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.

  • Misty Off Shoulder Glitter Dress

    Special Occasion

    You'll be channeling princess vibes in this one. Look magical in our glistening Misty dress! 

    Fits & Features

    • Off Shoulder Neckline I Fold Over Design
    • Back Zip With Hook & Eye Closure
    • Midi Length Silhouette I Front Slit
    • Glitter Lurex Fabric I Fully Lined
    • Curve Hugging Fit I Moderate Stretch 

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0330

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elaine Fine Dine Midi Dress
    Special Occasion 

    It's an elegant night out! This perfect midi dress features a racer front with double halter and shoulder straps, a form hugging bodycon fit and a midi length. Dress includes a hidden back zipper closure. Elaine is composed of a lined crepe fabric that offers a from hugging fit with slight stretch. Includes an additional mini skirt length knit lining.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-4028

    Category Name: Midi Dresses

    Price: $36.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sparkle Diva Glitter Wrap Mini Dress

    Sparkle like the diva you are in this dazzling mini dress! The glitter is all you need to shine all night! 

    Fit & Features

    • Wrap V-Neckline
    • Spaghetti Tie Straps 
    • Ruched
    • Glitter
    • Asymmetrical Hem 
    • Form Hugging Fit
    • Moderate Stretch 

     

     


    Style Number/Barcode: 05101-0348

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Long Sleeve Ribbed Midi Dress

    We're totally loving knit this season girl! Create some seriously cute looks with a basic midi dress! 

    Fit & Features

    • Off The Shoulder Neckline 
    • V-Neck Bust
    • Fitted Long Sleeves
    • Ribbed 
    • Knit
    • Form Hugging Fit
    • Moderate Stretch 

     

    Style Number/Barcode: 05102-0391

    Category Name: Midi Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe's A Bombshell Velvet Midi Dress

    Baby-girl you're a bombshell in velvet! This midi dress is a real head turner, with a v neckline, a mid length hemline, bungee spaghetti straps, and a form fitting silhouette. Dress is composed of a velvet fabric and offers moderate stretch. Fully lined.

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

    Style Number/Barcode: 05103-0161

    Category Name: Midi Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe's A Bombshell Velvet Midi Dress

    Baby-girl you're a bombshell in velvet! This midi dress is a real head turner, with a v neckline, a mid length hemline, bungee spaghetti straps, and a form fitting silhouette. Dress is composed of a velvet fabric and offers moderate stretch. Fully lined.

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

    Style Number/Barcode: 05103-0162

    Category Name: Midi Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Wait A Midi Satin Midi Dress

    Hold on a second..this dress is totally your style! 

    Fits & Features

    • Plunging V Neckline With Padded Cups
    • Adjustable Spaghetti Straps
    • Zipper With Hook & Eye Closure At Back
    • Asymmetrical Ruching Detail At Front Bodice
    • Midi Length Silhouette
    • Satin-Like Composition I Fully Lined 
    • Form-Hugging Fit I Moderate Stretch 

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

    Style Number/Barcode: 05101-0309

    Category Name: Midi Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Aubrey Lace-Up Slit Satin Midi Formal Dress

    Special Occasion

    Cause a scene when you're seen in the Aubrey satin midi formal dress at celebrations and banquets! The formal dress is designed with a sleek square halter neckline with spaghetti straps that shapes the lace-up open back while the bodycon silhouette boasts a flirty side slit. Pair with earrings.

    Fit & Features

    • Stretch satin fabric with full-length knit lining
    • Sleeveless square halter neckline, padded bra cups, under bust seam
    • Adjustable spaghetti straps, open lace-up back
    • Ruched lower back, zipper with hook-eye closure
    • High waist seam, front ruched seam, high slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2611

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: ROYAL

    Available Size: L

  • Feeling Knit Asymmetrical Mini Dress

    We're feeling this super cute mini dress! Pair with your favorite accessories to complete a chic look! 

    Fit & Features

    • Square Neckline
    • Spaghetti Straps 
    • Asymmetrical Hem
    • Mini 
    • Smooth Knit
    • Form Hugging Fit
    • Moderate Stretch 

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

    Style Number/Barcode: 05103-0669

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Always V Mine Midi Dress

    You can never go wrong with a V cut neckline. Show some love and flaunt this flirty velvet midi! 

    Fits & Features

    • Deep V Neckline
    • Double Spaghetti Straps
    • Princess Seams At The Bust I Padded Cups
    • Zipper & Hook And Eye Closure
    • Midi Length Silhouette With Slit At Front
    • Velvet Composition I Fully Lined
    • Form Hugging Fit With Moderate Stretch 

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

      Style Number/Barcode: 05101-0207

      Category Name: Midi Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Sleeveless Draped Asymmetrical Wrap Dress

      Wrap yourself in this sexy mini dress for a night out with the squad girl! 

      • Cowl Neck
      • Spaghetti Straps
      • Ruching 
      • Asymmetrical 
      • Midi Silhouette 
      • Form Hugging | Moderate Stretch 

       

      Style Number/Barcode: 05101-0364

      Category Name: Midi Dresses

      Price: $9.97 $36.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Clearance
    • Lavish Leopard Print Midi Dress

      So fierce, so fab! Embrace the trendy leopard print and highlight all your right curves in the Lavish Leopard Print midi dress. 

      Fits & Features

      • Adjustable Spaghetti Straps
      • Cowl Neckline
      • Square Back
      • Ruching Drawstring Along The Sides
      • Textured Satin-Like Composition 
      • Midi Length Silhouette
      • Form Hugging Fit I Little-To-No-Stretch

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

        Style Number/Barcode: 05101-0563

        Category Name: Midi Dresses

        Price: $19.97 $48.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Clearance
      • Trumpet Hem Satin Midi Dress

        Looking for an elegant style that's still got a bit of flare? This midi is all about a streamlined look with a hint of drama! 

        Fits & Features

        • Plunging V-Neckline I Square Back
        • Spaghetti Straps
        • Vertical Dart Seams At Bust
        • Midi, High-Low Trumpet Hem 
        • Satin-Like Composition I Fully Lined
        • Form-Hugging Silhouette I Moderate Stretch 

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

          Style Number/Barcode: 05101-0332

          Category Name: Midi Dresses

          Price: $15.97 $39.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Sequin Diva Midi Dress

          Steal the spotlight and werk it in this diva-licious sequin dress!

          Fits & Features

          • Mock Neckline
          • Cap Sleeves
          • Zipper At Back
          • Conservative Midi Length
          • Sheer Mesh Fabric Embellished With Sequin Design I Fully Lined
          • Curve Hugging Fit I Offers Minimal Stretch 

          Model is 5'9 with a 32" bust, 24" waist and 36" hips. She is wearing a size small.

          Style Number/Barcode: 05101-7627

          Category Name: Midi Dresses

          Price: $9.97 $59.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Set The Record Straight Pinstripe Midi Dress

          It's a done deal. You'll be wanting to head straight to the party in this sultry midi!

          Fits & Features

          • V-Neckline
          • Adjustable Shoulder Straps
          • Zipper & Hook And Eye Closure At Back 
          • Fully Lined, Velvet Composition I Glitter Pinstripe Design Throughout
          • Front Thigh High Slit 
          • Form-Hugging Fit I Moderate Stretch

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

          Style Number/Barcode: 05101-0236

          Category Name: Midi Dresses

          Price: $9.97 $42.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Spotlight Stealin' Satin Mini Dress

          YASSS. You go steal the spotlight in that satin mini dress bby! 

          Fit & Features

          • V- neckline | Spaghetti straps
          • Vertical seams down the center
          • Ruche Detailing
          • Satin 
          • Minimal stretch
          • No Zipper
          • Mid-length

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

            Style Number/Barcode: 05101-0380

            Category Name: Midi Dresses

            Price: $9.97 $37.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Ignite The Charm Strapless Slit Midi Dress

            A strapless midi dress featuring a cowl neckline with padded bra cups for support, side ruched seams that define your curves along the bodycon fit with a side slit. The sleek knit fabric offers plenty of stretch and comfort. 

            Fit & Features

            • Knit fabric, moderate stretch
            • Strapless cowl neckline
            • Padded bra cups
            • Side ruched seams
            • Side slit
            • Bodycon fit, midi-length hem
            • Runs true to size

            Style Number/Barcode: 05101-4057

            Category Name: Midi Dresses

            Price: $35.90

            Availability: In Stock

            Available Color: SAGE-2, SAGE

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

          • Anita Mock Neck Ruched Midi Dress

            Special Occasion 

            Accentuate all your curves in the Anita midi dress!

            Fits & Features

            • Mock Neckline
            • Long Fitted Sleeves
            • Ruching Throughout Front
            • Midi Length Silhouette
            • Jersey Knit Composition 
            • Bodycon Fit I Moderate Stretch
            • Zipper Not Included

             

            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: 05001-0319

            Category Name: Midi Dresses

            Price: $19.97 $44.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Ships Free
          • Sculpted Chic Ribbed Knit Midi Dress

            The ribbed knit dress features a sweetheart neckline with a twist accent at the bust, long sleeves, and a midi-length hem. Channel a casual vibe with chunky sneakers. 

            Fit & Features

            • Ribbed knit fabrication
            • Sweetheart neckline with twist accent
            • Long sleeves
            • Midi length hem
            • Runs true to size

            Style Number/Barcode: 05102-5962

            Category Name: Midi Dresses

            Price: $44.90

            Availability: In Stock

            Available Color: GRAY

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

          • Scooped In Glam Glitter Midi Dress

            Get scooped up in this glam midi dress! 

            Fit & Features

            • Scoop Neckline
            • Spaghetti Straps 
            • Glitter
            • Leaf Print Design
            • Lined Velvet 
            • Form Hugging Fit
            • Moderate Stretch 

             

            Style Number/Barcode: 05101-0343

            Category Name: Midi Dresses

            Price: $13.97 $35.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Shine & Divine Ruffle High-Low Dress

            Sleek and polished, the Shine & Divine High-Low dress is just what you need for an effortless look! 

            Fits & Features

            • Wrap V-Neckline
            • Spaghetti Straps With Criss Cross Design At Back 
            • High-Low, Ruffle Trim Hem 
            • Smooth Satin-Like Composition I Fully Lined
            • Form Flattering Fit
            • Plenty Of Stretch 

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

            Style Number/Barcode: 05101-0390

            Category Name: Midi Dresses

            Price: $9.97 $37.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Will You Be My Sweetheart Midi Trumpet Dress

            Hey girl, will you be my sweetheart? Because you look like you're quite the romantic! 

            Fit & Features

            • Off shoulder
            • Fold over sweetheart neckline
            • Form fitting silhouette
            • Crepe
            • Moderate stretch
            • Midi length
            • Trumpet flared hemline

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

            Style Number/Barcode: 05101-0267

            Category Name: Midi Dresses

            Price: $15.97 $39.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Sleek Chic Satin Midi Dress

            Slay it in satin! You'll be wanting to put this midi on repeat.

            Fits & Features

            • Tank-Inspired Straps
            • V-Neckline I Elastic Square Back
            • Vertical Seams At The Bust
            • Midi Length Silhouette
            • Satin-Like Composition 
            • Bodycon Fit I Moderate Stretch 

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

                Style Number/Barcode: 05101-0394

                Category Name: Midi Dresses

                Price: $11.97 $29.90

                On Sale: Yes

                Availability: Out of Stock

                Product Badge:
                • Clearance
              • Glitter Galore Midi Dress

                Slay all day in the Glitter Galore midi dress!

                Fits & Features

                • Sweetheart Neckline
                • Double Strap Hook & Eye Closure At Back
                • Cut-Out Details Along Sides And Back
                • Fully Lined, Glitter Knit Composition
                • Curve-Hugging Fit I Moderate Stretch
                • Zipper Not Included

                 

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

                Style Number/Barcode: 05101-0294

                Category Name: Midi Dresses

                Price: $14.97 $36.90

                On Sale: Yes

                Availability: Out of Stock

                Product Badge:
                • Clearance