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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.

  • Effortless Grace Chiffon Midi Dress

    The dress that never tries too hard—but always delivers. This chiffon halter midi flows with every step, featuring a plunging neckline, open back, and A-line skirt that moves effortlessly from the reception to the dance floor.

    Fit & Features

    • Airy chiffon-lined fabric
    • Halter V-neckline, tie closure, back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000644

    Category Name: Midi Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: L

    Product Badge:
    • Best Seller
  • Enchanted Hour Mermaid Midi Dress

    Soft meets sultry in this dreamy mesh midi. Designed with a flocked floral velvet pattern, a mermaid silhouette, and a flared midi hem, it’s your go-to for elegant soirees and dressy date nights!

    Fit & Features

    • Flocked floral velvet pattern, mesh-lined fabric
    • V-neckline
    • Spaghetti straps
    • Mermaid silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000712

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: XS, S, M, L

  • Camila Satin Midi Formal Dress

    Special Occasion

    Built to flatter every curve, the Camila formal dress moves like liquid light. Crafted from glossy satin with a sweetheart neckline and side-pleated seam, this form-hugging midi steals the spotlight with its draped wrap slit—made for those moments when all eyes are on you.

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining, moderate stretch
    • Sweetheart neckline, padded bra cups
    • Spaghetti straps
    • Side pleated seam, front wrap slit
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail soirees, formal celebrations, rehearsal dinners, engagement parties, date nights, shower celebrations, fancy brunches

    Style Number/Barcode: 05001-000562

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: PINK, SAGE

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

  • Barely Blushing Velvet Mesh Midi Dress

    A little romantic, a little rebellious—this mesh midi is made to flirt. The floral velvet flocking and open back bring the drama, while the curve-hugging fit keeps things effortlessly chic for any event.

    Fit & Features

    • Flocked floral velvet, mesh-lined fabric, moderate stretch
    • Scoop neckline
    • Adjustable spaghetti straps
    • open bar back with hook closure
    • Form-hugging fit
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000161

    Category Name: Midi Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: XS, S, M, L

  • Velvet Dream One Shoulder Midi Dress

    Elegance with a little edge. This one-shoulder velvet midi dress features a soft curve-hugging fit, knotted trim detail, and a subtle trumpet hem that moves beautifully with every step—made for holiday soirées and cocktail nights alike.

    Fit & Features

    • Soft velvet-lined fabric
    • One-shoulder neckline with knotted accent
    • Curve-hugging silhouette
    • Trumpet flared midi-length hem 
    • Runs true to size

    Style Number/Barcode: 05101-000772

    Category Name: Midi Dresses

    Price: $40.90

    Availability: In Stock

    Available Color: HUNTER

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

  • Soft Bloom Floral Mesh Midi Tube Dress

    Flirty, fitted, and just the right amount of romantic. This floral mesh midi tube dress hugs every curve with an effortless allure that speaks for itself.

    Fit & Features

    • Sheer mesh fabric, knit lining, high stretch
    • Large floral print
    • Strapless sweetheart neckline
    • All-over ruching
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000681

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BROWN

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

  • Twist the Plot Bodycon Midi Dress

    A little sheer, a little sculpted—this mesh off-shoulder midi is your new statement staple. With its asymmetrical neckline and ruched detailing, it hugs every curve while keeping things effortlessly elevated.

    Fit & Features

    • Mesh fabric lined with stretch knit
    • Asymmetrical off-the-shoulder neckline
    • Ruched side seams
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000410

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

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

  • Camilla Satin Cutout Slit Midi Formal Dress

    Special Occasion

    Designed to catch the light—and their attention—the Camilla formal dress pairs a lustrous satin finish with a sultry waist cutout and draped cowl neckline. The midi silhouette and thigh-high slit strike the perfect balance between effortless allure and timeless polish.

    Fit & Features

    • Stretch satin fabric
    • Cowl neckline
    • Adjustable spaghetti straps
    • Cutout bodice, front slit
    • Form-hugging silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Cocktail parties, weddings, date nights, birthdays, holiday celebrations, fashion events, art gallery openings, formal brunches, rehearsal dinners, luxury lounges

    Style Number/Barcode: 05001-000450

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S

  • Marilee Satin Open Back Midi Formal Dress

    Special Occasion

    Sophisticated with a sultry edge, the Marilee formal dress turns heads with its sleek satin finish and sculpted fit. Designed with double straps, a thigh-high slit, and a tie-back detail, it’s that effortlessly elegant piece that moves with confidence and shine.

    Fit & Features

    • Stretch satin fabric
    • V-neckline
    • Dual spaghetti straps
    • Open tie-back design
    • Pleated bodice
    • Front slit
    • Form-hugging, midi-length silhouette
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail parties, date nights, engagement celebrations, birthdays, fashion events, holiday soirees, dressy events

    Style Number/Barcode: 05001-000354

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: MOCHA, BLACK

    Available Size: XS, S, M, L

  • Floral Whispers Off-The-Shoulder Midi Dress

    A floral moment worth remembering. This off-shoulder midi dress flatters with a ruched body, draped sleeves, and a side slit that shows just enough—perfect for weddings, date nights, and every romantic plan in between.

    Fit & Features

    • Floral print, smooth knit stretch fabric
    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Front slit design
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000732

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: HUNTER

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

  • Romance Language Floral Lace-Up Midi Dress

    Soft texture, bold romance. This floral flocked velvet midi dress stuns with a sweetheart neckline, curve-hugging fit, and lace-up back that adds the perfect touch of drama to dressy occasions and events!

    Fit & Features

    • Flocked floral velvet pattern, mesh-lined fabric with stretch
    • Sweetheart neckline, padded bra cups
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000639

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: WINE

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

  • Twist Of Noir Velvet Midi Dress

    Classic with a sultry twist. This flocked velvet strapless midi features a ruched sweetheart neckline and front slit for an elegant yet daring finish that’s made to turn heads.

    Fit & Features

    • Flocked velvet fabric with stretch
    • Strapless neckline with twisted bust detail
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000716

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XXS, XS, S, L

    Product Badge:
    • Best Seller
  • Glow With It Rhinestone Mesh Midi Dress

    Delicate, dreamy, and just the right amount of shimmer. This rhinestone mesh midi hugs your curves with ruched detailing and a sleek square neckline, catching the light (and attention) from every angle—perfect for cocktail nights, birthdays, or that glam “no special reason” moment.

    Fit & Features

    • Rhinestone-embellishments, mesh-lined fabric, moderate stretch
    • Square neckline
    • Adjustable spaghetti straps
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000004

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

  • Sweetly Sculpted Floral Mesh Midi Dress

    A dress that knows how to flirt back—soft mesh, blooming prints, and a cowl neckline that moves with a little drama. The wrap detail and curve-hugging skirt follow your shape just right, making this your go-to for nights when you want a look that feels effortless yet unforgettable.

    Fit & Features

    • Floral print, mesh-lined fabric, moderate stretch
    • Cowl neckline, padded bra cups
    • Spaghetti straps
    • Wrap cinched bodice accent
    • Curve-hugging silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000770

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Enchanted Noir Lace Up Midi Dress

    A dreamy blend of structure and softness, this strapless midi dress features flocked florals, a sculpted sweetheart neckline, and a lace-up back that adjusts to your perfect fit. The trumpet hem adds that subtle drama, giving every step a little movie-moment movement.

    Fit & Features

    • Flocked velvet, mesh-lined stretchy fabric
    • Strapless sweetheart neckline, padded bra cups
    • Lace-up back, zipper and hook-eye closure
    • Bodycon fit, flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000635

    Category Name: Midi Dresses

    Price: $56.90

    Availability: In Stock

    Available Color: BLACK

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

  • Emme Flocked Velvet Midi Formal Dress

    Special Occasion

    Soft florals meet sculpted elegance in the Emme flocked mesh midi dress, designed with a square neckline and wide tank straps for a clean, modern feel. The side slit adds just the right amount of drama, while the pleated detailing shapes everything beautifully.

    Fit & Features

    • Flocked mesh fabric, lined
    • Square neckline with adjustable tank straps, padded bra cups
    • Back zipper and hook-eye closure
    • Side slit detail
    • Pleated bodycon silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, gala dinners, formal celebrations, holiday parties, cocktail soirees, birthdays, anniversaries

    Style Number/Barcode: 05001-000575

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, WINE

    Available Size: XS, S, L

    Product Badge:
    • Best Seller
  • Crushworthy Mesh Ruched Midi Dress

    Made for evenings that call for a little drama, this mesh midi dress blends a soft cowl neckline with a delicate back slit for just the right dose of romance. The ruched fit sculpts beautifully, while the midi length keeps it sleek and elevated.

    Fit & Features

    • Mesh overlay fabric with smooth knit lining
    • Cowl neckline
    • Adjustable spaghetti straps
    • Ruching throughout the bodice
    • Bodycon silhouette
    • Back slit at hem, midi-length
    • Runs true to size

    Style Number/Barcode: 05101-000591

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: WINE

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

  • Defined And Divine Mesh Midi Dress

    This is that dress you reach for when you want quiet confidence… with a little edge. The wired V-neckline shapes everything just right, while the double tank straps give it that effortless, modern lift. Allover ruching smooths, contours, and moves with you—zero fuss, all polish.

    Fit & Features

    • Mesh overlay fabric with smooth knit lining
    • Sweetheart neckline with V-wire structure
    • Tank-style straps
    • Ruching throughout the bodice and skirt
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000584

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: BLACK

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

  • Brenda Velvet Cutout Midi Formal Dress

    Special Occasion

    Designed for those slow-motion, all-eyes-up moments, the Brenda formal dress glows in luxe velvet with a sculpted bodycon fit that traces every curve. The cowl sweetheart neckline, front slit, and cutout twist back create an effortlessly refined silhouette that delivers chic drama from every angle.

    Fit & Features

    • Soft stretch velvet fabric lined with knit
    • Cowl neckline with tank-style straps, padded bra cups
    • Back cutout detail at the back with twist-knot design
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, galas, formal celebrations, holiday parties, New Year's Eve, cocktail soirees, birthday dinners, fashion-forward events, art gallery openings, formal receptions, red-carpet occasions

    Style Number/Barcode: 05001-000585

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, NAVY

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

  • Petal Imprint Floral Bodycon Midi Dress

    This is the dress you reach for when you want to look effortlessly magnetic. The flocked floral velvet melts over your curves, while the crisscross open back brings the kind of quiet confidence that doesn’t need an intro.

    Fit & Features

    • Stretch velvet with flocked floral detailing
    • Tank-style bodice with V neckline
    • Crisscross strap design with open back
    • Bodycon silhouette with midi length
    • Runs true to size

    Style Number/Barcode: 05101-000708

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BROWN

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

  • Emelia Satin High Slit Midi Dress

    Special Occasion

    Designed for the nights that call for a little extra allure, the Emelia satin midi dress glides with a sleek, sculpted silhouette and a bold high slit designed to turn heads. The lace-up back adds an irresistible touch of drama that elevates the entire silhouette.

    Fit & Features

    • Satin-knit fabric with knit lining, high stretch
    • Sleeveless pleated cowl neckline, padded bust
    • Tank-like shoulder straps
    • Open lace-up back design with tie closure, lower back zipper with hook-eye closure
    • Ruching, high-cut front slit
    • Midi-length hem, form-hugging silhouette
    • Runs true to size

     

    Where to Wear:

    Cocktail parties, dressed-up dinners, formal date nights, wedding guests, bridesmaids, and winter formals.

    Style Number/Barcode: 05001-000539

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: NAVY, HUNTER

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

  • Sweet Chic Flocked Floral Off-The-Shoulder Midi Dress

    This midi dress serves that effortlessly chic confidence the second you slip it on. The off-the-shoulder drape and flocked floral velvet bring a soft, sultry vibe that feels perfect for every dressed-up moment.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Flocked velvet floral pattern
    • Sweetheart neckline, no-slip strip, padded bust
    • Off-the-shoulder short sleeve cuffs
    • Ruching, back zipper with hook-eye closure, back slit
    • Midi-length hem, bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000751

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: BROWN

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

  • Chic Attitude Ribbed Knit Off-The-Shoulder Midi Dress

    A sleek off-the-shoulder midi dress with just the right dose of attitude. The ribbed knit snatches softly, the cutout adds that chic twist, and the midi length keeps the whole look effortlessly elevated.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Off-the-shoulder sweetheart neckline, no-slip strip, center hardware accent
    • Keyhole cutout below the bust
    • Long fitted sleeves
    • High-cut front slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000222

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S, M, L

    Product Badge:
    • Best Seller
  • Majorly Chic Ribbed Knit Mock Neck Midi Dress

    Meet the midi dress that makes minimal feel major. The mock neck and keyhole detail bring a chic vibe, while the ribbed knit stretch keeps it comfy enough from brunch meet-ups to dinner dates.

    Fit & Features

    • Ribbed hacci knit fabric with knit lining, high stretch
    • Sleeveless mock neckline
    • Keyhole cutout at the bust
    • Angled seams under the bust
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000422

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L