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.

  • Tropical Mood Strapless Midi Dress

    This tropical midi dress will have you looking like a warm weather cutie on vacation or a weekend escape!

    Fit & Features

    • Tropical print, knit fabric with stretchy knit lining
    • Strapless neckline
    • Form-hugging bodice
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000014

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Special Something Off-The-Shoulder Floral Midi Dress

    Look iconic all season long in this off-the-shoulder floral midi dress as a gorgeous wedding guest or attending a garden party! 

    Fit & Features

    • Floral print, smooth knit stretchy fabric
    • Off-the-shoulder neckline
    • Short-sleeve cuffs
    • Bodycon silhouette
    • Flared midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000030

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunny Daze Charm Halter V-Neck Floral A-Line Midi Dress

    This sun-ready halter floral midi dress will have you dreaming of chic garden parties and outdoor soirees! Designed to flatter, this midi dress boasts a drop waist seam to accentuate your waistline and a classic A-line silhouette perfect for pairing with kitten heels.

    Fit & Features

    • Floral print, eyelet fabric, woven lining
    • Halter V-neckline, tie closure
    • Drop waist seam detailing
    • A-line silhouette, back zipper and hook-eye closure
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4050

    Category Name: Midi Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty Day Corset Floral Midi Dress With Pockets

    Sun drenched days call for this pretty floral midi dress boasting a gorgeous corset top and hidden side pockets for keeping your hands warm! Perfect for graduations, brunch, and shower celebrations.

    Fit & Features

    • Floral print, woven fabric, woven lining
    • Sweetheart neckline, bust tie, underwire bust
    • Wide shoulder straps, side zipper and hook-eye closure
    • Lace-up back
    • Corset bodice, hidden side pockets
    • A-line silhouette, slit midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4052

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Total Attraction Cutout Bodycon Midi Dress

    Look and feel like a babe in this bodycon midi dress with a flirty cutout twist back design and side slit for effortless movement! Pair with cute sandals.

    Fit & Features

    • Texture knit fabric, stretchy knit lining
    • Scoop neckline, spaghetti straps
    • Twist cutout back design
    • Side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2281

    Category Name: Midi Dresses

    Price: $42.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Spring Fling Corset Tie A-Line Midi Dress

    Unleash your inner romantic in this midi dress at showers, graduations, or brunch! The tie bust corset bodice and lace-up back create a flattering silhouette, while the midi-length hem and textured fabric add a touch of playfulness.

    Fit & Features

    • Texture woven fabric, woven lining
    • Sweetheart neckline, wide shoulder straps
    • Dual tie front corset bodice, lace-up back
    • Back zipper and hook-eye closure
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6068

    Category Name: Midi Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Breeze By Strapless Striped A-Line Midi Dress

    Breeze by like a breath of fresh air in this striped midi dress! It's adorned with hidden side pockets to keep your hands warm and has a flattering A-line silhouette.

    Fit & Features

    • Striped print, woven fabric, woven lining
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6069

    Category Name: Midi Dresses

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Toasty Sweetheart V-Neck Bodycon Knit Midi Dress

    This sleeveless ribbed knit midi dress features a striking V-neckline and bodycon fit with a front slit detail for movement. Perfect for layering with a jacket and heels.

    Fit & Features

    • Stretchy ribbed knit fabric
    • V-neckline
    • Spaghetti straps
    • Front slit
    • Midi-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-2221

    Category Name: Midi Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Special Something Floral Bodycon Midi Dress

    Experience effortless elegance in this floral midi dress for dressy occasions! The strapless neckline accentuates your shoulders while the bodycon silhouette flatters your curves.

    Fit & Features

    • Floral print, mesh-lined fabric, moderate stretch
    • Strapless neckline
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-4120

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Beauty V-Neck Slit Midi Dress

    Jet set on your next tropical getaway or weekend escape in this perfect slit midi dress! Featuring a bold metal insert and a flattering bodycon fit, this dress is perfect for any occasion. 

    Fit & Features

    • Palm leaf tropical print, stretchy knit fabric, soft knit lining
    • V-neckline with metal insert
    • Spaghetti straps
    • Side slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6095

    Category Name: Midi Dresses

    Price: $19.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Island Breeze Tropical Slit Midi Dress

    Turn heads on vacay in this tropical midi dress perfect for sunset cocktails and dinner! Featuring a strapless neckline with insert, this form-hugging dress will flatter your curves and keep you cool with a side slit and midi hem.

    Fit & Features

    • Tropical palm print, stretchy knit fabric, short knit lining
    • Strapless neckline with insert
    • Form-hugging fit
    • Side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-6088

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Weekend Chic Sleeveless Midi Dress

    Elevate your weekend look with this sleeveless midi dress with a sleek boat neckline, flirty low-cut back, and a flattering flowy silhouette. Dress it up with strappy sandals!

    Fit & Features

    • Woven fabric
    • Boat neckline
    • Low-cut back
    • Drop waist seam
    • Flowy silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000164

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Drama Strapless Asymmetric Knit Midi Dress

    This chic strapless asymmetric midi dress will bring the sultry drama to your night-out vibe. Designed with a stretchy knit fabric, this mid-length dress features a strapless straight-across neckline with a cowl-draped design for that stylish flair. The fitted bodice is supported with flexible boning inserts, followed by a high waist seam. The ruching down the side seam will accentuate your gorgeous curves on the bodycon silhouette. The asymmetric hem creates a high side slit for a touch of allure. Complete your look with lace-up stilettos!

    Fit & Features

    • Stretchy knit fabric, lined bust
    • Strapless straight neckline with cowl-draped design
    • Flexible boning
    • High waist seam, ruched side seam
    • Asymmetric hem, high-cut side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05101-3205

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, BERRY

    Available Size: XS, S, M

    Product Badge:
    • Sale
  • Muse Mode Abstract Print Midi Tube Dress

    Giving art gallery energy but make it flirty. This abstract print midi tube dress is stretchy, lined, and made to turn sidewalks into runways—perfect for girls’ night, date night, or that “just because” moment.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Abstract print
    • Strapless straight-across neckline
    • Midi-length hem
    • Fitted silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000404

    Category Name: Midi Dresses

    Price: $45.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pure Perfection Satin Wrap Dress

    Look and feel like pure perfection in this classy satin midi dress for cocktail hour and semi-formal occasions! It features a sleek sleeveless cowl neck, spaghetti straps, a high waist seam, a form-fitting silhouette, and side pleating along the faux-wrap midi skirt. Complete the look with rhinestone heels.

    Fit & Features

    • Sleeveless cowl neck, spaghetti straps
    • High waist seam
    • Form-fitting silhouette
    • Side pleating, faux-wrap midi skirt
    • Silky satin fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-1600

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Delightful Charm Halter A-Line Midi Dress

    Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!

    Fit & Features

    • Woven fabric, no stretch
    • Halter pleated neckline
    • Open back, zipper and hook-eye closure
    • Beaded tie waist
    • A-Line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5648

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Harriet Formal Satin Corset Midi Dress

    Special Occasion

    Be radiant in the fiery Harriet formal satin midi dress perfect for bridesmaids, rehearsal dinners, or banquets! She features a figure-snatching corset-designed bodice with a square neckline, adjustable spaghetti straps, and flexible boning inserts. A side pleated seam leads to the bodycon silhouette showcasing a high front wrap slit along the midi-length hem. The formal dress is crafted from a glossy and sleek satin fabric that exudes sophistication! Complete the look with earrings and block heels.

    Fit & Features

    • Sleeveless square neckline, adjustable spaghetti straps
    • Corset-designed bodice, flexible boning
    • Bodycon silhouette, high front wrap slit, midi-length hem
    • Satin knit fabric, moderate stretch
    • Pasties or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-2557

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: RED

    Available Size: XS, S

    Product Badge:
    • Sale
  • Seona Formal Satin Midi Dress

    Special Occasion 

    Radiate elegance in a formal dress that showcases your timeless style! Seona features a pleated cowl neckline, spaghetti straps, a cutout at the midriff, and a midi-length silhouette accented with a high side slit. The dress is composed of a silky-satin fabric that offers a form-hugging fit with a moderate stretch. Complete the look with rhinestone heels and a clutch.

    With a smooth, luminous finish, this dress was made to shine. Keep the luxe look going with breathtaking satin prom dresses or go for a sophisticated statement with our wedding guest dresses.

    Fit & Features

    • Sleeveless cowl neckline, pleating
    • Spaghetti straps
    • Cutout at the midriff
    • Midi-length silhouette, high side slit
    • Satin fabric
    • Form-hugging fit, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-1316

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: BLACK, RED, NAVY

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

    Product Badge:
    • Sale
  • Kathleen Velvet One-Shoulder Midi Formal Dress

    Special Occasion

    Sleek and sculpted, the Kathleen velvet midi dress captivates with its one-shoulder neckline, bodycon fit, and a daring slit perfect for nights that demand a striking silhouette.

    Fit & Features

    • Velvet fabric, stretchy knit lining
    • One-shoulder neckline
    • Adjustable shoulder strap
    • Front slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, engagement parties, rehearsal dinners, birthdays, cocktail parties, semi-formal soirees, date nights

    Style Number/Barcode: 05001-000451

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: NAVY

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

  • Chic Style Ribbed Knit Off-Shoulder Midi Dress

    Minimal effort, major effect. This off-shoulder ribbed knit midi dress is your go-to for sleek confidence with a side of chic style. Pairs perfectly with a red lip and your best “don’t need to try” attitude.

    Fit & Features

    • Ribbed knit fabric, plenty of stretch
    • Asymmetric off-shoulder neckline, fold-over design
    • Long fitted sleeves
    • High-cut side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5919

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

  • Femme Fatale Floral Velvet Midi Dress

    A little sheer, a lot stunning. This velvet floral bodycon midi dress hugs every curve in the best way possible, featuring a delicate floral overlay and barely-there straps for that effortlessly sultry vibe. Pair it with strappy heels for any dressy occasion.

    Fit & Features

    • Flocked velvet floral pattern, mesh-lined fabric
    • V-neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000576

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

  • Effortless Aura Long Sleeve Midi Dress

    Minimal effort, maximum effect. This off-the-shoulder ribbed midi dress hugs in all the right places with a soft stretch knit that’s made for cozy-chic moments. Style it with gold hoops and strappy heels for that quiet luxury vibe.

    Fit & Features

    • Soft rib knit fabric, sewn-in knit lining, moderate stretch
    • Foldover off-the-shoulder neckline
    • Fitted long sleeves
    • Center back slit
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000331

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

  • Kaylee Velvet Strapless Midi Formal Dress

    Special Occasion

    Sleek, sculpted, and ready to turn heads—The Kaley formal dress brings effortless allure to every RSVP. Cut from plush velvet, this strapless bodycon midi hugs your curves with a ruched front seam and flirty slit that was made for a slow-motion entrance.

    Fit & Features

    • Luxe velvet knit fabric lined with stretchy knit
    • Strapless neckline, padded bra cups
    • Back zipper and hook-eye closure
    • Front ruched seam and slit
    • Bodycon fit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, cocktail parties, formal celebrations, fancy date nights, birthdays, engagement parties, rehearsal dinners, upscale social events, art gallery openings

    Style Number/Barcode: 05001-000466

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: HUNTER, NAVY, PURPLE

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

  • Gabrielle Glitter Velvet Midi Formal Dress

    Special Occasion

    Effortless glamour, redefined. The Gabrielle formal dress shimmers softly with every move, crafted in glitter velvet that hugs your shape to perfection. The sleek side slit adds just the right touch of allure, making this midi the ultimate mix of timeless and unforgettable.

    Fit & Features

    • Glitter velvet-lined fabric with stretch
    • Sweetheart neckline, padded bra cups
    • Adjustable spaghetti straps
    • Back zipper and hook-eye closure
    • Side slit
    • Bodycon fit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, engagement parties, romantic date nights, anniversary dinners, birthdays, formal occasions, upscale cocktail parties

    Style Number/Barcode: 05001-000476

    Category Name: Midi Dresses

    Price: $64.90

    Availability: In Stock

    Available Color: NAVY

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