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.

  • Murphy Long Sleeve Corset Midi Dress

    Special Occasion

    Sophisticated and chic, the Murphy formal midi dress is a perfect choice for a wedding guest outfit! She features a square neckline, a corset-designed bodice with flexible boning to provide structure, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit to show off some leg. The crepe fabric offers a moderate stretch. Style with strappy heels and a sleek clutch.

    Fit & Features

    • Square neckline, corset-designed bodice, flexible boning
    • Bra-friendly design
    • Long fitted sleeves, back zipper, hook and eye closure
    • High waist seam
    • Midi-length hem, high front slit
    • Fitted bodycon silhouette
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-1243

    Category Name: Midi Dresses

    Price: $19.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy Love Mock Neck Midi Dress

    This midi dress is what dreams are made of! It features a cozy brushed rib-knit fabric designed with a mock neck, fitted long sleeves, and a bodycon silhouette. The knit fabric offers a moderate stretch. Style with a crop denim jacket to complete the look!

    Fit & Features

    • Mock neck
    • Fitted long sleeves
    • Bodycon silhouette
    • Midi-length hem
    • Super soft brushed rib-knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-5035

    Category Name: Midi Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Jewel Rhinestone Strap Midi Dress

    The shining jewel of your dress collection! Bedazzle everyone in this sultry midi dress featuring a sleeveless one-shoulder neckline, a dual rhinestone trim strap, a ruched side seam that accentuates your curves, a bodycon silhouette, and an asymmetrical slit hem. Style with a cuff bracelet and heels to complete the look!

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Dual rhinestone trim strap
    • Ruched side seam
    • Bodycon silhouette
    • Asymmetrical slit midi hem
    • Smooth knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-2075

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Winter Chic Off-The-Shoulder Sweater Dress

    This adorable ribbed knit sweater dress will give you a chic look for the winter season! It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, a midi-length, curve-hugging silhouette, and a high front slit. The knit fabric offers a moderate stretch for comfortable wear. Style with knee-high boots.

    Fit & Features

    • Off-the-shoulder neckline, fold-over design
    • Long fitted sleeves
    • Midi-length hem, fitted bodycon silhouette
    • High front slit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1578

    Category Name: Midi Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tessa Formal Crepe Slit Midi Dress

    Special Occasion

    Sophisticated and stunning, celebrate in the Tessa formal crepe midi dress that brings class to every holiday dinner or banquet! She features an off-the-shoulder sweetheart neckline with a sheer mesh insert, a pleated bust with padding and flexible boning, and short-sleeve cuffs. Her form-hugging silhouette accentuates your curves and offers a peek of skin in the front slit along the midi-length hem. The formal dress is composed of a stretch-crepe fabric with lining and minimal stretch. Complete your dressy look in statement heels and a clutch.

    Fit & Features

    • Off-the-shoulder sweetheart neckline, short-sleeve cuffs
    • Pleated bust, padding, flexible boning
    • Back zipper and hook-eye closure
    • Form-hugging, front slit
    • Midi-length hem
    • Crepe fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05001-1220

    Category Name: Midi Dresses

    Price: $14.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Morning Brew Henley Midi Dress

    Serve major looks in the morning slaying it in this midi dress featuring long sleeves, a collared v-neckline, a button-down front, a bodycon silhouette, and a slit hem. Style with a Panama hat and booties!

    Fit & Features

    • Long sleeves
    • Collared v-neckline
    • Button-down front
    • Bodycon silhouette
    • Midi-length slit hem
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4797

    Category Name: Midi Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tilda Formal Velvet Midi Dress

    Special Occasion

     Put your curves on display in the gorgeous Tilda formal velvet dress destined to be your plus one for a wedding or banquet! She features a sleeveless surplice v-neckline, spaghetti straps, a form-hugging silhouette, and a faux wrap midi-length hem with a slit. The formal dress is composed of luxuriously soft velvet fabric with a bust lining and plenty of stretch. Style with fringe earrings and heels to complete the look!

    Fit & Features

    • Sleeveless surplice v-neckline, bust lining
    • Spaghetti straps
    • Form-hugging, front slit
    • Faux wrap midi-length hem
    • Luxe velvet fabric, moderate stretch
    • Strapless or sticky bra recommended
    • Fits true to size

    Style Number/Barcode: 05001-1234

    Category Name: Midi Dresses

    Price: $14.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's Bold And Sleek Halter Slit Midi Dress

    Bold, sleek, and just the right amount of risky. This bodycon midi dress hugs in all the right places with sheer mesh and a daring plunge that does the flirting for you at cocktail soirees or date night!

    Fit & Features

    • Stretch woven fabric, sewn-in knit lining
    • Halter plunge neckline, hardware insert
    • Sheer mesh panels along the bust
    • Back zipper and hook-eye closure
    • Front slit
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000670

    Category Name: Midi Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: WINE

    Available Size: S, M, L

  • Rhonda Formal Velvet Midi Dress

    Special Occasion

    Turn heads in the glamorous Rhonda formal velvet dress for your next holiday party or celebration! She stuns in a sleeveless V-neckline, spaghetti straps, padded cups, and side ruched seams to accentuate your curves along her form-fitting, midi-length hem. The formal dress is composed of luxurious velvet fabric. Complete your dressy look in lattice cutout booties and earrings!

    Fit & Features

    • Sleeveless V-neckline, spaghetti straps
    • Padded cups
    • Side ruched seams
    • Form-fitting silhouette
    • Midi-length hem
    • Velvet fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-1235

    Category Name: Midi Dresses

    Price: $54.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Twist It Up Sweater Midi Dress

    Spice up your everyday look with this sweater midi dress that brings eye-catching detail! It features long sleeves, a v-neck, a twisted bust and cutout, a side slit, and a form-hugging silhouette. Complete the look in a crop denim jacket for lunch!

    Fit & Features

    • Long sleeves
    • V-neck
    • Twisted bust and cutout
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1517

    Category Name: Midi Dresses

    Price: $16.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • You're The One Tie-Front Midi Dress

    This rib knit midi dress will be the one you'll adore for casual outings and more! The dress features long sleeves, a surplice v-neckline, a faux wrap bust atop a flirty cutout bodice with a tie-front closure, and a bodycon silhouette. Style with faux suede booties for the perf autumn look!

    Fit & Features

    • Long sleeves
    • Surplice v-neckline
    • Faux wrap bust
    • Cutout bodice, tie-front closure
    • Bodycon, midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4843

    Category Name: Midi Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Scoop Neck Midi Dress

    You'll be wearing this midi dress on repeat! It features long sleeves, a scoop neck, and a bodycon silhouette with a sultry side slit. The dress is composed of a stretchy rib-knit fabric. Style with pointed-toe booties to complete your cute look!

    Fit & Features

    • Long sleeves
    • Scoop neck
    • Bodycon silhouette
    • Side slit
    • Midi-length hem
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4846

    Category Name: Midi Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lilly Formal Crepe Cutout Dress

    Special Occasion

    Slip into the Lilly formal crepe dress perfect for dressing up on date nights and cocktail soirees! She features a one-shoulder neckline with a single long sleeve, shoulder pad, a cutout waist, and a side slit to flaunt some skin. The formal dress is composed of a stretch-knit crepe-lined fabric that hugs your body like a glove! Complete the look with a glitter clutch and heels.

    Fit & Features

    • One-shoulder neckline, single long sleeve, shoulder pad
    • Cutout waist and side slit
    • Form-hugging silhouette
    • Midi-length hem
    • Lined crepe fabric, moderate stretch
    • Strapless or adhesive bra recommended
    • Fits true to size

    Style Number/Barcode: 05001-1264

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Taste For Glitter Velvet Midi Dress

    You've come to the right midi dress to fulfill your desire to shine! This sleeveless glitter velvet dress features a cowl neckline, spaghetti straps, and a curve-hugging design. Complete the look in strappy stiletto heels for a wine & dine type of night!

    Fit & Features

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Curve-hugging silhouette
    • Midi-length hem
    • Glitter velvet knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1889

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Elevated Glamour Glitter Knit Midi Dress

    Show off an elevated glam style in this gorgeous glitter knit midi dress. It features a sleeveless V-neckline with a wrap-front design, spaghetti straps, front ruching leading to a high front slit, and a midi-length, curve-hugging silhouette. The glitter knit fabric offers a moderate stretch. Complete the look with rhinestone heels.

    Fit & Features

    • Sleeveless V-neckline, wrap-front design
    • Spaghetti straps
    • High waist seam
    • Front ruching, front slit
    • Midi-length hem, form-hugging fit
    • Glitter knit fabric, knit lining at the bust, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05101-1856

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chelsea Satin Midi Formal Dress

    Special Occasion

    Striking in its simplicity, the Chelsea formal dress brings sleek confidence to any dress-up moment. Crafted in glossy satin with a form-hugging silhouette and side slit, this midi is made for the spotlight—with a square neckline that feels timeless yet fresh.

    Fit & Features

    • Stretch satin fabric, stretchy knit lining
    • Square neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, bridal showers, receptions, photoshoots, cocktail soirees, birthdays, date nights, anniversaries, dinner parties, formal events

    Style Number/Barcode: 05001-000391

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: RED, IVORY

    Available Size: XS, S, M

  • Craving Shine Glitter Midi Dress

    Indulge yourself with this sparkling glitter midi dress to make a striking impression at cocktail parties! It features a sleeveless scoop neck, spaghetti straps that lead to a cross-back lace-up design, and a form-hugging silhouette with a sultry front slit. The glitzy glitter knit fabric offers a moderate stretch. Complete the look with earrings.

    Fit & Features

    • Sleeveless scoop neck, padded cups
    • Adjustable spaghetti straps
    • Lace-up back, tie closure
    • Lower back zipper
    • Form-hugging silhouette
    • Front slit, midi-length hem
    • Textured glitter knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-1767

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Debby Formal Crepe Mesh Midi Dress

    Special Occasion

    Step out and be seen in the Debby formal midi dress to create an elegant entrance at birthday dinners and art galas! She features an off-the-shoulder neckline, sheer long fitted sleeves with ruched detailing, a form-hugging silhouette, and a sultry side slit to showcase some skin. The formal dress is composed of a crepe fabrication that offers moderate stretch. Complete the look in simple stiletto heels.

    Fit & Features

    • Off-the-shoulder neckline
    • Sheer long fitted sleeves, ruched detailing
    • Form-hugging silhouette
    • Side slit, midi-length hem
    • Crepe fabrication, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1343

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Madi Formal Crepe Slit Midi Dress

    Special Occasion

    A closet staple for your upcoming weddings or dressy events, the Madi formal midi dress evokes a clean and pristine allure so you'll always feel classy! She features an off-the-shoulder, sweetheart neckline, foldover short-sleeve cuffs, and a form-hugging silhouette with a front side ruched seam atop a sultry side slit along her midi-length hem. The formal dress is composed of a stretch-knit crepe fabric that hugs your body like a glove! Complete the look with twisted rhinestone earrings.

    Fit & Features

    • Off-the-shoulder, sweetheart neckline
    • Foldover short sleeve cuffs
    • Form-hugging silhouette
    • Front side ruched seam, side slit
    • Midi-length hem
    • Crepe fabric, lining at the bust, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1580

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Alluring Trendsetter Halter Midi Dress

    Show off your alluring trendy style in this sleek curve-hugging midi dress! It features a cross-front halter neckline with tie-back straps, a cold-shoulder design with long fitted sleeves, and a midi-length asymmetric hem creating a chic high side slit. The smooth knit fabric includes a full lining. Complete the look with your fave mules.

    Fit & Features

    • Cross-front halter neckline, tie-back straps
    • Cold-shoulder design
    • Long fitted sleeves
    • Midi-length asymmetric hem, high side slit
    • Form-hugging silhouette
    • Knit fabric, full lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4904

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Doesn't Get Better Knit Midi Dress

    It doesn't get better than having this knit midi dress in your rotation! The dress features a trendy one-shoulder crew neckline with a long sleeve, spaghetti strap, and cutout bust that leads to the form-hugging silhouette with a sultry side slit hem. Complete the look in chic marabou heels.

    Fit & Features 

    • One-shoulder crew neckline
    • Long sleeve, spaghetti strap
    • Cutout bust
    • Form-hugging silhouette
    • Side slit hem, midi-length 
    • Smooth knit double-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4850

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • A Little Glitz And Glamour Rhinestone Trim Midi Dress

    Show off a little glitz and glamour in this alluring midi dress! It features a sleeveless one-shoulder neckline with an iridescent rhinestone trim strap, a bold front cutout at the waist, a midi-length hem with a faux wrap design, and a curve-hugging silhouette. The crepe fabric offers a moderate stretch. Style with rhinestone hoops and clear heels.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Iridescent rhinestone trim strap, removable
    • Waist cutout
    • Midi-length hem, faux wrap design
    • Fitted bodycon silhouette
    • Crepe fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-4780

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On A Roll Turtleneck Midi Dress

    The styling possibilities are endless with this turtleneck midi dress! It features long sleeves, a bodycon silhouette, and a sultry side slit on stretchy rib-knit fabric. Complete the look in suede booties for the perf autumn outfit!

    Fit & Features

    • Long sleeves
    • Turtleneck
    • Bodycon silhouette
    • Side slit
    • Midi-length 
    • Rib-knit, lined, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4855

    Category Name: Midi Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Head-Turning Chic Marble Print Midi Dress

    Make heads turn in this eye-catching chic bodycon midi dress! It features a sleeveless square neckline, spaghetti straps, bold front and back waist cutouts, ruched detailing down the side seams, and a midi-length, curve-hugging silhouette. The stretchy knit fabric features an all-over abstract marble print pattern for a trendy vibe. Complete the look with clear heels.

     Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Front and back waist cutouts
    • Ruching down the side seams
    • Midi-length hem, fitted bodycon silhouette
    • Abstract marble print pattern
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4837

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale