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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.

  • Easy Does Knit Midi Dress

    Let your outfit do all the talking for you! Heat up your wardrobe with this knit midi 

    Fits & Features

    • Scoop Neck
    • Fitted Long Sleeves 
    • Faux Button Down Front 
    • Midi Length Silhouette I Front Slit 
    • Ribbed Knit I 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: 05102-0442

    Category Name: Midi Dresses

    Price: $12.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Remi Sequin Wrap Dress

    Special Occasion

    You'll be illuminating every room you walk into in our stunning Remi! 

    Fits & Features

    • Dual Spaghetti Straps I Surplice V Neckline  
    • Back Zip With Hook & Eye Closure 
    • Midi Length Silhouette With Wrap Design I Mini Length Lining
    • Mesh Lined Fabric With Sequins Throughout 
    • Curve Hugging Fit I Ample Stretch  

    Model is 5'7" with a 34" 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: 05001-0339

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Adalee Formal High Slit Satin Dress

    Special Occasion 

    Keep it simply stunning in satin as you make your entrance in our Adalee dress! Her high slit brings an extra dramatic detail! 

    Fit & Features 

    • Cowl Neckline 
    • Adjustable Spaghetti Straps That Cross At The Back
    • Zipper With Hook & Eye Closure At Back
    • Midi Length Silhouette With High Slit 
    • Lined Satin 
    • Form Hugging Fit | 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: 05001-0300

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Valentina Ruched Satin Dress

    Special Occasion

    Make a stylish statement in our lovely Valentina! 

    Fits & Features

    • Spaghetti Straps That Cross & Lace-Up At The Back I Back Zip With Hook & Eye Closure
    • Plunging V Wire Neckline I Pleating Detail At Bust 
    • Midi Length Silhouette I Ruching Accent I Side Slit 
    • Satin-Like Fabric 
    • Curve Hugging Fit I 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: 05001-0336

      Category Name: Midi Dresses

      Price: $29.97 $49.90

      On Sale: Yes

      Availability: Out of Stock

      Product Badge:
      • Ships Free
    • Yvette Deep V Midi Dress

      Special Occasion

      Sparkle and shine in our glamourous Yvette! You'll be looking your absolute best in her glistening silhouette. 

      Fits & Features

      • Spaghetti Straps That Cross At The Back
      • Plunging V Neckline I Padded Bust 
      • Back Zip With Hook & Eye Closure
      • Midi Length Silhouette I Side Slit 
      • Glitter Woven Fabric 
      • Curve Hugging Fit I Moderate Stretch 
      • Glitter May Transfer 

       

      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: 05001-0343

        Category Name: Midi Dresses

        Price: $19.97 $39.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Sheila Lace-Up Satin Midi Formal Dress

        Special Occasion

        Silky satin crafts the elegant Sheila midi formal dress perfect for bridesmaids, wedding guests, or a dressy banquet! The sleeveless dress boasts a flattering V-neckline with wide shoulder straps that shape the head-turning lace-up open back while the faux wrap bodycon silhouette shows off your figure. Pair with earrings and heels.

        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

        • Silky satin fabric, sewn-in knit lining
        • V-neckline, padded bra cups
        • Wide shoulder straps
        • Lace-up open back, lower zipper and hook-eye closure
        • Faux wrap bodycon silhouette, front slit
        • Midi-length hem
        • Runs true to size

        Style Number/Barcode: 05001-2634

        Category Name: Midi Dresses

        Price: $19.97 $69.90

        On Sale: Yes

        Availability: In Stock

        Available Color: HUNTER

        Available Size: XS, S

        Product Badge:
        • Sale
      • Florence Off Shoulder Satin Dress

        Special Occasion

        Tis' the season for dressing up! Show up to your soirees in our fabulous Florence. 

        Fits & Features 

        • Off Shoulder Design
        • Back Zip With Hook & Eye Closure 
        • Sweetheart Wrap Neckline
        • Midi Length Silhouette I Front Side Slit 
        • Satin-Like Fabric I Fully Lined 
        • Curve Hugging Fit I 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: 05001-0337

        Category Name: Midi Dresses

        Price: $19.97 $44.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Sale
      • Malia Off Shoulder Ruched Dress

        Special Occasion

        Look captivating in our mesmerizing Malia! She'll hug you in all the right places and show off your figure!  

        Fits & Features

        • Off Shoulder Neckline With Mesh Fold-Over 
        • Unlined, Fitted Long Sleeves 
        • Midi Length Silhouette I Side Slit
        • Mesh Fabric I Knit Lining I Ruching Throughout
        • Curve Hugging Fit I Plenty 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

        Special Occasion products cannot be returned to any retail locations.

        Style Number/Barcode: 05001-0369

        Category Name: Midi Dresses

        Price: $34.97 $64.90

        On Sale: Yes

        Availability: Out of Stock

        Product Badge:
        • Ships Free
      • Off Shoulder Trumpet Hem Midi Dress

        Look trendy and chic to all your holiday outings with this fab off-shoulder dress! 

        Fits & Features

        • Elastic Off Shoulder Neckline I Vertical Seams At The Bust
        • Fitted Long Sleeves
        • Midi Length Silhouette With Trumpet Hem 
        • Ponte Fabric 
        • Curve Hugging Fit I 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: 05101-0416

          Category Name: Midi Dresses

          Price: $9.97 $37.90

          On Sale: Yes

          Availability: Out of Stock

          Product Badge:
          • Clearance
        • Off Shoulder Trumpet Hem Midi Dress

          Look trendy and chic to all your holiday outings with this fab off-shoulder dress! 

          Fits & Features

          • Elastic Off Shoulder Neckline I Vertical Seams At The Bust
          • Fitted Long Sleeves
          • Midi Length Silhouette With Trumpet Hem 
          • Ponte Fabric 
          • Curve Hugging Fit I 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: 05101-0365

            Category Name: Midi Dresses

            Price: $9.97 $37.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Ribbed Off Shoulder Sweater Dress

            We're such softies for soft sweaters. Cuddle up to this cozy and sweet sweater dress!

            Fits & Features

            • Off Shoulder Neckline 
            • Fitted Long Sleeves
            • Midi Length Silhouette
            • Ribbed Knit Fabric
            • Form-Hugging Fit 
            • Ample Stretch

            Style Number/Barcode: 06005-0275

            Category Name: Midi Dresses

            Price: $6.97 $38.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Cowl It's Done Midi Dress

            We're lovin' your style, babe. Show them how it's done in this bold midi 

            Fits & Features

            • Narrow Spaghetti Straps That Cross At The Back
            • Cowl Neckline
            • Midi Length Silhouette
            • Smooth Jersey Knit I Fully Lined
            • 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: 05103-0453

            Category Name: Midi Dresses

            Price: $9.97 $35.90

            On Sale: Yes

            Availability: Out of Stock

            Product Badge:
            • Clearance
          • Serious Sparkle Glitter Midi Dress

            Okay, but this dress?! Now that's some serious sparkle!

            Fits & Features

            • Tank-Inspired Shoulder Straps 
            • Square Neck & Back I Back Zipper With Hook & Eye Closure
            • Midi Length Silhouette I Slit At Center Back 
            • Lurex Knit Fabric 
            • Bodycon Fit I Moderate Stretch

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

              Style Number/Barcode: 05101-0496

              Category Name: Midi Dresses

              Price: $9.97 $36.90

              On Sale: Yes

              Availability: Out of Stock

              Product Badge:
              • Clearance
            • It Girl Cowl Neck Midi Dress

              This dress is made for an "it" girl like yourself!

              Fits & Features

              • Narrow Shoulder Straps That Cross At The Back 
              • Cowl Neckline
              • Midi Length Silhouette
              • Smooth Jersey Knit I Lined 
              • Curve Hugging Fit I Bodycon Fit 
              • 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: 05101-0411

              Category Name: Midi Dresses

              Price: $9.97 $34.90

              On Sale: Yes

              Availability: Out of Stock

              Product Badge:
              • Clearance
            • Annie Bodycon Wrap Satin Midi Formal Dress

              Special Occasion 

              Embrace classy sophistication in the Annie satin midi formal dress designed in a flattering bodycon silhouette with a chic wrap hem.

              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, bust knit lining
              • Square neckline
              • Wide shoulder straps
              • Back zipper and hook-eye closure
              • Bodycon silhouette
              • Wrap midi-length hem
              • Runs true to size

               

              Where to Wear:

              Weddings, dressy celebrations, date night, cocktail soirees, engagement parties, rehearsal dinners

              Style Number/Barcode: 05001-000406

              Category Name: Midi Dresses

              Price: $54.90

              Availability: In Stock

              Available Color: MAUVE

              Available Size: XS, S

            • Classy Lady Satin Midi Dress

              Oh girl! Class and sass are what this midi is all about! 

              Fits & Features

              • Adjustable Spaghetti Straps 
              • Bustier-Style Bodice
              • Zipper With Hook & Eye At The Back
              • Midi Length Silhouette 
              • Satin-Like Fabric I Fully Lined 
              • Bodycon 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: 05103-0438

                Category Name: Midi Dresses

                Price: $9.97 $39.90

                On Sale: Yes

                Availability: Out of Stock

                Product Badge:
                • Clearance
              • In A Ruche Mesh Midi Dress

                A dress you'll want to rush right into! Flaunt and show off your curves in this sexy midi.

                Fits & Features

                • Adjustable Spaghetti Straps 
                • Plunging V Neckline I Square Back
                • Zipper With Hook & Eye Closure At Back 
                • Midi Length Silhouette I Side Slit 
                • Ruching Throughout 
                • Lined, Mesh Fabric
                • Curve Hugging Fit I Moderate Stretch

                  Style Number/Barcode: 05103-0706

                  Category Name: Midi Dresses

                  Price: $9.97 $46.90

                  On Sale: Yes

                  Availability: Out of Stock

                  Product Badge:
                  • Clearance
                • Feline This Leopard Midi Dress

                  Lovin' that look, girl! You're going to be feeling this mini dress as soon as you slip it on! 

                  Fits & Features

                  • Adjustable Spaghetti Straps
                  • Cowl Neckline I Square Back
                  • Zipper With Hook & Eye Closure At Back
                  • Midi Length Silhouette With Front Slit 
                  • Unlined, Satin-Like Fabric I Tonal Leopard Print Throughout 
                  • Relax Fit I Minimal Stretch

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

                  Style Number/Barcode: 05102-0401

                  Category Name: Midi Dresses

                  Price: $9.97 $38.90

                  On Sale: Yes

                  Availability: Out of Stock

                  Product Badge:
                  • Clearance
                • Glitzy Goals Sequin Midi Dress

                  Go on and show 'em that glow! You'll be ringing in the New Year in style with our Glitzy Goals midi dress!

                  Fits & Features

                  • Adjustable, Narrow Spaghetti Straps That Cross At The Back
                  • Plunging V Neckline I Padded Bust 
                  • Midi Length Silhouette
                  • Ribbed Knit Fabric I Iridescent Sequins Throughout 
                  • Bodycon Fit I 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: 05103-0522

                    Category Name: Midi Dresses

                    Price: $9.97 $38.90

                    On Sale: Yes

                    Availability: Out of Stock

                    Product Badge:
                    • Clearance
                  • Knit Girl Mock Neck Sweater Dress

                    When cozy meets chic. This midi is just what you need for that winter wardrobe! 

                    Fits & Features

                    • Mock Neckline 
                    • Fitted Long Sleeves 
                    • Midi Length Silhouette 
                    • Ribbed Knit 
                    • Bodycon Fit I 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: 06005-0569

                      Category Name: Midi Dresses

                      Price: $6.97 $39.90

                      On Sale: Yes

                      Availability: Out of Stock

                      Product Badge:
                      • Clearance
                    • Candace Crepe Midi Dress

                      Special Occasion

                      Up your evening outfit with our stunning Candace! She's the perfect little partner-in-crime for a date night or GNO! 

                      Fits & Features

                      • Adjustable Spaghetti Straps 
                      • Back Zip With Hook & Eye Closure
                      • Sweetheart Neckline With Deep Wire V At Center I Princess Seams
                      • Midi Length Silhouette I Front Slit 
                      • Crepe Fabric
                      • Form-Hugging Fit 

                       

                       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: 05001-0271

                      Category Name: Midi Dresses

                      Price: $29.97 $44.90

                      On Sale: Yes

                      Availability: Out of Stock

                      Product Badge:
                      • Ships Free
                    • Velvet And Mesh Midi Dress

                      Glam up your look with this lovely dress! Her midi-length silhouette, soft floral patterns, and flirty thigh-high slit are a swoon-worthy combo.

                      Fits & Features

                      • Plunging V Neckline
                      • Adjustable Spaghetti Straps With Cross Back Detail & Square Back
                      • Zipper With Hook & Eye Closure At The Side 
                      • Midi Length Silhouette With Thigh High Slit 
                      • Lined, Mesh Fabric With Burnout Velvet Floral Patterns 
                      • Curve 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

                       

                      Special Occasion products cannot be returned to any retail locations.

                      Style Number/Barcode: 05001-0297

                      Category Name: Midi Dresses

                      Price: $19.97 $49.90

                      On Sale: Yes

                      Availability: Out of Stock

                      Product Badge:
                      • Ships Free
                    • Party Animal Leopard Midi Dress

                      Party's here. Stand out and get spotted in this purrrrr-fect dress!

                      Fits & Features

                      • Narrow Spaghetti Straps
                      • Plunging V Neckline I Empire Waist
                      • Zipper With Hook & Eye Closure
                      • Midi Length Silhouette I Small Slit At Center Back
                      • Faux Suede-Like Knit Fabric I Fully Lined
                      • Form Flattering Fit I Moderate Stretch

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

                        Style Number/Barcode: 05103-0705

                        Category Name: Midi Dresses

                        Price: $16.97 $42.90

                        On Sale: Yes

                        Availability: Out of Stock

                        Product Badge:
                        • Clearance
                      • Impressive Beauty Bodycon Midi Dress

                        Get dressed to impress in this bodycon midi dress perfect for brides-to-be or a dressy date night! 

                        Fit & Features

                        • Smooth knit fabric lined with stretchy knit
                        • Square neckline, spaghetti straps
                        • Side ruched seams
                        • Bodycon silhouette
                        • Midi-length hem
                        • Runs true to size

                        Style Number/Barcode: 05101-3933

                        Category Name: Midi Dresses

                        Price: $9.97 $35.90

                        On Sale: Yes

                        Availability: Out of Stock

                        Product Badge:
                        • Ships Free