special Occasion

      Bring the sparkle with our enchanting Melanie dress! She features a sleeveless bodice, a plunging V neckline, tank-like straps and a midi length silhouette  with a high side slit. The all over sequins are set in a captivating scroll print pattern. Dress is composed of mesh knit fabric that offers a relaxed fit.

      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: 05001-0237

      Category Name: Midi Dresses

      Price: $19.97 $69.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free