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.

  • Chic Intentions Off-The-Shoulder Midi Dress

    Effortlessly chic and subtly bold, this off-the-shoulder mesh midi dress pairs sleek ruching with a curve-hugging fit—made for cocktail parties, rooftop soirées, and everywhere you own the room.

    Fit & Features

    • Mesh fabric with knit lining, high stretch
    • Off-the-shoulder design, short-sleeved cuffs
    • Cowl neckline
    • Ruching
    • Midi-length hem
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000382

    Category Name: Midi Dresses

    Price: $38.90

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Need For Basics Ribbed Midi Dress

    Get your need for basics in a dress that can be dressed up or dressed down for your next day out. The dress features a trendy square neckline, tank-like straps, and a midi length silhouette. Complete your look with clear heels and statement hoop earrings. 

    Fit & Features

    • Sleeveless square neckline
    • Tank-like straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit 

    Style Number/Barcode: 05102-0871

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Vibes Knit Midi Dress

    Rock those basic vibes in a dress that keeps it comfortable and chic. The everyday dress features a sleeveless bodice, a v-neckline with notched detail, and a midi length silhouette. Complete your look with chunky sneakers and a chunky necklace to create a trendy streetwear look. 

    Fit & Features

    • Sleeveless bodice
    • V-neckline with notched detail 
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit 
    • Moderate stretch 

     

     

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0924

    Category Name: Midi Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Rosey Slip Midi Dress

    Keep it rosey in this cute slip dress that keeps your look effortlessly pretty! Step out this season in a slip dress that features a pretty floral print, a high side slit and a midi length silhouette. Complete your look with clear heels and fringe earrings

    Fit & Features

    • Plunging v-neckline
    • Adjustable spaghetti straps
    • Floral print
    • High side slit
    • Midi length silhouette
    • Lightweight woven fabric
    • Relaxed fit

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0836

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Twist Back Ribbed Knit Midi Sweater Dress

    Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Open back with twist back detail
    • Mid-length silhouette
    • Form-hugging fit
    • Ribbed sweater knit fabric

    Style Number/Barcode: 06005-0846

    Category Name: Midi Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Chic Midi Sweater Dress

    Keep it chic and stylish in this knit midi sweater dress, a perf transitional piece into the new season! It features a curve-hugging fit and a mid-length silhouette. Pair the dress with some trendy heeled booties for that must-have fall look.

    Fit & Features

    • V neckline
    • Tank-like shoulder straps
    • Mid-length silhouette
    • Form-hugging fit
    • Ribbed sweater knit fabric

    Style Number/Barcode: 06005-0832

    Category Name: Midi Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Show Up Satin One-Shoulder Midi Dress

    Show them up, girl! Look elegantly sleek in this one-shoulder midi and walk right in looking like a million bucks! It features a curve-hugging silhouette with a thigh-high front slit. Complete the look with chrome heels.

    Fit & Features

    • One-shoulder neckline, single spaghetti strap
    • Asymmetric neckline
    • Ruching at the side slit
    • Midi-length silhouette
    • Satin-like fabric, pretty sheen finish 
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-0894

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirt Alert Floral Slit Midi Dress

    Leg pop approved. With a pleated waist and wrap-front slit, this floral midi dress brings the flirty vibes for any night out or dressed-up moment.

    Fit & Features

    • Stretch knit fabric with floral print
    • Square neckline, spaghetti straps
    • Side pleated seam
    • Front wrap slit
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000199

    Category Name: Midi Dresses

    Price: $44.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: XS, S, M, L

    Product Badge:
    • Back In Stock
  • Lovin' The Basics Cotton Midi Dress

    You'll be lovin' everything about this basic cotton midi dress! Featuring a crew neckline and a mid-length, curve-hugging fit, this dress will flatter your figure. Pair with some gold hoops and chunky sneakers for a laid back, casual vibe you can wear to hang out with your squad.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mid-length silhouette
    • Cotton fabric

    Style Number/Barcode: 05102-0926

    Category Name: Midi Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flowy Floral Woven Midi Dress

    Create an effortlessly pretty look in this floral woven midi dress! It features a trendy tie front detail and a flattering flowy mid-length silhouette. Pair the dress with block heels and gold hoops for the perfect date night outfit.

    Fit & Features

    • V neckline
    • Tie front detail
    • Three-quarter length flowy sleeves
    • Front waist cut out
    • Mid-length flowy fit
    • Floral printed woven fabric

     

    Model is 5'7" with a 32.5" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0962

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Trendy Tie Dye Midi Dress

    This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.

    Fit & Features

    • High rounded neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Tie dye print
    • Knit fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0866

    Category Name: Midi Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Flair Woven Midi Dress

    You'll have that total floral flair in this stunning woven midi dress! Featuring a V neckline and a flowy mid-length silhouette, this dress would be perfect for a fall date night. Pair with some clear heels and accessorize with gold hoops to let the dress make the statement.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline
    • Back zipper closure
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric


    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0915

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fall For Floral Woven Midi Dress

    Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0882

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Sleek Tie Shoulder Slip Dress

    Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.

    Fit & Features

    • Tie shoulder straps
    • Slight V neckline
    • Square back
    • Flowy mid-length fit
    • Woven fabric

     

    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0895

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strapless Tube Tie Dye Midi Dress

    Make a splash in a tie-dye dress that brings some serious summer vibes! Step out for that backyard bbq with the squad in this colorful midi dress. The dress features a strapless tube neckline, a tie-dye print, and a curve-hugging midi-length silhouette. Complete your summer outfit with clear heels

    Fit & Features

    • Sleeveless tube neckline
    • Tie-dye pattern
    • Midi length silhouette
    • Form hugging knit fabric
    • Moderate stretch 

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0831

    Category Name: Midi Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Paige Formal Off-The-Shoulder Scalloped Lace Dress

    Special Occasion 

    Enchant in our captivating Paige dress that brings elegance and grace to your special events! Perfect for the bride-to-be's Bridal Shower, Paige's scalloped lace fabric brings the charm. Paige features an off-the-shoulder neckline with scalloped lace trim, sheer short sleeves, a ribbon tie-waist belt, and a midi-length silhouette. Complete look with radiating rhinestone earrings.

    Fit & Features

    • Off-the-shoulder neckline with lace trim
    • Sheer short sleeves
    • Strapless or adhesive bra recommended
    • Tie-waist ribbon belt
    • Midi-length silhouette
    • Floral lace pattern
    • Relaxed fit
    • Runs true to size

     

    Style Number/Barcode: 05001-0441

    Category Name: Midi Dresses

    Price: $14.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Georgie Sweetheart A-Line Satin Midi Dress

    Special Occasion

    Let the Georgie satin midi dress charm you with the delicate lace trim, sweetheart neckline, and forever flattering A-line silhouette. Plus, the hidden side pockets keep your hands warm and are perfect for stashing your phone or lip gloss in!

    Fit & Features

    • Premium satin fabric, multiple woven tulle trim and satin linings
    • Lace trim sweetheart neckline, adjustable spaghetti straps
    • Built-in padded underwire bust
    • Back zipper and hook-eye closure
    • Hidden side pockets
    • A-line silhouette, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, garden parties, cocktail soirees, dressy celebrations, glam afternoon tea

    Style Number/Barcode: 05001-2719

    Category Name: Midi Dresses

    Price: $109.90

    Availability: In Stock

    Available Color: LIGHT, BLUE

    Available Size: XS, S

    Product Badge:
    • Ships Free
  • The Every Day Tube Midi Dress

    Step out in this staple dress to wear any day for any occasion! This midi dress is perfect for dressing up with heels to create a night out outfit or dressing down with sneakers for a casual coffee date. The dress features a sleek tube neckline and a midi length silhouette with a mini side slit. 

