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.

  • Nia Rhinestone Sleeveless Midi Dress

    Special Occasion

    Light-reflecting rhinestones create a glamorous effect on the Nia formal dress perfect for rehearsal dinners and dressy cocktail parties! She features a sleeveless V-neckline, tank straps, a v-cut back, and a form-hugging midi-length silhouette. The formal dress is composed of a mesh fabric with all-over rhinestone embellishments and a stretchy knit lining. Complete the look with fringe earrings and mules.

    Fit & Features

    • Sleeveless V-neckline, tank straps
    • V-cut back, hidden side zipper and hook-eye closure
    • Form-hugging silhouette, midi-length hem
    • All-over rhinestone embellishments
    • Mesh fabric, stretchy knit lining
    • Strapless bra to sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1468

    Category Name: Midi Dresses

    Price: $19.97 $109.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Kind Of Girl Satin Rhinestone Midi Dress

    For all of the glam kind of girlies! This satin midi dress brings luxe vibes to your night. Featuring a sleeveless square neckline, spaghetti straps, a cutout waist with a rhinestone-embellished bar strap, a flattering bodycon silhouette, and an asymmetrical side slit hem. Complete the look in door knocker earrings for a cocktail party or dressy date night!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps, back zipper closure
    • Cutout waist, rhinestone-embellished bar strap
    • Bodycon silhouette
    • Asymmetrical midi-length hem, side slit
    • Silky satin-knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2291

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweetheart Status Strapless Midi Dress

    This midi dress brings sultry elegance with a sweetheart neckline and a curve-hugging silhouette. Perfect for weddings, cocktail soirees, and date night!

    Fit & Features

    • Smooth knit fabric, lined, moderate stretch
    • Strapless sweetheart neckline, no-slip grip lining
    • Side pleated hip seam
    • Side slit accent
    • Form-hugging fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000149

    Category Name: Midi Dresses

    Price: $40.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: S, M, L, XL

  • Chic Girl Style Turtleneck Midi Dress

    Elevate your fall wardrobe and show off a chic girl style with this bodycon midi dress! It features a sleeveless bodice, a turtleneck, a midi-length hem with a thigh-high side slit, and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a layered chain necklace and ankle booties!

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Midi-length hem
    • High side slit
    • Bodycon silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5096

    Category Name: Midi Dresses

    Price: $17.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Forever Basic Crew Neck Slit Midi Dress

    Forever your basic midi dress with head-turning detail! It features classic cap sleeves, a crew neckline, a flirty cutout back accent, a flattering bodycon silhouette, and a midi-length hem with a high front slit. The soft brushed knit fabric has plenty of stretch. Complete the look with a glam ring set for a family party or casual date!

    Fit & Features

    • Cap sleeves
    • Crew neckline
    • Cutout back accent
    • Bodycon silhouette
    • Midi-length hem, high front slit
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5334

    Category Name: Midi Dresses

    Price: $5.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Color Splash Tie Dye Glitter Midi Dress

    Make a splash this summer in this colorful tie-dye midi dress! It features a sleeveless square neck, adjustable spaghetti straps, side ruched seams that accentuate your curves along the bodycon silhouette, a flirty side slit, and a midi-length hem. The dress is designed with a trendy all-over tie dye print and glitter on mesh fabric with a sewn-in knit lining. Complete the look in heels for an outdoor party!

    Fit & Fetaures

    • Sleeveless square neck, adjustable spaghetti straps
    • Side ruched seams, bodycon silhouette
    • Back zipper and hook-eye closure
    • Side slit, midi-length hem
    • All-over tie-dye print, glitter
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5348

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Looking Lovely Cowl Ruffled Midi Dress

    You'll always look lovely in this sleeveless midi dress at parties and semi-formals! It features a subtle cowl neckline, spaghetti straps with one cascading ruffle trim, a bodycon silhouette, and a flattering asymmetrical ruffled hem on buttery soft knit fabric with a short lining. Complete the look in statement heels.

    Fit & Features

    • Sleeveless subtle cowl neckline
    • Spaghetti straps, one cascading ruffle trim
    • Bodycon silhouette
    • Asymmetrical ruffled midi-length hem
    • Buttery soft knit fabric, short lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2702

    Category Name: Midi Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shimmering Allure Glitter Tube Midi Dress

    This strapless stunner hugs you in all the right places with ruching, glitter mesh, and a leggy side slit made for entrances on date night or dressy events!

    Fit & Features

    • Glitter mesh-lined fabric
    • Strapless tube neckline
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4113

    Category Name: Midi Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: WINE

    Available Size: XS, S

  • Divine Bloom Halter Rosette Flower Midi Dress

    You'll look absolutely divine in this mesh midi dress for a dressy soiree! It features a sleeveless halter cutout neckline with a rosette flower, an elegant sash, ruched side and back seams to accentuate your figure along the bodycon silhouette, and a side slit design. Complete the look with dainty earrings and a bracelet.

    Fit & Features

    • Sleeveless cutout halter neckline
    • Rosette flower and sash
    • Back zipper and hook-eye closure
    • Ruched side and back seams
    • Bodycon silhouette, side slit design, midi-length hem
    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2825

    Category Name: Midi Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Simply Sultry Cutout Bodycon Midi Dress

    This curve-hugging bodycon midi dress is simply sultry and perf for a night out with your girls. It features a sleeveless square neckline, spaghetti straps, alluring waist cutouts at the front and back, ruching down the side seams leading to a midi-length hem, and an all-over bodycon silhouette to show off your figure. The sheer mesh fabric includes a soft knit lining and has plenty of stretch. Style with a layered chain necklace for a hint of glam!

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruched side seams
    • Midi-length hem, bodycon silhouette
    • Sheer mesh fabric, sewn-in knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4648

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty And Sleek Satin Wrap Midi Dress

    Create a cocktail hour look that is pretty and sleek with this silky-satin midi dress! It features a sleeveless V-neckline, spaghetti straps that lead to an open back with a cross-back strappy design, a high waist seam, a wrap-front skirt with pleating at the waist, a high-cut asymmetric midi-length hem, and a bodycon silhouette. The satin-knit fabric has a moderate stretch. Style with lace-up heels and a rhinestone clutch.

    Fit & Features

    • Sleeveless V-neckline, dart seams
    • Spaghetti straps, open back, cross-back strap design
    • High waist seam, wrap-front skirt, pleating
    • High-cut asymmetric midi-length hem
    • Bodycon silhouette
    • Satin-knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2277

    Category Name: Midi Dresses

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Slit Strapless Midi Sweater Dress

    This comfy midi sweater dress is the perfect blend of cozy and cute! It features a trendy strapless straight-across neckline with an elastic banded hem, ensuring a secure and comfortable fit. The high front slit on the midi-length hem adds a flirty touch to your look. Its form-hugging silhouette enhances your natural curves, while the sweater knit fabric with moderate stretch keeps you snug all day. Complete your look with a pair of sandals for a fabulous and playful outfit.

    Fit & Features

    • Strapless straight-across neckline, elasticized hem
    • Midi-length hem
    • High front slit
    • Form-hugging silhouette
    • Sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1708

    Category Name: Midi Dresses

    Price: $3.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bloom Mood Floral Open Back Midi Dress

    Soft, sultry, and ready for sunset dinner and drinks—this floral midi dress brings the heat with a low back and curve-hugging midi silhouette. Just add salty air and a sunset.

    Fit & Features

    • Floral print, mesh-lined fabric
    • Cowl neckline
    • Adjustable spaghetti straps
    • Curve-hugging midi silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000276

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BROWN

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

  • Simple Yet Elevated High Slit Midi Dress

    Simple yet elevated, this high slit midi dress is perfectly chic for your next cocktail party. It features a sleeveless square neckline, thin tank shoulder straps, an empire waist seam along with princess seams, a midi-length hem with a high front slit for a stylish flair, and a slim-fit silhouette. The lined crepe fabric has a moderate stretch. Complete your look with strappy stilettos.

    Fit & Features

    • Sleeveless square neckline, thin tank shoulder straps
    • Empire waist seam, princess seams
    • Back zipper, hook and eye closure
    • Midi-length hem, high front slit
    • Slim-fit silhouette
    • Crepe fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1973

    Category Name: Midi Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Caught In The Midi Crew Neck Tank Dress

    A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!

    Fit & Features

    • Sleeveless crew neck
    • Bodycon silhouette
    • Fitted midi-length hem
    • Stretchy rib knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-5242

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rose So Sweet Halter Cutout Midi Dress

    You'll be sweet as can be in this sleeveless midi dress at dressy birthday dinners or a party! It features a sweetheart neckline, spaghetti straps that crisscross in the back, a bust rose applique, a cutout waist design with rose appliques, a bodycon silhouette, and side slit accent. Complete the look in strappy sandals.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps, criss cross back
    • Bust rose applique
    • Cutout waist design, rose appliques
    • Bodycon silhouette, side slit, midi-length hem
    • Slinky knit fabric, short lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2605

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Be Mine Ditsy Floral A-Line Midi Dress

    Make this ditsy floral midi dress be yours for the summer and beyond! It features a sleeveless V-neckline, adjustable spaghetti straps, a trendy tie-back cutout design, and a flattering A-line silhouette, front slit with a frayed trim, and midi-length hem. Complete the look in block heels for a dressy soiree!

    Fit & Features

    • Sleeveless V-neckline, adjustable spaghetti straps
    • Tie-back cutout design
    • Hidden side zipper closure
    • A-line silhouette, front slit, frayed trim
    • Midi-length hem
    • Ditsy floral print, airy woven fabric, short chiffon lining
    • Runs true to size

    Style Number/Barcode: 05102-5320

    Category Name: Midi Dresses

    Price: $26.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Striking And Chic Marble Print Midi Dress

    So striking and chic, this marble print midi dress will capture all the attention at happy hour! It features a sleeveless V-neckline, spaghetti straps, an asymmetric high-cut midi-length hem creating a thigh-high slit, and a bodycon silhouette that will flaunt your figure. The buttery smooth and stretchy knit fabric features an all-over multicolored marble print pattern. Style with clear mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Asymmetric high-cut midi-length hem, high slit
    • Bodycon silhouette
    • Multi-colored marble print
    • Smooth and stretchy knit fabric, full-length sewn-in knit lining
    • Runs true to size

    Style Number/Barcode: 05102-5231

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Priah Formal Feather One Shoulder Midi Dress

    Special Occasion

    Bring the drama to the evening in the Priah formal sequin dress at banquets or black tie parties! She features a sleeveless one-shoulder neckline with a feathered tank strap, a bodycon silhouette, and a flirty front slit along her midi-length hem. The formal dress is composed of a striking iridescent sequin-knit mesh fabric for the perfect sparkle and a stretchy knit lining. Complete your flawless look with silver rhinestone earrings and bracelet.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Feathered tank strap, back zipper and hook-eye closure
    • Bodycon silhouette
    • Front slit, midi-length hem
    • Iridescent sequin-knit mesh fabric, stretchy knit lining
    • Strapless bra or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1716

    Category Name: Midi Dresses

    Price: $9.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Leave An Impression Abstract Midi Dress

    Leave an impression everywhere you go in this abstract midi dress! It features a sleeveless square neckline, spaghetti straps, side ruched seams to accentuate your curves, and a flattering bodycon silhouette. The dress is designed with a figure-flattering abstract print on knit fabric with a stretchy lining. Complete the look in cute sandals for a lunch date.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Side ruched seams
    • Bodycon silhouette
    • Midi-length hem
    • Abstract print, smooth knit fabric, stretchy lining
    • Runs true to size

    Style Number/Barcode: 05102-5252

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Standout Satin Asymmetric Midi Dress

    You'll be such a chic standout at cocktail hour in this silky-sleek satin midi dress. It features a strapless straight-across neckline, a fitted bodice, and an asymmetric high-cut midi-length hem with a flowy silhouette. The satin woven fabric has minimal stretch. Style with lace-up stiletto heels!

    Fit & Features

    • Strapless straight-across neckline
    • Dart seam accents
    • Asymmetric high-cut midi-length hem
    • Fitted bodice, flowy silhouette
    • Satin woven fabric, knit lining at the bust, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2752

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Always Chic One-Shoulder Midi Dress

    Always chic and sleek, you'll love styling this smooth knit midi dress for weddings, cocktail parties, and fancy date nights. It features a one-shoulder neckline with a bow-trim design and a form-hugging fit with a flirty flared hem.

    Fit & Features

    • Smooth knit fabric with bust lining, high stretch
    • Sleeveless one-shoulder neckline, no-slip strip
    • Bow-trim design
    • Form-hugging silhouette
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000223

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BURGUNDY

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

  • Flirty Attitude Ruffled High Slit Midi Dress

    Captivate them with your flirty attitude in this on-trend ruffled midi dress! Featuring a strapless straight-across neckline, a fitted bodice with ruched side seams, a midi-length hem with dual high-cut side slits, and ruffled trims and accents, this dress is perfect for a summer party. The buttery-smooth knit fabric offers plenty of stretch. Style with a rhinestone choker necklace and lace-up heels.

    Fit & Features

    • Strapless straight-across elasticized neckline
    • Fitted bodice, ruched side seams
    • Midi-length hem
    • Dual high-cut side slits, ruffled trims and accents
    • Flowy silhouette
    • Smooth knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-2577

    Category Name: Midi Dresses

    Price: $25.97 $56.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendsetting Cutie Cable Knit Lace-Up Dress

    Step out as a trendsetting cutie in this cable knit midi dress perfect for daytime strolls! It features a sleeveless square neck, thin shoulder straps that create the lace-up back design, a tie-waist belt, a bodycon silhouette, a side slit, and a midi-length hem. Complete the look in flat sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck, thin shoulder straps
    • Lace-up back design
    • Tie-waist belt
    • Bodycon silhouette
    • Side slit, midi-length hem
    • Cable knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5155

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale