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.

  • Love Is In The Air Lace Trumpet Midi Dress

    Love will be in the air with you in this romantic lace midi dress for engagement parties, bridal showers, or rehearsal dinners! The midi dress features a sleeveless sweetheart neckline with a built-in padded bust, spaghetti straps that lead to an open back with a cross-back lace-up strappy design, flexible boning inserts at the bodice to create an alluring corset design, a hip-hugging silhouette, and a midi-length hem with an adorable ruffled trumpet hem. The sheer floral lace fabric includes a full-length knit lining. Style with rhinestone hoops and clear heels.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust
    • Spaghetti straps, open back, cross-back lace-up strappy design, tie closure
    • Flexible boning inserts, corset design, high waist seam
    • Lower back zipper, hook and eye closure
    • Hip-hugging silhouette, midi-length hem, ruffled trumpet hem
    • Sheer floral lace fabric, full-length knit lining, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2334

    Category Name: Midi Dresses

    Price: $9.97 $58.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beautiful Blooms Floral Asymmetric Midi Dress

    Create a stunning summer date look with this beautiful blooming floral midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an adjustable cross-back design, ruching down the side seam, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon silhouette that will hug your curves. The smooth knit fabric features an all-over bold floral print pattern. Style with hoop earrings and strappy mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, adjustable cross-back design
    • Ruched side seam
    • Asymmetric midi-length hem, high side slit
    • Bodycon silhouette
    • Floral print, knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1601

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Perfection Cutout Midi Dress

    This chic cutout midi dress is elevated perfection! It features a sleeveless subtle sweetheart neckline with a knot detail at the center of the bust, an alluring keyhole cutout under the bust, spaghetti straps, a high waist seam to create a figure-flattering look, a midi-length hem with a thigh-high side slit, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Style with a pair of strappy stilettos.

    Fit & Features

    • Sleeveless sweetheart neckline, center knot detail
    • Keyhole cutout under the bust
    • Spaghetti straps
    • High waist seam, midi-length hem, high side slit
    • Bodycon silhouette
    • Ribbed knit fabric, smooth knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5121

    Category Name: Midi Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Passport To Love Crepe A-Line Midi Dress

    Wherever you're headed to celebrate a milestone event, this crepe midi dress is your passport to loving how you'll look on a European getaway! The dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, a padded bust, and a flattering A-line silhouette. Complete the look with fringe earrings.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps
    • Padded bust
    • Back zipper and hook-eye closure
    • A-line silhouette, midi-length 
    • Flowy crepe knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2325

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Strolling The Garden Floral Chiffon Midi Dress

    Stroll the garden looking effortlessly enchanting in this floral chiffon midi dress! It features a sleeveless sweetheart neckline with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a hem slit. Complete the look in strappy sandals for an outdoor wedding.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Bust tie, adjustable spaghetti straps
    • Stretchy smocked back
    • Slit accent, midi-length hem
    • Ditsy floral print, airy chiffon, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2312

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Scene Stealer Halter Bodycon Midi Dress

    Step out like a diva in this halter midi dress to steal the scene! The crisscross back adds a touch of allure, while the bodycon silhouette hugs your curves in all the right places. Pair with chic heels.

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Square halter neckline
    • Crisscross wide shoulder straps
    • Side ruched seams
    • Bodycon silhouette, center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000031

    Category Name: Midi Dresses

    Price: $35.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

  • Paradise Lost Halter Cutout Midi Dress

    Escape to paradise in this halter midi dress that'll make everyone lose their train of thought! It features a sleeveless halter neckline with tie-back straps, a center O-ring insert and cutout bodice, and a flattering bodycon silhouette with a side slit hem. The brushed knit fabric offers plenty of stretch. Complete the look in bold hoop earrings.

    Fit & Features

    • Sleeveless halter neckline, tie-back straps
    • Center O-ring insert, cutout bodice
    • Bodycon silhouette
    • Side slit, midi-length hem 
    • Partially lined brushed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5068

    Category Name: Midi Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spot Me In Leopard Slit Midi Dress

    You can be spotted all season in this leopard print midi dress perfect for a casual lunch or a wine night with friends! It features a sleeveless V-neckline, tank shoulder straps, and a form-hugging, slim silhouette with a flowy slit hem. Complete the look in sleek statement hoop earrings and sandals.

    Fit & Features

    • Sleeveless V-neckline, tank shoulder straps
    • Form-hugging, slim silhouette
    • Front slit
    • Midi-length flowy hem
    • Leopard print
    • Woven non-stretch fabric
    • Runs true to size

    Style Number/Barcode: 05102-4469

    Category Name: Midi Dresses

    Price: $5.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Karlee Formal Ponte Sleeveless Midi Dress

    Special Occasion

    Chat, dance, and toast the night in the perfect Karlee formal midi dress for rehearsal dinners, graduations, or cocktail parties! She features a classic sleeveless V-neckline, wide shoulder straps, a flattering bodycon silhouette, a back slit accent, and a midi-length hem. The formal dress is composed of a smooth ponte knit fabric with a knit lining and moderate stretch. Style with statement earrings and lace-up heels for an eye-catching complete look!

    Fit & Features

    • Sleeveless V-neckline, wide shoulder straps
    • Back zipper closure
    • Bodycon silhouette
    • Back slit accent, midi-length hem
    • Smooth ponte knit fabric, knit lining, moderate stretch
    • Bra friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1746

    Category Name: Midi Dresses

    Price: $29.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Body Talks Crepe Color Block Midi Dress

    Let your body do the talking in this curve-flaunting bodycon midi dress for a night out! It features a sleeveless one-shoulder neckline, dual shoulder straps with a cutout, a pleated side seam, asymmetrical wrap hem, and is designed with a color block pattern. Complete the look with stiletto heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Dual shoulder straps, cutout
    • Pleated side seam, bodycon silhouette
    • Asymmetrical wrap midi-length hem
    • Color block pattern
    • Lined crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4865

    Category Name: Midi Dresses

    Price: $5.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Frolic In Floral Tie Midi Dress

    Frolic all over town in this floral midi dress perfect for an afternoon tea with the girls! It features a sleeveless V-neck, spaghetti straps, a knot tie bust, a curve-hugging silhouette, and a flirty front slit. The dress is designed with a ditsy floral bud print on stretchy knit fabric. Complete the look in trendy wedge sandals.

    Fit & Features

    • Sleeveless V-neck
    • Spaghetti straps
    • Knot tie bust
    • Curve-hugging silhouette
    • Front slit, midi-length hem
    • Ditsy floral bud print, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4865

    Category Name: Midi Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Everyday Slay Ribbed Knit Midi Dress

    Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Open back, double strap design, tie closure
    • Midi-length hem, bodycon silhouette
    • High side slit
    • Ribbed knit fabric, lining at the bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4770

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Sunshine Linen Tie-Back Midi Dress

    For the sun-soaked days ahead, this linen midi dress will make a cute companion! It features a sleeveless square neck, adjustable spaghetti straps, a flirty tie-back closure, and a flowy ruffled hem. Style with trendy sandals and sunglasses.

    Fit & Features

    • Sleeveless square neck
    • Adjustable spaghetti straps
    • Tie-back closure
    • Flowy ruffled midi hem
    • Airy linen fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 05102-5012

    Category Name: Midi Dresses

    Price: $5.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Romance Alert Lace Ruffle High-Low Midi Dress

    Love is in the air and you'll be bringing the romance in this lace midi dress at bridal showers, rehearsal dinners, or graduations! It features a sleeveless V-neckline with a flirty ruffle trim, adjustable spaghetti straps, a form-hugging fit, and a high-low ruffled hem. The dress is composed of a floral lace fabric with a nude stretchy knit lining. Complete the look in rhinestone mules.

    Fit & Features

    • Sleeveless V-neckline, ruffle trim
    • Adjustable spaghetti straps
    • Form-hugging fit
    • High-low ruffled midi-length hem
    • Floral lace fabric, nude stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2284

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cut To The Chase Strapless Cutout Midi Dress

    A little cutout never hurt anybody. This strapless midi hugs your curves with a sleek silhouette and underbust cutout made to turn heads at every RSVP.

    Fit & Features

    • Stretch knit fabric
    • Bodycon silhouette
    • Sweetheart strapless neckline
    • Twist-front bodice with an underbust cutout
    • Midi length
    • Runs true to size

    Style Number/Barcode: 05101-000275

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BLACK

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

  • Still The One Rose Print Chiffon High Low Dress

    Make every heart pitter-patter in this chiffon dress for a dressy celebration or garden party! It features a sleeveless V-neckline, adjustable spaghetti straps, a romantic lace-back design with a lower cutout, and a flowy high-low hem. The dress is composed of an airy chiffon with a garden rose print and a stretch knit lining. Style with platform heels for a chic look!

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Lace-back design, lower cutout
    • Back zipper and hook-eye closure
    • Flowy high-low hem
    • Garden rose print, airy chiffon, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2251

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Can I Have Your Attention Cutout Midi Dress

    Stand out and have all eyes on you in this attention-grabbing midi dress! The alluring style features a sleeveless square neckline, spaghetti straps, a trendy waist cutout, an asymmetric midi-length hem with ruching and an adjustable drawstring, a high side slit, and a curve-hugging silhouette. The stretchy knit fabric showcases an eye-catching sheen. Style with clear heels.

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Waist cutout
    • Asymmetric midi-length hem, ruching, adjustable drawstring
    • High side slit
    • Curve-hugging fit
    • Stretchy knit fabric, lining at the bust
    • Runs true to size

    Style Number/Barcode: 05101-2092

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elegant Era Cowl Neck Midi Dress

    Step into your elegant era looking stunning in this midi dress at rehearsal dinners, graduations, or dressy birthdays! The dress features a sleeveless cowl neckline, spaghetti straps, a form-hugging fit, and a skin-baring front slit. Complete the look in rhinestone platform heels for a touch of luxe!

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Form-hugging fit
    • Front slit, midi-length hem
    • Smooth knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2352

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe Alert Ruched Bodycon Midi Dress

    Sound the alarm in this alluring bodycon midi dress! It features a sleeveless sweetheart neckline with a built-in padded bust and a twist-front design, a small keyhole cutout under the bust, spaghetti straps, ruching down the midi-length silhouette, an asymmetric hem creating a high side slit, and a curve-hugging fit. The smooth knit fabric offers plenty of stretch. Style with platform heels for your next night out.

    Fit & Features

    • Sleeveless sweetheart neckline, padded bust, twist-front design
    • Small keyhole cutout under the bust
    • Adjustable spaghetti straps, back zipper, hook and eye closure
    • Ruching down the midi-length silhouette
    • Asymmetric hem, high side slit, bodycon fit
    • Smooth knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05103-4827

    Category Name: Midi Dresses

    Price: $5.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Charm Swiss Dot Chiffon Midi Dress

    Unlock your sweet charm in this chiffon midi dress perfect for bridal showers, graduation parties, and more! It features a sleeveless V-neck with a twisted bust, adjustable spaghetti straps, a flirty tie-back design, and a flowy silhouette and ruffled hem. The dress is composed of an airy chiffon fabric with a swiss dot pattern and a smooth woven lining. Complete the look in faux pearl heels.

    Fit & Features

    • Sleeveless V-neck, twisted bust
    • Adjustable spaghetti straps
    • Tie-back design
    • Flowy silhouette, ruffled midi-length hem
    • Airy chiffon fabric, swiss dot pattern, smooth woven lining
    • No stretch
    • Runs true to size

    Style Number/Barcode: 05102-5047

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Admiration Satin Floral Midi Dress

    Everyone will look your way with major admiration! Flaunt your florals in this satin midi dress featuring a classy sleeveless cowl neckline, adjustable spaghetti straps, and a slim curve-hugging silhouette. Style with flower earrings and a sleek choker to complete the look.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Slim, curve-hugging silhouette
    • Midi-length hem
    • Floral rose print, silky satin, no stretch
    • Runs true to size

    Style Number/Barcode: 05101-2343

    Category Name: Midi Dresses

    Price: $5.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Room To Grow Floral Cutout Midi Dress

    You'll flourish this season in this fresh floral midi dress perfect for outdoor parties, family gatherings, and baby showers! The dress features adorable puff short sleeves, a sweetheart neck, a ruched bust seam with a cutout accent, a stretchy smocked back, and a flowy midi-length hem with a flirty side slit. Complete the look in platform wedges.

    Fit & Features

    • Puff short sleeves
    • Sweetheart neck
    • Ruched bust seam, stretchy smocked back
    • Cutout accent
    • Flowy midi-length hem, side slit
    • Floral print, airy woven fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2358

    Category Name: Midi Dresses

    Price: $5.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Fine Hour Cowl Neck Slit Mini Dress

    Make the clock strike fine when you stroll in wearing this sultry midi dress to the cocktail party! Featuring a sleeveless cowl neckline, spaghetti straps, a form-hugging silhouette, and a side slit accent. The smooth knit fabric offers plenty of stretch. Complete the look with hoop earrings and heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Side slit accent
    • Midi-length hem
    • Stretchy knit fabric, lined bust
    • Runs true to size

    Style Number/Barcode: 05101-2260

    Category Name: Midi Dresses

    Price: $19.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Denise Satin Bodycon Slit Midi Formal Dress

    Special Occasion

    Sculpted for your most glamorous nights, the Denise satin midi dress pairs a softly draped cowl neckline with a curve-hugging silhouette. A thigh-high slit and open back detail make it the ultimate entrance-making piece.

    Fit & Features

    • Stretch satin fabric
    • Cowl sweetheart neckline
    • Wide shoulder straps
    • Back zipper closure
    • Bodycon silhouette
    • Front wrap slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, bridal celebrations, rehearsal dinners, engagement parties and photoshoots, black tie galas, birthdays, fancy brunches, date nights, milestone celebrations, holidays

    Style Number/Barcode: 05001-000358

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: BROWN, IVORY

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