    Fit & Features

    • Sleeveless straight tube neckline
    • Midi length silhouette
    • Mini side slit
    • Knit fabric
    • Form hugging fit
    • Moderate stretch 

     

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

    Style Number/Barcode: 05102-0827

    Category Name: Midi Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Lillyanne Formal Satin Asymmetrical Midi Dress

    Special Occasion 

    Enchant them all with the captivating Lillyanne formal midi dress! She features a sleeveless bodice, a trendy cowl neckline, adjustable spaghetti straps for a customized fit, and a strappy cross-back design. Her high waist seam elongates your silhouette and leads to a mid-length skirt with an asymmetrical wrap hem creating a front slit. The midi dress is composed of a satin fabric that offers a curve-hugging fit with a moderate stretch. Complete the look with clear heels and a sleek satin clutch.

    Fit & Features

    • Sleeveless cowl neckline, adjustable spaghetti straps
    • Strappy cross-back design
    • Asymmetrical wrap skirt, back zipper closure
    • High waist seam, midi-length hem
    • Lined satin fabric, moderate stretch
    • Strapless or sticky bra recommended
    • Runs true to size

    Style Number/Barcode: 05001-0807

    Category Name: Midi Dresses

    Price: $29.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring the Flair Crepe Ruffled Dress

    Bring the flair in this ruffled dress for your next night out! The dress features a plunging V-neckline and a ruffled asymmetrical hem. The dress is composed of a form-hugging crepe fabric that embraces curves while providing a retention stretch. Complete your look with sleek heels and rhinestone earrings

    Fit & Features

    • Plunging V-neckline
    • Sleek spaghetti straps
    • Ruffled asymmetrical hem
    • Crepe fabric
    • Form hugging fit, moderate stretch 

     

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

    Style Number/Barcode: 05101-0823

    Category Name: Midi Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back High Slit Floral Dress

    Show off your affinity for florals in a dress that creates major head-turning appeal! Step out for brunch with your squad in this pretty in pink dress! The dress features a high round neckline, cap sleeves, a lower back keyhole, and a high side slit. Complete look with clear heels and mini purse.

    Fit & Features

    • High round neckline
    • Cap sleeves
    • Lower back keyhole
    • Floral print 
    • High side slit
    • Midi-length silhouette
    • Lightweight woven fabric

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0834

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Belted Sophistication Sleeveless Mini Dress

    Keep it chic in a belted dress that elevates you to a sophisticated and polished look. The dress features a sleeveless square neckline, spaghetti straps, side slit, and a belted waist with a rectangular buckle. Complete look with clear heels

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Belted waist with rectangular buckle
    • Mini length silhouette
    • Side slit
    • Ribbed knit fabric

     

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

    Style Number/Barcode: 06005-0684

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daria Formal Ruched Midi Dress

    Special Occasion 

    From the moment you enter the room, command attention with our head-turning Daria midi dress! Her ruched accents showcase curves to create a flattering hourglass illusion! Pair with sleek heels and clutch for a complete look! 

    Fit & Features

    • High Round Neckline
    • Plunging V-Shaped Back with Bar Strap Ties
    • Ruched Side Seams
    • Lined Smooth Knit Fabric
    • Form Hugging Fit
    • Moderate Stretch 

     

    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: 05001-0404

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stripe It Down Ribbed Button Down Midi Dress

    Keep it stunning in a striped dress that wows. Step out for brunch in this midi dress that features an off the shoulder neckline with a sweetheart bust, short sleeves, a button-down front, and narrow horizontal stripes. Complete your look with strappy mules and sleek hoops

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust
    • Short sleeves
    • Button-down front
    • Narrow horizontal stripes
    • Midi length silhouette with center front slit
    • Ribbed knit fabric, form-hugging fit


    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0795

    Category Name: Midi Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance