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.

  • Can't Deny It One-Shoulder Bodycon Midi Dress

    No one can deny your sultriness in this one-shoulder midi dress perfect for cocktail parties or receptions! The dress is crafted from a smooth double-lined knit fabric with plenty of stretch. It features a one-shoulder neckline, a figure-flaunting bodycon fit, and an asymmetrical midi-length hem.

    Fit & Features

    • Smooth double-lined knit fabric, moderate stretch
    • One-shoulder neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3566

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK, BROWN, RED, WHITE

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

  • Cozy Allure Long Sleeve Slit Midi Dress

    Your new go-to for looking polished without even trying. This hacci rib knit midi dress serves up a body-skimming fit, cozy texture, and a side slit for just the right amount of edge. Perfect for everything from PSL runs to dinners downtown.

    Fit & Features

    • Soft hacci rib knit stretch fabric
    • Sweetheart neckline
    • Fitted long sleeves
    • Side slit accent
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000301

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: IVORY, BLACK

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

  • Kassidy Glitter Cutout Midi Dress

    Special Occasion

    Designed to dazzle with every step, the Kassidy delivers sleek glamour through a glittered knit, bodycon fit, and sculpting cutout bodice. The draped cowl neckline and daring side slit bring soft edge to this scene-stealing midi.

    Fit & Features

    • Glitter knit fabric,knit lining, moderate stretch
    • Cowl neck, padded bra cups
    • Adjustable paghetti straps
    • Cutout bodice
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Homecoming, weddings, engagement parties, birthdays, date nights, dinner parties, cocktail soirees, red carpet events, award shows

    Style Number/Barcode: 05001-000362

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: WHITE, HUNTER, BLACK, RED

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

  • Effortless Flirt Tube Ruffled Midi Dress

    It’s giving effortless flirt. This tube midi dress hugs your curves and brings drama to the hem—aka your go-to for date nights or semi-formal occasions!

    Fit & Features

    • Smooth knit fabric, bust lining, moderate stretch
    • Tube neckline
    • Form-hugging silhouette
    • Ruffled midi hem
    • Runs true to size

    Style Number/Barcode: 05101-000326

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BROWN

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

  • Serve Style High Slit Bodycon Midi Dress

    Serving style with every step, this high slit bodycon midi dress is made for double-takes. The sleek fit and sultry side slit bring effortless chic vibes to any night out.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Sleeveless square neckline, pleated cowl neck overlay
    • Spaghetti straps
    • Ruching
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000604

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S, M, L

  • RSVP Ready Halter Midi Dress

    This halter midi bodycon dress is sleek, sculpted, and made to own the room. Perfect for date nights, rooftop hotel bars, or dressy celebrations!

    Fit & Features

    • Smooth knit stretch fabric
    • Halter sweetheart neckline, tie closure
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000605

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BLACK

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

  • Sensational Delight Sweetheart Cutout Midi Dress

    Create a sensational look in this effortlessly chic midi dress on your next weekend getaway. The small cutout below the bust adds a touch of allure to the flowy A-line silhouette.

    Fit & Features

    • Cotton blend fabric lined with stretchy knit
    • Sweetheart neckline, cutout below the bust
    • Adjustable spaghetti straps
    • Back zipper with hook-eye closure
    • High waist seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5649

    Category Name: Midi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Heavenly Cute Scoop Neck Chiffon Ruffled Midi Dress

    Inspire a heavenly cuteness in this chiffon ruffled midi dress perfect for showers or celebration parties! Crafted from an airy chiffon fabric showcasing a unique burnout pattern, this midi dress offers a flattering scoop neckline adorned with adjustable spaghetti straps and a flowy ruffled silhouette. Complete the look with chic heeled sandals and earrings.

    Fit & Features

    • Chiffon fabric, burnout pattern, stretchy knit lining
    • Scoop neckline, adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Flowy midi-length silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3250

    Category Name: Midi Dresses

    Price: $24.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Currently In Paradise V-Neck Tropical Midi Dress

    This tropical midi dress will be with you paradise for a stylishly chic vacation! Featuring a V-neckline adorned with spaghetti straps and a tie-back design, it's the perfect form-hugging dress for any island adventure. With a side slit and midi-length hem, you'll be sure to turn heads! Complete the look in wedge sandals and earrings.

    Fit & Features

    • Tropical print, stretchy knit fabric, sewn-in knit lining
    • Spaghetti straps
    • V-Neckline
    • Tie-back design
    • Side slit
    • Form-hugging
    • Runs true to size

    Style Number/Barcode: 05102-5633

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stunning Destiny Asymmetrical Slit Bodycon Midi Dress

    It's your destiny to look this stunning in this mesh bodycon midi dress on nights out! With its flattering sweetheart neckline, halter spaghetti straps, and bodycon silhouette, this midi dress is designed to show off your curves. And the striking asymmetrical side slit and elegant mesh fabric add an alluring touch. Complete the look in rhinestone strap heels.

    Fit & Features

    • Mesh fabric, sewn-in knit lining, moderate stretch
    • Halter spaghetti straps
    • Built-in padded underwire bust
    • Asymmetrical side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05103-5486

    Category Name: Midi Dresses

    Price: $21.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leaving An Impression Striped Ribbed Knit Midi Dress

    Leave an impression in this striped knit midi dress everywhere you go! With adjustable spaghetti straps, a sweetheart neckline, a cutout bust, and a form-hugging fit, this dress is both stylish and comfortable. The dual side slits add a trendy flair to the midi-length hem. The ribbed knit fabric offers plenty of stretch. Complete the look in sandals and sunglasses!

    Fit & Features

    • Striped pattern, stretchy ribbed knit fabric
    • Adjustable spaghetti straps
    • Sweetheart neckline
    • Cutout bust
    • Form-hugging fit
    • Dual side slits
    • Runs true to size

    Style Number/Barcode: 06005-1976

    Category Name: Midi Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gretchen Sweetheart Tie Floral Chiffon Midi Dress

    Special Occasion

    From garden parties to bridal showers, the Gretchen floral chiffon midi dress will be the perfect pick for any formal occasion! The delicate tie straps and sweetheart neckline with non-slip grip lining add a touch of elegance. The padded bra cups and ruched bodice provide a flawless A-line silhouette, making it perfect for any occasion. The ruffled midi-length hem flows beautifully into the floral-printed chiffon fabric. Complete the look in stiletto heels.

    Fit & Features

    • Floral printed chiffon fabric, stretchy knit lining with tulle trim
    • Padded bra cups, back zipper and hook-eye closure
    • Tie straps, sweetheart neckline
    • Ruffled hem
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05001-2077

    Category Name: Midi Dresses

    Price: $29.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delightfully Chic Ruffled Floral Chiffon Midi Dress

    Create a delightfully chic outfit for weekend parties in this airy floral chiffon midi dress! Designed with a lightweight sheer chiffon fabric with a lining for coverage, this mid-length dress is accented with a blooming rose print in subtle hues for a simply gorgeous look. It features a square neckline, adjustable spaghetti straps with dainty ruffled accents, a fitted high waist, and a flowy A-line silhouette detailed with a high front slit and feminine ruffled hem. Complete the look with hoop earrings.

    Fit & Features

    • Rose-printed chiffon fabric, stretchy knit lining
    • Square neckline
    • Adjustable spaghetti straps with ruffled accents
    • High waist, back zipper with hook-eye closure
    • A-line fit
    • Front slit, ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3046

    Category Name: Midi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ophelia Satin Lace-Up Midi Formal Dress

    Special Occasion

    The Ophelia formal dress catches every eye with its glossy satin finish and sculpting bodycon fit. The lace-up back detail adds just the right touch of drama—elegant, unexpected, and ready for every RSVP on your calendar.

    Fit & Features

    • Stretch satin fabric
    • V-neckline, spaghetti straps
    • Lace-up open back
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, formal dances, rehearsal dinners, engagement parties, black tie gala and benefit, dinner parties, date night, bachelorettes, birthdays, milestone celebrations, red carpet events

    Style Number/Barcode: 05001-000357

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: DENIM, WINE

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

  • Perfectly Poised Pleated Open Back Satin Midi Dress

    Feel perfectly poised for any occasion in this satin midi dress! Featuring a sweetheart neckline and adjustable straps, this dress accentuates your curves in a flattering silhouette. The pleated bust with a bow and open back adds a touch of elegance, making it ideal for cocktail parties or rehearsal dinners! Complete the look in stiletto heels.

    Fit & Features

    • Satin woven fabric, no stretch
    • Adjustable spaghetti straps
    • Pleated bust
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3456

    Category Name: Midi Dresses

    Price: $22.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fabulous Icon Sleeveless Ribbed Knit Midi Dress

    An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.

    Fit & Features

    • Soft, stretchy ribbed knit fabric
    • Square neckline
    • Underbust seam
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-1853

    Category Name: Midi Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curve Views V-Neck Ruffled Crepe Midi Dress

    This crepe midi dress flaunts your curves from every angle! Perfect for Valentine's, rehearsal dinners, or parties this V-Neck midi dress features a bodycon silhouette to accentuate your curves like an hourglass and a flirty asymmetrical ruffle trim while the front slit adds a touch of chic. Pair this luxe crepe midi dress with fringe earrings, a bracelet, and sleek stiletto heels for a flawless evening look!

    Fit & Features

    • Crepe fabric with stretch
    • Spaghetti straps
    • Asymmetrical ruffle trim
    • Front slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3260

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Is Merry Velvet Glitter Midi Dress

    All is merry and bright with you in this velvet glitter midi dress! Perfect for the holidays, this midi-length dress features a cowl neckline, spaghetti straps, a form-hugging silhouette, and a flirty front slit. Complete the look in strappy block heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Glitter velvet fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2895

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Spring Fling High Slit Ditsy Floral Knit Midi Dress

    Embrace your flirtatious side in this adorable floral knit midi dress! The lightweight stretchy knit fabric is detailed with the cutest ditsy floral print pattern for the spring season. The mid-length dress features a crew neckline, short sleeves, a small back keyhole cutout, a large lower back cutout to add some allure, a high-cut front slit, and a bodycon silhouette to flaunt your curves. Style with hoop earrings and a charm necklace.

    Fit & Features

    • Stretchy knit fabric
    • Ditsy floral print
    • Crew neckline, short sleeves
    • Back keyhole cutout, lower back cutout
    • High front slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5653

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • RSVP To Cute Ditsy Wildflower Tie A-Line Midi Dress

    RSVP yes to shower or birthday invites when you have this cute ditsy wildflower tie A-line midi dress in your closet! Embellished with a ditsy wildflower print, this midi-length dress is sure to turn heads. With short puff sleeves and a square neckline, this dress is perfect for casual-dressy occasions. The tie front bust adds a touch of whimsy while the a-line silhouette and front slit provide movement and a flattering look. Complete the look with luxe earrings and tennis shoes.

    Fit & Features

    • Ditsy wildflower print
    • Woven fabric lined with stretchy knit
    • Tie front bust, back zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3008

    Category Name: Midi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweetest Allure Strapless Floral Eyelet Knit Midi Dress

    Give off the sweetest allure this summer season in this floral eyelet knit midi dress! The stretchy sheer eyelet knit fabric is detailed with an adorable ditsy floral print and includes a full knit lining for coverage. The mid-length dress features a strapless straight-across elasticized neckline and a bodycon silhouette to highlight your gorgeous figure. Style with espadrille wedges for weekend brunch!

    Fit & Features

    • Stretchy sheer eyelet knit fabric, full knit lining
    • Ditsy floral print
    • Strapless straight elasticized neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5488

    Category Name: Midi Dresses

    Price: $5.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Best Behavior Sleeveless Midi Dress

    Classy yet sultry, this sleeveless midi dress is designed to hug your curves in a form-hugging silhouette while the flared hem gives a touch of flirtiness. Perfect for weddings or date nights!

    Fit & Features

    • Smooth knit, stretchy fabric
    • Square neckline
    • Spaghetti straps
    • Side pleated hip seam
    • Form-hugging silhouette
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000036

    Category Name: Midi Dresses

    Price: $36.90

    Availability: In Stock

    Available Color: HUNTER, RED, BROWN

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

  • Dreamy Escape Strapless Tropical Midi Dress

    Serve chic looks on your dreamy escape in this tropical print midi dress. The stretchy lined knit fabric showcases a detailed tropical print pattern on the figure-flaunting silhouette. The bodice features a strapless elasticized straight-across neckline, leading to a bodycon fit with a mid-length hem. Style with combat booties to add some edge!

    Fit & Features

    • Stretchy knit fabric with knit lining
    • Tropical print
    • Strapless elasticized straight neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5539

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Arielle Bow Strap A-Line Midi Formal Dress

    Special Occasion

    Let the compliments flow when you're in the Arielle bow strap A-line midi formal dress looking effortlessly blissful as a bridesmaid, wedding guest, or attending a graduation! She features a sweetheart neckline, tulle bow shoulder straps, and a ruched bodice, this dress will make you feel like a princess. The A-line silhouette and ruffled midi-length hem add a whimsical touch, while the swiss dot tulle woven fabric adds an extra level of sophistication. Complete the look in patent stiletto heels and earrings.

    Fit & Features

    • Swiss dot tulle woven fabric lined with stretchy knit
    • Bow shoulder straps, padded bra cups
    • Back zipper hook-eye closure
    • A-Line silhouette
    • Ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05001-2043

    Category Name: Midi Dresses

    Price: $49.97 $99.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free