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.

  • Serving Allure Halter Cowl Neck Midi Dress

    You'll be serving allure at your next happy hour in this curve-flaunting midi dress featuring a plunging cowl neck with a bar strap accent and open back with sleek tie-back straps.

    Fit & Features

    • Smooth knit fabric, high stretch, knit lining
    • Sleeveless plunge cowl neckline, bar strap accent
    • Tie-back halter straps
    • Open back, lower tie-back spaghetti straps
    • Form-hugging fit
    • Midi-length flared hem
    • Runs true to size

    Style Number/Barcode: 05101-000033

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Effortless Mood Ribbed Knit Midi Dress

    Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Open back 
    • Tie-back accent
    • Midi-length, high side slit
    • Lined ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4526

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Jaimie Formal Surplice Wrap Tea Length Dress

    Special Occasion

    Show some curves in the Jaimie Formal Surplice Wrap Tea Length Dress designed to flaunt your hourglass in a form-fitting silhouette. She features puff long sleeves, a surplice v-neckline on a fitted bodice, side ruched seams, and a wrap-style skirt. Composed of sleek knit fabric that offers plenty of stretch. Finish your look in rhinestone hoops and a clutch.

    Fit & Features

    • Surplice v-neckline, puff long sleeves
    • Bra-friendly design
    • Fitted bodice, side ruched seams
    • Wrap-style skirt, form-fitting silhouette
    • Short-length hem
    • Sleek knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05001-1012

    Category Name: Midi Dresses

    Price: $19.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek Trendsetter Halter Midi Dress

    Keep it sleek and stylish in this on-trend midi dress! It features a sleeveless halter neckline with tie-back spaghetti straps, ruching at the bust, and a mid-length, fitted silhouette. Complete the look with a faux leather jacket and clear mules.

    Fit & Features

    • Sleeveless halter neckline
    • Tie-back spaghetti straps
    • Center ruched detailing at the bust
    • Mid-length, fitted silhouette
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1309

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Unforgettable Glam Ruched Midi Dress

    Channel unforgettable glamour with a midi dress that showcases your chic style. The dress features a wrap V-neckline, spaghetti straps, ruching throughout, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with plenty of stretch. Complete the look with a moto jacket and heels.

    Fit & Features

    • Wrap V-neckline
    • Spaghetti straps
    • Ruching
    • Midi-length silhouette
    • Lined smooth knit fabric
    • Form-hugging fit, plenty of stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1341

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Own It Ribbed Knit Midi Dress

    Own your look with a ribbed dress that makes a head-turning impression! The dress features a crew neckline, long sleeves, a sexy cutout at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a teddy jacket.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Cutout at the waist
    • Midi-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1079

    Category Name: Midi Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classy Evening V-Neck Knotted Midi Dress

    You're in for a classy evening in this chic midi dress! It features flowy short sleeves, a V-neck, a front knot accent, and a slit on a bodycon silhouette. The slinky knit fabric offers a moderate stretch. Complete the look in strappy heels. 

    Fit & Features

    • Flowy short sleeves
    • V-neckline
    • Front knot accent
    • Slit midi-length hem
    • Slinky knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1376

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rare Find Satin Ruched Slip Midi Dress

    A satin slip dress as chic and sultry as this is a rare find! It features adjustable spaghetti straps on a ruched v-neckline with a tie keyhole, front high-cut slit, and a midi-length hem. Composed of a luxe satin fabric with minimal stretch. Perfect for styling with sparkly jewelry.

    Fit & Features

    • Adjustable spaghetti straps
    • Ruched bust, v-neckline, tie keyhole
    • Front high-cut slit
    • Midi-length hem
    • Luxe satin fabric, minimal stretch
    • Fits true to size

    Style Number/Barcode: 05101-1325

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curves Ahead Midi Bodycon Dress

    This midi bodycon dress hugs your curves in all the right places! It features a sleeveless, cowl neck bodice with sleek spaghetti straps, a slit accent, and a form-hugging silhouette. Complete the look in lucite mules for a night out.

    Fit & Features

    • Spaghetti straps 
    • Cowl neckline
    • Slit accent
    • Bodycon silhouette
    • Midi length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1563

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Own the Evening Off-The-Shoulder Midi Dress

    When you walk in, the night officially starts. This off-the-shoulder midi dress is all about shaping curves and serving quiet luxury with a bold slit. Perfect for date nights and dressy events!

    Fit & Features

    • Mesh-lined fabric
    • Off-the-shoulder neckline
    • Side slit
    • Ruched bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4162

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M

  • Sound The Alarm Ruched Midi Dress

    Raise the heat in a sexy midi dress for your date night with bae. The midi dress features a sleeveless square neckline, adjustable spaghetti straps, ruching throughout, and a midi-length silhouette. The dress is composed of a lined mesh knit fabric that offers a form hugging fit with a slight stretch. Complete look with mules

    Fit & Features

    • Sleeveless square neckline, padded cups
    • Adjustable spaghetti straps
    • Ruching
    • Midi length silhouette 
    • Lined mesh fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1359

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Only You Floral Midi Dress

    They'll have eyes for only you in this gorgeous floral midi dress. It features a sleeveless V-neckline, spaghetti straps, and a mid-length, curve-hugging fit with an asymmetrical hem. The lightweight stretchy knit fabric showcases an all-over romantic floral print. Style this dress with strappy heels.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Mid-length, form-fitting silhouette, asymmetrical hem
    • Knit fabric, moderate stretch
    • Floral print
    • Runs true to size

    Style Number/Barcode: 05101-1360

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On Me Side Slit Midi Dress

    All eyes on you in this sleek midi dress designed to flaunt your figure! It features a flattering square neck with a draping effect, spaghetti straps, bodycon midi hem with a sultry side slit. Complete the look in sparkly mules.

    Fit & Features

    • Sleeveless spaghetti straps
    • Squareneck with draping effect
    • Bodycon midi hem
    • Side slit
    • Sheen knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1365

    Category Name: Midi Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Astra Formal Satin Corset Midi Dress

    Special Occasion 

    Step out like the one that got away in a formal midi dress that brings the glamour to your special event. Astra features a sleeveless sweetheart neckline, padded cups that allow you to go bra-free, and adjustable spaghetti straps. The bodice features a corset style with flexible boning to achieve that snatched look. The slim-fit waist leads to a midi-length silhouette that is accented with a high side slit on the left. The dress is composed of a satin-like fabric that offers a form hugging fit with minimal stretch. Complete look with rhinestone heels

    Fit & Features

    • Sleeveless sweetheart neckline
    • Padded cups, adjustable spaghetti straps
    • Corset-bodice, flexible boning 
    • Midi length silhouette
    • High side slit
    • Line satin fabric
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05001-0944

    Category Name: Midi Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Look My Way Lace-Up Slinky Knit Dress

    This midi dress is a major head-turner! It features a sleeveless square neck, spaghetti straps, lace-up back detail, and a side slit with ruching to showcase your amazing legs on a midi style hem. Composed of a slinky knit fabric with a moderate stretch. Style with trendy mules for a dinner party.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back
    • Side slit with ruching
    • Bodycon midi hem
    • Slinky knit-lined fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 05101-1326

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Feels Scoop Neck Strappy Midi Dress

    Feeling the floral trend? This sultry floral midi dress is totally for you! It features spaghetti straps with an adjustable tie on the scoop neck, a form-fitting silhouette, and a side slit on the midi hem. Complete the look in simple heels and hoop earrings.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Adjustable tie on the scoop neck
    • Form-fitting silhouette
    • Side slit midi hem
    • Floral pattern
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1371

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Thinking About Knit Cutout Midi Dress

    You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Twist knot accent
    • Dual cutouts at the waist
    • Midi-length silhouette, high side slit
    • Cotton knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4261

    Category Name: Midi Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lillia Formal Cowl Neck Sequin Midi Dress

    Special Occasion 

    Make a stunning entrance with a sparkling formal dress that stands out in the center of the room. Lillia features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross back, and a midi-length silhouette. The dress is composed of a lined mesh fabric adorned with glitzy sequins throughout. Complete the look with an anklet and clutch.

    Fit & Features

    • Sleeveless cowl neckline
    • Adhesive bra recommended
    • Adjustable spaghetti straps, cross-back 
    • Midi-length silhouette
    • Sequin-knit lined fabric
    • Form-hugging fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 05001-0648

    Category Name: Midi Dresses

    Price: $14.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Glamour Rhinestone And Pearl Mesh Midi Dress

    Sparkle with alluring glamour in this mesh midi dress embellished with mini rhinestones and faux pearl accents. The bodycon fit paired with the back slit detail brings the chic and sultry style.

    Fit & Features

    • Sheer mesh fabric with full-length woven lining, moderate stretch
    • Mini rhinestone and faux pearl embellishments
    • Sleeveless sweetheart neckline with padded bust, cowl neck draped overlay
    • Adjustable spaghetti straps, back zipper with hook-eye closure
    • Ruched seams, back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3889

    Category Name: Midi Dresses

    Price: $55.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Shimmering Beauty Glitter Tie-Back Midi Dress

    Show up to the party looking like beauty in this glitter slit midi dress! Featuring a sleeveless, square neck with a low-cut, tie-back, and a bum ruching to accentuate your curves. The knit fabric offers a moderate stretch. Complete your dazzling look with metallic heels. 

    Fit & Features

    • Sleeveless, spaghetti straps
    • Square neck, low-cut back with tie
    • Bum ruching
    • Slit midi-length hem
    • Glitter knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05103-4181

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Frame Long Sleeve Midi Dress

    Bring the sweetness in this long sleeve midi dress featured in a sweetheart neck, bodycon silhouette, and midi-length hem. The dress is composed of a rib-knit fabric offering a moderate stretch. Complete the look with chic booties.

    Fit & Features

    • Long sleeves
    • Sweetheart neckline
    • Bodycon silhouette
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1179

    Category Name: Midi Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Emely Sequin Mesh Double X-Back Midi Formal Dress

    Special Occasion

    You're in for a ravishing night in the Emely sequin mesh formal midi dress for your next evening soiree! She features built-in bust support, a V-neckline, and a figure-flattering bodycon silhouette on the slit midi hem. Keep all eyes on you as you walk away thanks to the open, strappy back design. Complete your look in this midi dress with chic heels and rhinestone earrings.

    Fit & Features

    • Adjustable spaghetti straps
    • Built-in bust support, V-neckline
    • Bodycon fit, slit midi hem
    • Open, strappy back design
    • Zipper closer 
    • Sequin mesh lined-fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05001-0753

    Category Name: Midi Dresses

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feel Sparks Sequin Tube Ruche Dress

    Feel the sparks of shine in this sultry sequin tube midi dress for every party this season! Features a strapless, sweetheart neck with built-in bust support, no-slip grip, all-over ruching detail, and a back zipper with slit accent. The dress is composed of a knit-lined fabric with a moderate stretch. Perfect for styling with platform heels.

    Fit & Features

    • Strapless, sweetheart neck, no-slip grip
    • Built-in bust support, no bra required
    • Ruching detail
    • Midi hem, bodycon fit
    • Back zipper, slit accent
    • Sequin-knit lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1291

    Category Name: Midi Dresses

    Price: $22.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh-So-Chic Floral Velvet Burnout Midi Dress

    Oh-so-chic, this curve-hugging midi dress is designed with lined mesh fabric with a gorg floral velvet burnout pattern. It features a sleeveless cowl neckline, adjustable spaghetti straps to find your customized fit, and a midi-length mermaid silhouette.

    Fit & Features

    • Sheer mesh fabric with knit lining
    • Floral velvet burnout pattern
    • Cowl neckline
    • Adjustable spaghetti straps
    • Back zipper closure
    • Midi-length mermaid silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000042

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: BURGUNDY

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