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.

  • Delightful Directions V-Neck Floral Ruffled Midi Dress

    Make a charming impression in this floral midi dress showcasing a flowy ruffled silhouette and lace-up back that turns heads. Perfect for brunch, shower celebrations, and graduations!

    Fit & Features

    • Floral print, chiffon-lined fabric
    • V-neckline, spaghetti straps
    • Lace-up back
    • Flowy ruffled silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3905

    Category Name: Midi Dresses

    Price: $23.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Marianna Ruched Glitter Knit Formal Midi Dress

    Special Occasion

    Show up and stun like the glitzy babe you are in the Marianna ruched glitter knit formal midi dress! Crafted with a glistening glitter knit fabric, all eyes will be on you as you take the dance floor. She features a sleeveless sweetheart neckline with subtle chic draping, adjustable spaghetti straps to find your perfect fit, ruching down the side and back seams to accentuate your gorgeous curves, a thigh-high side slit to add some allure, and a bodycon silhouette. Complete your look with rhinestone heels for all the more sparkle!

    Fit & Features

    • Stretchy glitter knit fabric
    • Draped sweetheart neckline
    • Adjustable spaghetti straps, back zipper closure
    • Ruched side and back seams
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2107

    Category Name: Midi Dresses

    Price: $29.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Can’t Look Away Tube Midi Dress

    Drama in the best way. This tube midi dress hugs your curves with side ruching and turns up the volume with ruffled high slits made for showing off a little leg.

    Fit & Features

    • Soft knit stretchy-lined fabric
    • Tube neckline
    • Side ruched seams
    • Bodycon fit
    • High side slits with ruffled trim detail
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05103-000308

    Category Name: Midi Dresses

    Price: $34.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Good Looks Mock Neck Long Sleeve Knit Midi Dress

    This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!

    Fit & Features

    • Soft and stretchy ribbed knit fabric
    • Mock neckline
    • Fitted long sleeves
    • Form-hugging fit
    • Center back slit
    • Runs true to size

    Style Number/Barcode: 05102-5221

    Category Name: Midi Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Silhouette Abstract Print Mesh Midi Dress

    Showcase a sultry silhouette in this sheer mesh midi dress designed with a multi-colored abstract print for a bold vibe. It features a mock neckline with long fitted sleeves, a bodycon silhouette to hug your curves, and a full-length knit lining with a scoop neckline and spaghetti straps.

    Fit & Features

    • Abstract printed sheer mesh fabric, plenty of stretch
    • Mock neckline
    • Long fitted sleeves
    • Midi-length bodycon fit
    • Full-length knit lining, scoop neckline, adjustable spaghetti straps
    • Runs true to size

    Style Number/Barcode: 05102-5879

    Category Name: Midi Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Admiring Muse Sleeveless Bodycon Floral Midi Dress

    Feel and look effortlessly cute in this watercolor floral mesh midi dress everywhere you go! This sleeveless bodycon dress features adjustable spaghetti straps and a square neckline that accentuates your curves. The ruched bodycon fit flatters your figure while the midi-length hem adds a chic touch. Complete the look in strappy block heels.

    Fit & Features

    • Watercolor floral print, mesh lined fabric, moderate stretch
    • Adjustable spaghetti straps
    • Square neckline
    • Ruched bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3123

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Days Strapless Bodycon Midi Dress

    A trendy babe like you needs this effortless strapless bodycon midi dress for easy styling! 

    Fit & Features

    • Double-lined rib knit stretchy fabric
    • Strapless neckline
    • Bodycon fit
    • Flowy midi-length hem
    • Extra glitter for maximum sparkle - may have some natural fallout
    • Runs true to size

    Style Number/Barcode: 05102-000021

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Babe Ruched Mesh Midi Dress

    Let your look do the talking in this mesh midi dress! With an eye-catching abstract print and adjustable spaghetti straps, this midi dress will show off your style while the bodycon fit and side-ruched seams enhance your curves. Complete the look in trendy mules for an art show downtown!

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Side ruched seams
    • Bodycon silhouette, midi-length hem
    • Abstract print, mesh fabric, sewn-in knit lining
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5508

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Reese Formal Strapless Marabou Glitter Midi Dress

    Special Occasion

    Glam up your evenings with the Reese formal glitter midi dress for Homecoming or formal celebrations! She features a strapless neckline with a fabulous marabou trim, a bodycon silhouette that hugs your curves, and a front slit along her midi-length hem. The formal knee-length dress is composed of a glitter crepe knit fabric offering endless sparkle and moderate stretch. Style the midi dress with platform heels.

    Fit & Features

    • Strapless neckline, marabou trim
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Glitter crepe knit fabric, moderate stretch
    • Sticky or strapless bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1945

    Category Name: Midi Dresses

    Price: $29.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Hourglass Lace-Up Midi Dress

    Sleek, slinky, unforgettable—this knit midi dress stuns with a draped neckline, curve-skimming ruching, and an open lace-up back. The thigh slit is the perfect finishing touch for a head-turning look for date nights, weddings, or celebrations!

    Fit & Features

    • Smooth knit stretch fabric
    • Pleated cowl neckline
    • Adjustable spaghetti straps
    • Lace-up back design
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000395

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: SAGE

    Available Size: XS, L, XL

  • Summer Smiles Floral Puff Sleeve A-Line Midi Dress

    Your new favorite wear-everywhere floral midi dress from lunches to shower celebrations! The V-neck and puff sleeves create a flattering silhouette, while the A-line silhouette flatters every figure.

    Fit & Features

    • Floral print, cotton woven fabric, cotton woven lining
    • Short puff sleeves with ties
    • V-neckline with bust tie
    • Smocked elastic trim waist
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000164

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mingle Sensation Crepe One-Shoulder Midi Dress

    Mix and mingle in this crepe midi dress looking like a chic sensation! The sleeveless dress features a one-shoulder neckline, a form-hugging fit, and an asymmetric midi-length hem creating a flirty high side slit with a ruffle trim. Complete the look in rhinestone heels for a dressy occasion!

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Form-hugging fit
    • Asymmetric midi-length hem
    • Thigh-high side slit, ruffle trim
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2846

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Reign The Night Satin Midi Dress

    Reign the night in this satin midi dress featuring a sleeveless cowl neckline, spaghetti straps, and a form-hugging midi silhouette accented with an asymmetrical high slit.

    With a sleek finish and effortless shine, this dress is pure luxe. Want more? Browse our stunning satin prom dresses or find a celebration-ready style in our party dresses.

    Fit & Features

    • Satin fabric, moderate stretch
    • Cowl neckline
    • Spaghetti straps
    • Form-hugging midi silhouette
    • Asymmetrical high slit for an alluring look
    • Style runs small

    Style Number/Barcode: 05101-1531

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Endless Events Strappy Back Floral Midi Dress

    For the girl who's a socialite, this watercolor floral midi dress will take you from event to event! With its cowl neckline, bungee spaghetti straps, and strappy back, this dress exudes femininity. The bodycon fit and side ruched seams flatter your curves, while the side slit and midi length hem add a touch of allure to the mesh fabric. Complete the look with luxe earrings and heels.

    Fit & Features

    • Watercolor floral print, mesh fabric lined with stretchy knit
    • Bungee spaghetti straps, strappy back
    • Side slit
    • Bodycon fit
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-3198

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Flirt High Slit Bodycon Midi Dress

    Create a flirty chic look for your next cocktail party in this smooth knit midi dress with a sweetheart neckline, high-cut front slit, and bodycon silhouette to flaunt your curves.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless sweetheart neckline, padded bra cups
    • Spaghetti straps
    • Ruched front seam, thigh-high slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000053

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Add Some Flair Ruffle Detail Midi Dress

    Add some flirty flair to your look with this gorgeous ruffle detail midi dress! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back strap design, a sultry ruffled front slit to show some leg, and a midi-length, sleek, curve-hugging silhouette. The dress is composed of a crepe fabric that offers a moderate stretch. Style the look with eye-catching strappy heels for the perfect date night outfit.

    Shop Long Crepe Version: Tiffany Sleeveless High Slit Formal Dress

    Shop Satin Midi Version: Ravishing Ruffles High Slit Midi Dress

    Fit & Features

    • Sleeveless square neckline, spaghetti straps
    • Strapless or adhesive bra recommended
    • Cross-back strap design, front slit, ruffled hem
    • Midi-length silhouette
    • Crepe fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-0885

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Velvet Bloom Flocked Floral Strapless Midi Dress

    Cue the compliments—this velvet flocked floral midi dress was made to steal them. The strapless neckline and bodycon fit serve up effortless glam for nights that call for drama.

    Fit & Features

    • Sheer mesh fabric with knit lining, moderate stretch
    • Velvet flocked floral pattern
    • Strapless sweetheart neckline, no-slip strip, padded bust
    • Ruching
    • Back zipper with hook-eye closure
    • Midi-length bodycon silhouette, back slit
    • Runs true to size

    Style Number/Barcode: 05101-000453

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: WINE

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

  • Picture Perfect V-Neck Smocked A-Line Midi Dress

    You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

    Fit & Features

    • Woven fabric lined with non-stretch woven
    • Tie spaghetti straps
    • V-neckline
    • Stretchy smocked bodice
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3560

    Category Name: Midi Dresses

    Price: $11.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleek And Iconic Satin Bodycon Midi Dress

    Sleek and iconic, this satin-knit midi dress is perfect for a cocktail party or date night! The asymmetric pleating under the bust and at the waist will highlight your curves while the back slit adds some movement to the bodycon silhouette.

    Fit & Features

    • Satin-knit fabric
    • Square neckline, pleating
    • Spaghetti straps
    • Asymmetric pleating under the bust and at waist
    • Back slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3709

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twinkling Night Glitter Midi Dress

    Have yourself a twinkling night in this shimmering glitter midi dress perfect for birthdays or graduations! Featuring a sleeveless cowl neckline, adjustable spaghetti straps, a bodycon silhouette, and an asymmetrical side slit. Complete the look in platform heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Bodycon silhouette
    • Asymmetrical side slit, midi-length hem
    • Glitter fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-2258

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take Me There V-Neck Slit Bodycon Midi Dress

    A perfectly flattering bodycon midi dress for any of your upcoming social plans!

    Fit & Features

    • Stretchy rib knit fabric
    • V-neckline
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2286

    Category Name: Midi Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dance Floor Diva Ruffled High-Low Midi Dress

    Be the center of attention in this midi dress out on the dance floor! The stretchy sleek knit fabric will give off a subtle sheen that will shine in the light beautifully. The mid-length dress is shaped with a sleeveless cowl neckline and spaghetti straps, and features a form-hugging silhouette to showcase your stunning curves with a high-low ruffled hem that adds drama. Complete the look with fringe hoop earrings and heels for a wedding!

    Fit & Features

    • Sleek knit fabric with subtle sheen, moderate stretch
    • Sleeveless cowl neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Ruffled high-low hem
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05101-2898

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Dinner By The Sea Tube Crochet Midi Dress

    You'll be a dreamy view in this crochet tube midi dress, enjoying a dinner by the sea. The form-hugging silhouette showcases your figure while the high side slit adds a daring touch of allure with seashell trim creates a captivating coastal-inspired look.

    Fit & Features

    • Crochet knit fabric, short knit stretchy lining
    • Strapless tube neckline
    • Form-hugging fit
    • High side slit, seashell trim
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000109

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kim Cowl Neck Bodycon Glitter Midi Dress

    Special Occasion

    Prepare to glisten like never before in the Kim glitter midi dress to make a beautiful impression at spring weddings or formal parties! Crafted from sparkling glitter knit fabric, this midi-length dress is designed with a flattering cowl neckline and spaghetti straps. The flattering bodycon silhouette features a front ruched seam and slit to highlight your figure. Perfect for a night out, this dress will make you feel elegant and exclusive! Complete the look with a clutch and heels.

    Fit & Features

    • Glitter fabric lined with stretchy knit
    • Spaghetti straps
    • Front slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2094

    Category Name: Midi Dresses

    Price: $19.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale