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.

  • Ginger Show Stopper Heat Stone Dress
    Special Occasion 

    Make a stunning impression as you shine under the spotlight in our Ginger black dress! She features an all over black hue, a scoop neckline, adjustable narrow straps and a flattering midi length silhouette. Her all over partially lined mesh fabric features gleaming heat stones! Ginger includes a built in bodysuit lining that features a cheeky bottom with a snap button closure. Dress offers a form hugging fit that offers a moderate stretch. Be sure to pick up the matching duster to complete your show stopping look! 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-3997

    Category Name: Midi Dresses

    Price: $20.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Better In Basics Ribbed Knit Sweater Dress

    Sometimes, basic is better, like this adorable ribbed knit sweater dress! It features a flattering V neckline, a mid-length, curve-hugging silhouette, and a front slit. Pair this sweater dress with chunky sneakers for a casual-chic vibe.

    Fit & Features

    • Thin adjustable shoulder straps with gold metal detailing
    • V neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Front slit
    • Ribbed sweater knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06005-0862

    Category Name: Midi Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Comfy-Chic Ribbed Knit Midi Dress

    Look so comfy-chic in this adorable ribbed knit midi dress! It features a deep V neckline, adjustable spaghetti straps, and a mid-calf length curve-hugging fit. Pair this dress under a sleek faux leather moto jacket and accessorize with a layered necklace for a date night out.

    Fit & Features

    • V neckline
    • Adjustable spaghetti straps
    • Mid-length, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1041

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Refined Charm Flocked Velvet Halter Midi Dress

    The midi dress features a sleeveless halter neckline with a single halter neck strap, a floral flocked velvet pattern, and a high side slit. Complete the cocktail outfit with sleek stiletto heels.

    Fit & Features

    • Lined mesh fabrication
    • Sleeveless halter neckline
    • Floral flocked velvet pattern
    • High side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3809

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK, WINE

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

  • Ruched Stunner One Shoulder Midi Dress

    Stun in a one-shoulder dress that brings the charm to your next night out. The dress features a one-shoulder neckline, a tank strap, a ruched side seam, and a midi length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.

    Fit & Features

    • One-shoulder neckline
    • Tank strap 
    • Ruched side seam
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05101-0912

    Category Name: Midi Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Knit Crew Neck Midi Dress

    Fall for a knit dress to usher in those cozy vibes this season! The dress features a crew neckline, short sleeves, and is composed of a textured knit fabric with a moderate stretch. The dress offers a form-hugging fit. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Midi-length silhouette 
    • Textured knit fabric with knit lining
    • Moderate stretch
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-0941

    Category Name: Midi Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • That Classic And Chic Vibe Ruched Midi Dress

    This sexy ruched midi dress will give you that classic and chic vibe! It features a flattering one-shoulder neckline and a mid-length, form-hugging fit with ruched detailing to enhance your curves. The double-lined knit fabric offers plenty of stretch. Pair this midi dress with duster earrings to level up the look.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Mid-length, form-hugging fit
    • Ruched detailing
    • Double-lined knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05101-0919

    Category Name: Midi Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keepin' Knit Simple Ribbed Midi Dress

    Keep it simple and stylish in this basic ribbed knit midi dress! It features long fitted sleeves and a mid-length, form-hugging silhouette to enhance your curves. Pair this dress with heeled booties for a casual date night look perf for the cooler months.

    Fit & Features

    • Long fitted sleeves
    • V neckline
    • Mid-length, form-fitting style
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-0890

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Curves Ahead Sleeveless Ruched Midi Dress

    Showcase curves in a ruched midi dress that elevates your night-out look! The dress features a sleeveless mock neckline, a ruched body, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit and a moderate stretch. Complete the look with clear mules.

    Fit & Features

    • Sleeveless mock neckline
    • Ruched body
    • Midi-length silhouette
    • Smooth knit fabric, knit lining
    • Form-hugging fit
    • Moderate stretch
    • Style runs small

    Style Number/Barcode: 05101-0956

    Category Name: Midi Dresses

    Price: $6.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Buttoned Up Off The Shoulder Midi Dress

    Get all buttoned up in this adorable off the shoulder midi dress! It features a complete button-down front with a curve-hugging, mid-length fit. Perfect for everyday, pair this dress with heeled booties to take your look into fall.

    Fit & Features

    • Off the shoulder neckline
    • Short fitted sleeves
    • Complete button-down front
    • Mid-length, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0943

    Category Name: Midi Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Open Back Ruched Ribbed Knit Midi Dress

    Style up this basic ribbed knit midi dress for the perfect everyday look! It features a partial lower open back, ruched detailing and a curve-hugging mid-length silhouette. Pair the dress with chunky sneakers to get that casual, cute vibe.

    Fit & Features

    • Scoop neckline
    • Long fitted sleeves
    • Partial lower open back
    • Ruched detailing
    • Form-hugging fit
    • Midi length
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0977

    Category Name: Midi Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • In Knit To Win It Midi Dress

    You'll be totally in it to win it in this adorable knit midi dress! It features a double-lined knit fabric and a mid-length, curve-hugging silhouette. Wear this dress with chunky sneakers for an adorable everyday look.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Mid-length form-hugging fit
    • Double lined knit fabric

    Style Number/Barcode: 05102-0877

    Category Name: Midi Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Alex Satin V-Neck Slit Midi Formal Dress

    Special Occasion

    Designed to command the room, the Alex formal dress is all sleek confidence with its satin fabric, sculpting midi silhouette, and dramatic plunge neckline. A subtle side slit adds just the right touch of allure, perfect for the kind of entrance that turns heads.

    Fit & Features

    • Stretch satin fabric
    • Plunge V-neckline, wide shoulder straps
    • Back zipper and hook-eye closure
    • Side slit
    • Form-hugging silhouette\
    • Midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, date night, birthdays, black tie galas, bridal showers, anniversaries, dinner parties, receptions, cocktail soirees

    Style Number/Barcode: 05001-000233

    Category Name: Midi Dresses

    Price: $59.90

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M

  • Sultry Chic Ruched Midi Dress

    Get a sultry chic vibe in this stunning ruched midi dress! Featuring a trendy square neckline and ruched detailing to enhance your natural curves making this dress a must-have for date night! Pair it with some sleek heels to level up the look.

    Fit & Features

    • Sleeveless, square neck
    • Spaghetti straps
    • Ruched detailing
    • Bodycon silhouette
    • Midi-length hem
    • Smooth knit fabric, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05101-0771

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sydney High Neck Scalloped Lace Midi Dress

    Special Occasion

    Make a stunning entrance in our gorgeous Sydney midi dress! She features a flattering high neck with an open back and a curve-hugging mid-length silhouette. The dress has pretty scalloped lace detailing and a chic back slit. Pair this pretty dress with some clear heels for your next date night with bae.

    Fit & Features

    • High neck
    • Open back
    • High waist seam
    • Mid-length form-hugging fit
    • Back slit
    • Scalloped lace fabric
    • Short lining that hits mid-thigh

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0357

    Category Name: Midi Dresses

    Price: $29.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mila Formal High Slit Midi Dress

    Special Occasion

    Keep it simply stunning in our Mila formal dress! Her elegant design captivates from the moment you enter the room of your special occasion. Mila features a sleeveless V-neckline, vertical seams at the bust, and a curve-hugging midi silhouette with a high side slit. She is composed of a stretch knit fabric with a subtle sheen finish. Complete your look with clear heels

    Fit & Features

    • Sleeveless V-neckline
    • Princess seams at the bust
    • Adjustable spaghetti straps
    • Midi length silhouette
    • High side slit
    • Strtech knit fabric, fully lined
    • Form hugging fit, moderate stretch 

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0467

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Valeria Formal Off-The-Shoulder Crepe Midi Dress

    Special Occasion 

    Bring the sophistication in our Valeria dress to your elegant affair. Valeria features a charming off-the-shoulder neckline with short sleeves, sleek spaghetti straps, a pleated sweetheart bust, and a curve-hugging midi-length silhouette with a back center slit for an alluring detail. She is composed of a form-fitting crepe fabric that offers retention and a moderate stretch. Complete your formal outfit with clear heels.

    Fit & Features

    • Off-the-shoulder, short sleeves, spaghetti straps
    • Sweetheart pleated bust, adhesive bra recommended
    • Back center slit, zipper closure
    • Form-fitting silhouette
    • Midi-length hem
    • Crepe fabric, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05001-0472

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lovin' Knit Basic Midi Dress

    We love a knit dress to keep on trend this season! Throw on this must-have dress for a casual day out. The dress features a trendy square neckline, fitted long sleeves, and a midi length silhouette. Complete look with chunky sneakers for a casual vibe. 

    Fit & Features

    • Square neckline
    • Long sleeves
    • Midi length silhouette 
    • Knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0853

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Buttoned In Sassy Stripes Midi Dress

    Button up in a striped dress that keeps your look so casually cute! The dress features a fab button-down front, tie spaghetti straps, and a striped pattern. Complete your look with clear mules for a stylish look. 

    Fit & Features

    • Sleeveless scoop neckline
    • Tie spaghetti straps
    • Button-down front
    • Striped pattern
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0569

    Category Name: Midi Dresses

    Price: $9.97 $23.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • She's A Showstopper Ruched Midi Dress

    Make them stop and stare at this stunning dress that commands attention! The sleek midi dress features a trendy square neckline, sleek bungee straps, and a curve-hugging ruched midi silhouette. Complete your look with duster earrings for your night-out outfit.

    Fit & Features

    • Sleeveless square neckline, bungee straps
    • Strapless bra recommended
    • Side ruched detailing
    • Midi-length bodycon silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0848

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Char Formal Sequin Asymmetrical Midi Dress

    Special Occasion

    Stun in a sequin dress that brings the shimmer to enlighten your evening! Our Char dress features a plunging V-neckline, sleek spaghetti straps and an asymmetrical midi length hem. Her sequins shine from all your best angles and pair well with chrome heels and a satin clutch for your special evening.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Sequins
    • Asymmetrical midi length hem
    • High side slit
    • Form hugging fit


    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05002-1119

    Category Name: Midi Dresses

    Price: $29.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crush Hour Floral Bodycon Midi Dress

    Made for compliments and second glances. This mesh midi hugs in all the right places with a V-notch neckline that’s total main character energy.

    Fit & Features

    • Sheer mesh-lined fabric, floral print
    • V-notch neckline with ruched bust
    • Tank straps
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3535

    Category Name: Midi Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Into You Basic Knit Midi Dress

    We're so into this dress that can be dressed up for a date night or keep it casual with layers. The dress features a sleeveless square neckline, tank-straps that offer support, and a curve-hugging midi-length silhouette. Complete look with ankle booties or mules

    Fit & Features

    • Sleeveless square neckline
    • Tank straps
    • Midi length silhouette
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0912

    Category Name: Midi Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Slay Every Day Basic Scoop Neck Midi Dress

    Slay every day in a basic midi dress that is effortlessly chic. The dress features a sleeveless scoop neckline, tank-straps, and a midi length silhouette. The double lined smooth knit fabirc offers a comfortable feel. Complete your look with chunky sneakers and stud earrings to nail low-key vibes.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-straps
    • Midi length silhouette
    • Double lined smooth knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0908

    Category Name: Midi Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free