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.

  • Sweetheart Energy Strapless Midi Dress

    Serving main character vibes all night long! This strapless midi hugs in all the right places with a sleek bodycon silhouette and a sultry back slit that brings the drama. 

    Fit & Features

    • Smooth knit fabric with a sheen, moderate stretch, stretchy lining
    • Strapless neckline with pleated bust detail
    • Sleek bodycon silhouette
    • Midi length with center back slit
    • Runs true to size

    Style Number/Barcode: 05101-000015

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: BURGUNDY

    Available Size: S, M, L, XL

  • Olivia Eyelash Lace Tulle Party Dress

    Special Occasion

    The Olivia party dress would be the perfect option for your upcoming bridal shower, rehearsal, or engagement party! She features a sleeveless bodice, spaghetti straps that lead to a sheer eyelash lace back with a lower cut out, and an eyelash lace front with a V neckline and a nude lining. Her high waist flows out to a sheer tulle tea-length skirt with a knit lining for an effortlessly pretty look. Pair this dress with rhinestone duster earrings and a dainty rhinestone bracelet.

    Fit & Features

    • Spaghetti straps
    • Sheer eyelash lace back
    • Lower back cut out
    • Eyelash lace front with a nude lining
    • V neckline
    • Side zipper and hook and eye closure
    • High waist leading to a sheer tulle tea-length skirt
    • Knit lining

    Style Number/Barcode: 05001-0393

    Category Name: Midi Dresses

    Price: $29.97 $72.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Majorly Chic Turtleneck Midi Dress

    Give your workwear look a majorly chic vibe when you wear this must-have midi dress! It features a sleeveless bodice, a trendy turtleneck, and a mid-length, curve-hugging silhouette. Layer on an oversized blazer and style with strappy heels for the perfect outfit for the office.

    Fit & Features

    • Sleeveless bodice
    • Turtleneck
    • Mid-length
    • Form-hugging fit, moderate stretch 
    • Viscose crepe fabric
    • Double-lined

    Style Number/Barcode: 05102-0911

    Category Name: Midi Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart Of Glam Ruched Midi Dress

    Bring the romantic vibes in this casually-chic midi dress! It features a sleeveless bodice with a square neckline, bungee spaghetti straps, a square back, ruched detailing, and a mid-length, curve-hugging silhouette. Pair this dress with strappy heels and a sleek clutch to complete your look.

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • Square back
    • Ruched detailing
    • Mid-length, form-hugging fit
    • Lined knit fabric with plenty of stretch

     

    SHOP ALL HEART OF GLAM COLLECTION

    Style Number/Barcode: 05102-1104

    Category Name: Midi Dresses

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beautiful Bloom Ruched Midi Dress

    Showcase your beauty in this stylish floral printed midi dress! It features spaghetti straps, a square neck and back, ruched detailing, and a mid-length, curve-hugging fit. Pair this dress with strappy heels and a rhinestone necklace for a romantic date night.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Ruched detailing
    • Mid-length
    • Form-hugging silhouette
    • Floral print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0949

    Category Name: Midi Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Such A Babe Ruched Midi Dress

    Yes babe, show off your gorgeous curves in this figure-flattering midi dress. It features thick and thin spaghetti straps, a cowl neckline, ruched detailing, and a mid-length, form-hugging fit. The knit fabric offers plenty of stretch for comfortable wear. Pair this dress with clear mules and a sleek clutch.

    Fit & Features

    • Thick and thin spaghetti straps
    • Cowl neckline
    • Square back
    • Ruched
    • Mid-length, form-fitting style
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05101-0930

    Category Name: Midi Dresses

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Mood Ribbed Knit Maxi Dress

    We're in the mood for basics! Slay in this dress that keeps it effortlessly chic. The dress features a trendy turtle neck, long sleeves, and a maxi length silhouette with a high center back slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with sneakers to nail those low-key vibes.

    Fit & Features

    • Turtle neck
    • Long sleeves
    • Maxi length silhouette
    • High center back slit
    • Ribbed knit fabric
    • Plenty of stretch
    • Form-hugging fit

    Style Number/Barcode: 05102-1117

    Category Name: Midi Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trend Alert Ribbed Knit Midi Dress

    Hey, trendsetter! Stun in a ribbed midi dress for your next date night with bae! The dress features a V-neckline, long sleeves, a bar strap accent at the back, and a midi length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules

    Fit & Features

    • V-neckline
    • Long sleeves
    • Bar strap accent at the back
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06005-0803

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Luxe Velvet Wrap Front Midi Dress

    Get a luxe look for your next holiday party in this gorgeous velvet midi dress. It features spaghetti straps, a wrap front creating a V neckline, and a mid-length, curve-hugging silhouette. Pair this dress with a rhinestone choker necklace and strappy heels.

    Fit & Features

    • Spaghetti straps
    • Wrap front
    • V neckline
    • Mid-length
    • Form-hugging fit
    • Velvet fabric
    • Moderate stretch

    Style Number/Barcode: 05101-0925

    Category Name: Midi Dresses

    Price: $17.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crush Season Floral Mesh Midi Dress

    Looking like a walking heart-eye emoji. This off-the-shoulder bodycon hugs every curve, with flirty ruching and a sweetheart neckline that brings serious date night energy. 

    Fit & Features

    • Floral print, mesh fabric, sewn-in knit lining
    • Off-the-shoulder sweetheart neckline
    • Padded bra cups, short-sleeve cuffs
    • Back zipper and hook-eye closure
    • Side ruched seams
    • Bodycon silhouette, midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-000075

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Knit Basic Midi Dress

    Bring it back to basics in a ribbed dress that showcases your curves in all the right places. The dress features a scoop neckline, long sleeves, and a midi length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties

    Fit & Features

    • Scoop neckline
    • Long sleeves
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06005-0800

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Cute and Casual Ribbed Midi Dress

    Keep it cute and casual in a knit dress that is perfect for a quick coffee run or a casual date with bae. The dress features a scoop neckline, long sleeves, a midi length silhouette, and composed of a ribbed brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers

    Fit & Features

    • Scoop neckline
    • Long sleeves
    • Midi length silhouette
    • Ribbed
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1042

    Category Name: Midi Dresses

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Style Ruched Midi Dress

    Showcase that sultry style in this stunning midi dress! It features a sleeveless bodice with a wrap front V neckline, spaghetti straps that lead to a cross back and a strappy back with a tie closure, and a mid-length, curve-hugging silhouette with ruched detailing. Pair this dress with sleek heels and a glam rhinestone ring pack.

    Fit & Features

    • Wrap front V neckline
    • Spaghetti straps that lead to a cross back
    • Strappy back with a tie closure
    • Mid-length, form-hugging fit
    • Ruched detailing
    • Knit fabric with moderate stretch

    Style Number/Barcode: 05101-0928

    Category Name: Midi Dresses

    Price: $21.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Addison Stretch Satin Long Sleeve Midi Dress

    Special Occasion

    Make a dramatic entrance in our stunning Addison midi dress! She features long fitted sleeves, a wired notch front V neckline, a high waist, and a mid-length, curve-hugging silhouette with a sultry back slit. Pair this dress with a rhinestone choker necklace for a glam factor.

    Fit & Features

    • Long fitted sleeves
    • Wired notch front V neckline
    • Back zipper and hook and eye closure
    • Princess seams and high waist
    • Mid-length, form-hugging fit
    • Back slit
    • Stretch satin-like fabric

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0498

    Category Name: Midi Dresses

    Price: $19.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Sweetheart Ribbed Knit Midi Dress

    Showcase the stylish sweetheart you are in this trendy ribbed knit midi dress! It features a sweetheart neckline with bust seam detailing, a mid-calf length and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch for comfortable wear. Pair this dress with heeled booties and layer on a faux leather jacket for an edgy vibe.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline
    • Bust seam detailing
    • Mid-length, form-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-1040

    Category Name: Midi Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Shine On Sequin Midi Dress

    Shine on in a sequin midi dress that brings the glamour. The dress features a sleeveless V-neckline, adjustable spaghetti straps, and a geometric sequin pattern. The dress is composed of a lined mesh fabric that offers a form-hugging fit with minimal stretch. Complete look with a dainty rhinestone bracelet.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Back zipper and hook and eye closure
    • Geometric sequin pattern
    • Midi length silhouette
    • Lined mesh fabric
    • Form-hugging fit

    Style Number/Barcode: 05101-0899

    Category Name: Midi Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kate Formal Crepe Midi Dress

    Special Occasion

    Keep your look simply elegant and polished in our essential Kate dress! She features an off-the-shoulder neckline, a fold-over accent, and princess seams leading to her figure-flattering midi-length silhouette with a sultry side slit. The dress is composed of a crepe fabric that offers a moderate stretch. Complete your look with a sleek clutch and rhinestone earrings.

    Fit & Features

    • Off-the-shoulder foldover neck
    • Strapless bra recommended
    • Vertical princess seams
    • Midi-length silhouette with high side slit
    • Crepe knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-4043

    Category Name: Midi Dresses

    Price: $14.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The Every Day Ribbed Knit Midi Dress

    This knit dress is perfect for your everyday occasions! Layer with chunky sneakers and dainty rings to create a chic back to school outfit this season. The dress features a mock neck, long sleeves, a midi-length silhouette, and composed of a soft to the touch ribbed knit fabric that enhances curves.

    Fit & Features

    • Mock neck 
    • Long sleeves
    • Midi length silhouette
    • Lined ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0960

    Category Name: Midi Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Allure Strapless High Slit Midi Dress

    Show off casual allure in this curve-flaunting midi dress featuring a strapless sweetheart neckline, keyhole cutout below the bust, and high-cut side slit.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Strapless sweetheart neckline, metal U-ring insert
    • Keyhole cutout below the bust
    • High side slit
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-000110

    Category Name: Midi Dresses

    Price: $42.90

    Availability: In Stock

    Available Color: OLIVE

    Available Size: XS, S, M, L

  • Alina Formal iridescent Sequin Midi Dress

    Special Occasion

    Sparkle and shine in a dress that brings the glamour to your evening. Alina features a sleeveless V-neckline with a sheer mesh inset, tank-like straps, an iridescent sequin scroll print, and a midi length silhouette. Aline is composed of a lined mesh fabric that offers a form hugging fit with a slight stretch. Complete your formal outfit with glitter heels and a dainty rhinestone bracelet

    Fit & Features

    • Sleeveless V-neckline with mesh inset
    • Tank-straps
    • Iridescent Sequin scroll print
    • Midi length silhouette
    • Lined mesh fabric
    • Form hugging fit, minimal stretch
    • Back zipper closure 

     

    Special Occasion products cannot be returned to any retail locations.  

    Style Number/Barcode: 05001-0432

    Category Name: Midi Dresses

    Price: $36.97 $79.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Kelly High Slit Satin Midi Dress

    Special Occasion

    Elevate your special evening outfit in our chic Kelly dress. She features a sweetheart neckline, long sleeves, vertical seams at the bust, and a midi length silhouette with a high side slit. The dress is composed of lined stretch satin fabric that offers a form hugging fit with a moderate stretch. Complete your look with a dainty rhinestone bracelet.

    Fit & Features

    • Sweetheart neckline
    • Long sleeves
    • Vertical seams at the bust
    • Midi length silhouette
    • High slit
    • Lined stretch satin fabric
    • Form hugging fit, moderate stretch


    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0506

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Nora Satin Open Back Midi Dress

    Special Occasion 

    Strike a stunning look in a dress that brings the elegance! Nora features a daring open back, a ruched center back seam, a high round neckline, and a midi length silhouette with a high side slit. Nora is composed of a lined stretch satin fabric that offers a form hugging fit. Complete your look with rhinestone hairpins

    Fit & Features

    • High round neckline
    • Long sleeves
    • Open back with sleek bar strap accent 
    • Ruched center back seam with lower back zipper
    • Midi length silhouette with high side slit
    • Lined stretch satin fabric 
    • Form hugging fit


    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0505

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Brushed Knit Sleeveless Crew Neck Midi Dress

    Slip into this adorable sleeveless midi dress for a chic everyday look! It features a crew neckline and a mid-calf length, curve-hugging silhouette. The brushed knit fabric has a soft cashmere-like feel. Pair this dress with chunky sneakers for a casual vibe or heeled booties for a date night.

    Fit & Features

    • Crew neckline
    • Tank-like shoulder straps
    • Mid-length, form-hugging fit
    • Brushed knit fabric

    Style Number/Barcode: 05102-0984

    Category Name: Midi Dresses

    Price: $15.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Velvet Luxe Bodycon Midi Dress

    Bring the luxe in a velvet dress that brings sophistication to your cocktail affair. The dress features an off the shoulder neckline with short sleeves, a midi length silhouette, and a bodycon fit. Complete your evening outfit with a pair of clear heels and a dainty rhinestone bracelet

    Fit & Features

    • Off the shoulder neckline
    • Short sleeves
    • Midi length silhouette
    • Bodycon fit
    • Lined velvet fabric
    • Slight stretch 

    Style Number/Barcode: 05101-0901

    Category Name: Midi Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance