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.

  • Heart Beat Halter Wrap Midi Dress

    Make his heart skip a beat in this sultry midi dress that flaunts your figure on a sleeveless, halter silhouette with sleek bungee spaghetti straps and a stylish asymmetrical wrap hem. Complete the look in earrings and strappy heels for date night.

    Fit & Features

    • Sleeveless, halter neck
    • Bungee spaghetti straps
    • Bodycon silhouette
    • Asymmetrical wrap midi hem
    • Sleek knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1408

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Fridays Halter Midi Dress

    Bring the heat this summer in this sultry midi dress on a Friday night out! It features an off-the-shoulder, halter neckline, a cinched bust with cutout accents, a form-fitting silhouette, and a flirty side slit. Complete the look in strappy mules.

    Fit & Features

    • Off-the-shoulder, halter neckline
    • Cinched bust, cutout accents
    • Form-fitting silhouette
    • Side slit, midi hem
    • Texture knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4444

    Category Name: Midi Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Stunning Simple Knit Midi Dress

    This simple knit midi dress will create the most stunning looks! The basic must-have features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, a curve-hugging midi-length silhouette, and an alluring high front slit. The smooth knit fabric offers plenty of stretch. Style this dress with sleek hoop earrings and strappy heels.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, lace-up back, tie closure
    • Form-fitting silhouette
    • Midi-length hem, front slit
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1614

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Muse Asymmetrical Midi Dress

    Catch all the glances like the gorgeous muse you are in this printed midi dress! It features a sleeveless V-neckline, adjustable spaghetti straps, a midi-length, asymmetrical hem, a curve-hugging silhouette, and an all-over geometric multi-print pattern. Complete the look with sleek hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Midi-length, asymmetrical hem, ruching down one side
    • Form-fitting silhouette
    • Geometric multi-print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4644

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Palisades Ruched V-Neck Midi Dress

    Let the sun kiss your shoulders in this flowy midi dress! It features a sleeveless ruched v-neck and spaghetti straps that lead to the sultry open-back with a lace-up closure. Complete the look in trendy sandals.

    Fit & Features

    • Sleeveless, ruched v-neck, spaghetti straps
    • Flowy midi-length silhouette
    • Open-back, lace-up closure
    • Gauze woven fabric
    • Inner lining
    • Fits true to size

    Style Number/Barcode: 05102-4456

    Category Name: Midi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Express Yourself O-Ring Bandeau Midi Dress

    Express your stylishly bold self in this midi dress! It features a strapless, bandeau top with a string tie o-ring, cutout bodice, and midi bodycon skirt with a sultry side slit. Composed of ribbed knit fabric with a moderate stretch. Finish the look in oversized sunglasses.

    Fit & Features

    • Strapless bandeau top
    • String tie o-ring, cutout bodice
    • Midi bodycon skirt
    • Side slit 
    • Ribbed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 06005-1263

    Category Name: Midi Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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

    Special Occasion

    Step out in the chic Mabel satin midi dress designed with a lace-up back that turns heads and a front wrap slit for effortless movement. 

    Fit & Features

    • Stretch satin fabric, sewn-in knit lining
    • Scoop neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Front wrap slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Prom, weddings, cocktail parties, date nights, engagement parties, rehearsal dinners, birthdays, dinner parties

    Style Number/Barcode: 05001-2760

    Category Name: Midi Dresses

    Price: $29.97 $54.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY, BLUE

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

    Product Badge:
    • Sale
  • Take Me On A Getaway Midi Dress

    Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline, thin straps that tie at the back of the neck
    • Front ruching, adjustable drawstring
    • Front waist cutout
    • Midi-length, form-fitting silhouette, side slit
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1414

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Passport To Paradise Midi Dress

    The island may be breathtaking but you'll also be a sultry view in this sleeveless midi dress featuring a square neck, spaghetti straps, a cutout bodice, asymmetrical hem, and a side ruched drawstring that lets you customize the fit. Complete the look in a straw floppy hat.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Cutout bodice
    • Side ruched drawstring
    • Form-fitting
    • Asymmetrical midi hem
    • Slinky knit lined fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4620

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet but Sculpted Off Shoulder Midi Dress

    Romantic with a sultry flair? Say less. This off-shoulder midi dress stuns with a sweetheart neckline, curve-hugging bodice, and flared hem that brings the drama to date nights and dressy occasions.

    Fit & Features

    • Smooth knit fabric with subtle sheen, stretchy knit lining
    • Off shoulder sweetheart neckline
    • Mini bust ruched seam
    • Short-sleeve cuffs
    • Form-hugging bodice
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000356

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: DENIM

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

  • Babe Got Back Glitter Midi Dress

    Babe, you've got back! Showcase this sultry glitter midi dress all over town. It features a sleeveless, one-shoulder strap neckline, an open-back with lattice straps, a form-fitting silhouette, a side slit cutout, and a midi hem. Complete the look in a rhinestone bracelet and heels.

    Fit & Features

    • Sleeveless, one-shoulder strap neckline
    • Open-back, lattice straps
    • Form-fitting silhouette
    • Side cutout slit
    • Midi-length hem
    • Glitter knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1572

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Beauty Halter O-Ring Dress

    You'll be a beautiful view on the beach in this halter midi dress featuring a sleeveless, sweetheart neck, a front O-ring atop the cutout bodice that leads to the form-fitting silhouette. Complete the look with a straw purse.

    Fit & Features

    • Sleeveless, sweetheart halter neck
    • Front O-ring
    • Cutout bodice
    • Form-fitting silhouette
    • Midi-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4443

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simple Sleek Silhouette Midi Dress

    Showcase a simple sleek silhouette in this chic satin midi dress. It features a sleeveless cowl neckline, dual spaghetti straps that lead to a strappy lace-up back, and a flowy, midi-length, sheath silhouette. Complete the look with hoop earrings and strappy heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Dual spaghetti straps
    • Open back, strappy lace-up design
    • Flowy, midi-length, sheath silhouette
    • Woven satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1550

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Strappy Moment Midi Dress

    Have yourself a stylish strappy moment in this sleek midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back lace-up design, and a fitted midi-length silhouette with a sultry side slit to showcase some leg. Complete the look with trendy clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Cross-back lace-up strappy design, tie closure
    • Midi-length, curve-hugging fit
    • Side slit
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1395

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Catch A Glance Cutout Midi Dress

    Make heads turn in this bold and alluring midi dress! It features a sleeveless crew neckline, tank shoulder straps, a major cutout at the bust, a center triangle accent, waist cutouts that lead to the back, and a midi-length, curve-hugging silhouette with a chic high side slit. Style this dress with strappy mules for a night out.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Large cutout at the bust
    • Center triangle accent
    • Waist cutouts that lead to the back
    • Midi-length, form-fitting, bodycon silhouette, side slit
    • Double-lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4620

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropic Like It's Hot Halter Midi Dress

    It's vacay season and this halter midi dress is here for it! Featuring a sleeveless, high neckline with a tie closure, cutout bodice with a cinch accent, and a bodycon midi-length hem. Composed of a nylon-blend knit fabric with a moderate stretch. Finish the look with trendy mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, high halter neckline, tie closure
    • Cutout bodice, cinch accent
    • Bodycon silhouette
    • Midi-length hem
    • Nylon-blend knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1305

    Category Name: Midi Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Instant Connection Tube Midi Dress

    Everyone will feel electric love when you walk in wearing this tube midi dress designed with a fabulous bodycon silhouette that flaunts your figure!

    Fit & Features

    • Smooth knit, stretchy fabric
    • Tube strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000123

    Category Name: Midi Dresses

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Sass Off The Shoulder Dress

    Subtle yet sassy, create a sultry allure in this off-the-shoulder midi dress featuring short-sleeve cuffs, twist accent bust, and a ribbed-knit fabric offering a form-hugging fit and a moderate stretch. Complete the look in lucite heels for a summer party.

    Fit & Feature

    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Twist accent bust
    • Form-hugging fit
    • Midi-length hem
    • Ribbed knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4646

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Best Of Me V-Neck Cutout Midi Dress

    Impress the room by showing up in this sultry midi dress perfect for cocktail hour! Featuring a sleeveless, v-neck, adjustable spaghetti straps, and a flirty knot accent with dual waist cutouts that lead to the bodycon silhouette. Complete the look in chic lucite mules.

    Fit & Features

    • Sleeveless, v-neck, adjustable spaghetti straps
    • Back zipper closure
    • Front knot accent, dual waist cutouts
    • Bodycon silhouette
    • Midi-length hem
    • Slinky knit fabric, inner knit lining, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4357

    Category Name: Midi Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • One More Moment Sweater Dress

    Make a lasting impression leaving the pool party in this chic cover-up sweater dress! It features a sleeveless, square neck, spaghetti straps that lead to an open-back with lace-up closure, a form-fitting silhouette, and a side slit atop the midi-length hem. Complete the look in sunglasses.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • Open-back, lace-up closure
    • Form-fitting silhouette
    • Slit midi-length hem
    • Sweater knit fabric, slightly sheer, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1317

    Category Name: Midi Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fall For Floral Chiffon Midi Dress

    Fall for these florals! Bare your shoulders in this sleeveless midi dress featuring a square neckline with non-slip grip lining, adjustable spaghetti straps, a form-fitting silhouette, and a flirty front slit accent. Complete the look in braid strap mules for a birthday brunch.

    Fit & Features

    • Sleeveless, square neckline, non-slip grip lining
    • Adjustable spaghetti straps
    • Back zipper closure, smocked
    • Form-fitting silhouette
    • Front slit accent, midi-length hem
    • Floral chiffon fabric, lining
    • Runs true to size

    Style Number/Barcode: 05101-2249

    Category Name: Midi Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner Party Satin Ruffle Midi Dress

    This satin midi dress will have you looking so lavish and capturing all the attention at a dinner party or cocktail hour! It features a sleek sleeveless square neckline, spaghetti straps, a form-fitting silhouette, and an asymmetric midi-length hem creating a high front slit with a ruffled trim. The luxe satin fabric offers a moderate stretch. Complete the look with an elegant hairpiece for a classy updo.

    Shop Crepe Version: Add Some Flair Ruffle Detail Midi Dress

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, cross-back strap design
    • Form-fitting silhouette
    • Asymmetric midi-length hem
    • Front slit, ruffled trim
    • Satin fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1549

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Island Palms Strappy Midi Dress

    Enter paradise island in this sultry midi dress perfect for a dinner with a view! It features a sleeveless, square neck, spaghetti straps, high waist seam, and a strappy open-back, bodycon silhouette, side ruched seam, and slit along the hem. Complete the look in statement fringe earrings.

    Fit & Features

    • Sleeveless, square neck, spaghetti straps
    • High waist seam, strappy open-back
    • Bodycon silhouette
    • Side ruched seam and slit
    • Midi-length hem
    • Palm print, knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4508

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Wanderer Paisley Cutout Midi Dress

    Embrace the wanderlust life! Look like a babe in this medallion paisley midi dress featuring a sleeveless, v-neck, spaghetti straps, and knot accented bust atop a sultry cutout bodice that leads to the form-fitting midi hem. Complete the look in strappy sandals for a festival.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Knot accented bust
    • Cutout bodice
    • Form-fitting midi hem
    • Medallion paisley print
    • Crepe knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4342

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale