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.

  • Kiara Formal Plunging Midi Dress
    Special Occasion 

    Bring the charm in our lovely Kiara dress! She features an ivory hue, a plunging V neckline, padded cups, princess seam and adjustable narrow straps. Her slim fit bodice features a narrow waist band accent and leads to a flounced midi silhouette skirt with a ruffled hem. Dress is composed of a slightly sheer crepe fabric with a full knit lining and offers a curve hugging fit with a moderate stretch. The back features a lower back zipper closure with a ruched detailing.

    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: 05001-4052

    Category Name: Midi Dresses

    Price: $29.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sydney Formal Taffeta Midi Dress
    Special Occasion 

    Make an unforgettable entrance in our breathtaking Sydney dress! She features a rich navy blue color, an off the shoulder neckline, padded cups and princess seams. Her slim fit bodice leads to a flattering flounce silhouette that brings plenty of flair! Dress is composed of a lined taffeta fabric that offers a relaxed fit with a moderate stretch. Includes a petticoat and back zipper closure.

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

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-4064

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

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

    Impress in dazzling sequins as you make a diva worthy entrance in our Annalynn dress! She features an all over black hue, a straight strapless neckline, a built in no slip strip and a flattering midi length. The all over lined mesh fabric is adorned with gleaming sequins set in a baroque and diamond pattern. Dress offers a form hugging fit with minimal stretch. Includes a back zipper closure with a fish hook clasp.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-3992

    Category Name: Midi Dresses

    Price: $24.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Blossomed Babe Floral Halter Midi Dress

    You'll blossom looking like a babe in this floral chiffon midi dress at every dressy soiree! . The stunning halter neckline features an eye-catching stone insert that draws attention, while the flowy midi-length hem creates a graceful silhouette.

    Fit & Features

    • Floral print, chiffon lined fabric
    • Halter neckline, stone insert, spaghetti strap tie-back closure
    • Flowy midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-4040

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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: 05001-0173

    Category Name: Midi Dresses

    Price: $25.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tonight Is Love Midi Dress

    Love is in the air! And you will feel it tonight in this midi dress!

    Fits & Features 

    • U-Neckline
    • Cap Sleeves
    • Back Slit
    • Back Zipper
    • Unlined Ponte Composition
    • Form Hugging Fit With Moderate Stretch 

     

    Model is 5'7" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05103-1590

    Category Name: Midi Dresses

    Price: $6.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sensational Satin Mini Dress

    Stir the crowds in this sensational little number! This navy blue mini dress features a simple, yet sexy front with spaghetti straps and low rounded neckline, an enticing strappy back, and a seductive form hugging fit. Satin-like knit fabric offers plenty of stretch. Includes a full lining. 

    Style Number/Barcode: 05103-3114

    Category Name: Midi Dresses

    Price: $20.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bennet Lace Trim Satin Midi Dress

    Special Occasion

    Create a gorgeous look in the Bennet midi dress designed with sleek stretch satin fabric and a dainty lace trim at the bust. The front keyhole cutout and high-cut slit add a chic allure to the fitted silhouette.

    Fit & Features

    • Stretch satin fabric, full-length knit lining
    • Sleeveless V-neckline, sheer lace trim, padded bust
    • Keyhole cutout below the bust, high waist seam
    • Adjustable spaghetti straps, back zipper with hook-eye closure
    • Pleating at the waist, high front slit
    • Midi-length fitted silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail parties, fancy date nights, and dinner parties.

    Style Number/Barcode: 05001-2638

    Category Name: Midi Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Suited In Satin Dress

    Get glammed up in this sexy burgundy satin dress! You'll be ready for any close with with a plunging neckline, adjustable shoulder straps, an X back, a hidden back zipper closure and a slim fit. Dress is composed of an unlined satin knit fabric that offers plenty of stretch. 

    Style Number/Barcode: 05101-8379

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Essentials Midi Dress

    Sometimes less is more! This basic midi length can be kept casual or paired with accessories to dress it up! 

    Fits & Features

    • Tank Shoulder Straps
    • Scoop Neckline
    • Midi Length Silhouette
    • Soft Knit Composition I Fully Lined
    • Curve Hugging Fit I Ample Stretch

     

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

    Style Number/Barcode: 05102-3587

    Category Name: Midi Dresses

    Price: $24.90

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Arabella Formal Heat Stone Mesh Dress
    Special Occasion 

    Adorn yourself with plenty of shine in our Arabella burgundy dress! She features a mock neck, unlined fitted long sleeves and a curve hugging midi length silhouette. She is composed of a burgundy hued lined mesh fabric adorned with gold hued heat stones set in a flashy baroque pattern. Dress offers a moderate stretch and includes a back zipper closure.

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-3995

    Category Name: Midi Dresses

    Price: $29.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bold Prints Abstract Floral And Leopard Midi Dress

    The midi dress features a sleeveless cowl neckline, sleek spaghetti straps, an abstract floral pattern, a leopard print, and ruching throughout. Complete outfit with block heels for the ultimate night out!

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless cowl neckline
    • Spaghetti straps
    • Ruching
    • Abstract floral pattern
    • Leopard print
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3909

    Category Name: Midi Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Shine Factor Rhinestone Asymmetrical Midi Dress

    Bring the shine to your event in a midi dress that features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back design, rhinestones, and an asymmetrical high-side slit. 

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless cowl neckline
    • Adjustable spaghetti straps, cross-back design
    • Rhinestones
    • Asymmetrical high-side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3500

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thriving Blooms Corset Floral Slit Midi Dress

    Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace.

    Fit & Features

    • Ditsy floral print, woven fabric
    • Wide shoulder straps, sweetheart neckline
    • Corset bodice
    • Side pockets
    • A-line silhouette, front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4051

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charming Muse Open Back Flocked Velvet Midi Dress

    The midi dress features a sleeveless cowl neckline, adjustable spaghetti straps that cross at the back, a flocked velvet pattern, and a mermaid silhouette. Complete the outfit with clear heels.

    Fit & Features

    • Lined mesh and velvet fabrication
    • Sleeveless cowl neckline
    • Open back design
    • Adjustable spaghetti straps that cross at the back
    • Flocked velvet pattern
    • Midi length hem
    • Mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3849

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flawless Look Flocked Floral Mesh Bodycon Midi Dress

    Showcase a chic flawless look for your next cocktail party in this lined mesh midi dress designed with a velvet flocked floral pattern to turn heads. It features a sleeveless subtle sweetheart neckline with a dainty lace trim, bungee spaghetti straps, a back slit accent, and a bodycon silhouette to hug your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Velvet flocked floral pattern
    • Sweetheart neckline with lace trim
    • Bungee spaghetti straps
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3888

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Feeling Flawless Flocked Floral Mesh Bodycon Midi Dress

    You'll feel flawless and chic in this lined mesh midi dress designed with a velvet flocked floral pattern to get you all the compliments. It features a sleeveless subtle sweetheart neckline with a dainty lace trim, spaghetti straps, a back slit accent, and a midi-length bodycon silhouette to hug your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Velvet flocked floral pattern
    • Sweetheart neckline with lace trim
    • Spaghetti straps
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3890

    Category Name: Midi Dresses

    Price: $20.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunkissed and Snatched Halter Midi Dress

    Serving body, legs, and “where’d you get that?” energy. This halter midi dress hugs every curve in a flattering bodycon fit while the cutouts do all the flirting! Pair with cute sandals or mules.

    Fit & Features

    • Stretchy knit fabric
    • Halter neckline with tie straps
    • Side cutouts
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000022

    Category Name: Midi Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Flawless Look Flocked Floral Mesh Bodycon Midi Dress

    Showcase a chic flawless look for your next cocktail party in this lined mesh midi dress designed with a velvet flocked floral pattern to turn heads. It features a sleeveless subtle sweetheart neckline with a dainty lace trim, spaghetti straps, a back slit accent, and a bodycon silhouette to hug your curves.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Velvet flocked floral pattern
    • Sweetheart neckline with lace trim
    • Spaghetti straps
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3892

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Modern Minimalist Long Sleeve Midi Dress

    Keep it sleek in a smooth knit dress that features a square neckline, fitted long sleeves, and a midi-length hem. Channel those casual vibes when you pair this midi dress with statement sneakers. 

    Fit & Features

    • Smooth knit fabrication
    • Square neckline
    • Fitted long sleeves
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05102-5966

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sparkling Glam Velvet Glitter Halter Midi Dress

    The velvet glitter dress features a sleeveless v-shaped halter neckline, a wrap silhouette, and a midi-length hem. Complete a semi-formal outfit with glitter heels.

    Fit & Features

    • Lined velvet glitter fabrication
    • Sleeveless
    • V-shaped halter neckline
    • Wrap silhouette
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3803

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rhea Long Sleeve Wrap Glitter Midi Dress

    Special Occasion

    The formal glitter knit dress features a plunging v-neckline, long sleeves, ruching to enhance curves, and a wrap midi-length silhouette with a high slit. Complete the formal outfit with a rhinestone clutch. 

    Fit & Features

    • Lined glitter knit fabrication
    • Plunging v-neckline
    • Long sleeves
    • Ruching
    • High-slit
    • Wrap silhouette
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05001-2594

    Category Name: Midi Dresses

    Price: $9.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Silhouette Ruched Knit Midi Dress

    Show off your stunning curves in this sleek midi dress designed with smooth and stretchy knit fabric. It features a sleeveless pleated cowl neckline, spaghetti straps, ruched side and back seams to flaunt your figure, and a midi-length mermaid silhouette.

    Fit & Features

    • Smooth and stretchy knit-lined fabric
    • Cowl neckline with pleating
    • Spaghetti straps
    • Ruched side and back seams
    • Midi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3878

    Category Name: Midi Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sparkly Beauty Glitter Velvet Strapless Midi Dress

    Sparkle up the night with your beauty in this luxe midi dress designed with glitter velvet fabric for the prettiest shine. It features a strapless straight-across neckline with a chic satin-knit fold-over design, pleating at the waist, and a midi-length bodycon silhouette accented with a back slit.

    Fit & Features

    • Glitter velvet fabric with knit lining at the bust, moderate stretch
    • Strapless straight neckline with satin-knit fold-over design
    • Pleated waist
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3731

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale