Midi Dresses

Show filters
Sort:
Size
Color
Price
All filters
Sort
Loading...

Product Recommendations

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.

  • Lissi Formal Lace And Sequin Dress

    Bring the sparkle as you shine in our Lissie dress! She features a dazzling sequin embellished lace bodice, a round neckline, a plunging sweetheart neckline and fitted unlined long sleeves. Her slim fit bodice leads to a midi length silhouette accented with a side slit. Dress is composed of a combination crepe and lace fabric that offers a curve hugging fit with a moderate stretch. Includes a knit lining and back zipper closure.

    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: 05001-0234

    Category Name: Midi Dresses

    Price: $29.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Into The Florals Dress
    Immerse yourself in all the floral print you can take! This flower bomb features a cowl neck, adjustable narrow straps that create an X back, and a slim fit. Dress is composed of a casual knit fabric with a lightweight feel that offers plenty of stretch. Dress is unlined.

    Style Number/Barcode: 05102-3105

    Category Name: Midi Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Zest Lace-Up Midi Dress

    Fresh and sweet, this satin midi slip dress will make you shine. Dress features a cowl neck, crisscross spaghetti straps with lace-up ties, and a slim skirt with back zip. Dress is made from a smooth, satin-like material with a touch of stretch.

    Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0288

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Chic Midi Dress

    Turn heads in this off the moment chic midi! The dress features a sleeveless bodice, a deep V neckline, tank like shoulder straps that lead to a cross back followed by a cut out, a vertical seam running down the front and back, and a mid-length, form hugging fit with a small slit at the back hem. The dress is composed of a thick nylon ponte knit fabric that offers moderate stretch.

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

    Style Number/Barcode: 05101-0185

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sultry And Spotted Midi Dress

    Spotted! You in a sleek and sultry midi dress!

    Fits & Features

    • Adjustable Spaghetti Straps
    • Square Back I Structured Sweetheart Neckline With Padding
    • Midi Length Silhouette
    • Velvet-Like Fabric I Leopard Print Design
    • Curve Hugging Fit I Plenty Of Stretch

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

    Style Number/Barcode: 05103-0254

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Over Cut Out Midi Dress

    Take control of the room in a midi dress that says it all! Featuring a square neckline, spaghetti straps, and a curve hugging fit. Dress is one piece, with a cut out detail below the chest. Skirt of the dress features a high slit at one side and a hem that hits right above the knee.

    Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

     

    Style Number/Barcode: 05101-0184

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Muriel Illusion Lace Crepe Dress

    Special Occasion

    Strategic paneling and ever-sultry lace make our Muriel dress a sophisticated standout for evening. She features long lace sleeves, a back zip, a sweetheart bodice with lightly padded, contrast-paneled bust and lace-trimmed waist, and a body con, midi-length slim skirt. Muriel is made from a woven crepe material with a touch of stretch. 

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-0225

    Category Name: Midi Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ingrid Formal Satin Halter Dress

    Special Occasion

    Reveal your minimalistic charm in the Ingrid formal satin midi dress to make a remarkable impression! This dress embodies beauty and grace in a classic halter neckline and curve-hugging silhouette, while the low back flaunts your sultriness!

    Fit & Features

    • Premium satin fabric, no stretch
    • Sleeveless halter neckline
    • Tie-back neck closure
    • Low cowl back design
    • Curve-hugging silhouette, front slit, midi-length hem
    • Runs true to size

     

    Where to Wear:

    Weddings, rehearsal dinners, engagement parties, bridal showers, bachelorettes, date nights, black tie galas, birthdays, fancy dinner parties, anniversaries

    Style Number/Barcode: 05001-000421

    Category Name: Midi Dresses

    Price: $49.90

    Availability: In Stock

    Available Color: MOCHA, HUNTER

    Available Size: XS, S, M, L

  • Strappy Styles Midi Dress

    Strappy and stylish, this midi dress will freshen up your wardrobe. It features a sleeveless bodice, spaghetti straps, a wrap front V neckline, an open back with bar strap details, and a mid-length, form hugging fit. The dress is composed of a crepe fabric, offering moderate stretch, and includes a knit lining.

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

    Style Number/Barcode: 05103-0278

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Stunning Midi Dress

    Simply stunning is what you are in this trendy knit midi dress.

    Fits & Features

    • Bungee Spaghetti Straps
    • Square Neckline
    • Curve-Hugging Fit
    • Midi Length Silhouette
    • Soft Brushed Knit Composition | Fully Lined
    • Offers Plenty Of Stretch

     

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

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

    Style Number/Barcode: 05102-0175

    Category Name: Midi Dresses

    Price: $10.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Over You Sleeveless Midi Dress

    Show us who is boss in sleek midi! This mid length dress features a crew neckline, and a sleeveless bodice. Hem is tailored to a mid calf length, and dress is composed of a ponte material that offers moderate stretch. Throw on some heels and walk the walk!

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

    Style Number/Barcode: 05102-0189

    Category Name: Midi Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spark A Convo Midi Dress

    Be bold and daring in this off the moment midi dress. It features a sleeveless bodice, spaghetti straps that lead to a cross back, a wired notch V neckline with vertical seam detailing, a high waist seam, a ruched side detail, and a wrap front, asymmetrical hem. The dress is composed of a crepe fabric that offers moderate stretch.

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

    Style Number/Barcode: 05103-0299

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Forever Beauty Puff Sleeve Floral Chiffon Midi Dress

    This breezy floral chiffon midi dress will forever be a beautiful style for bridal showers, parties, and brunches! The airy sheer chiffon fabric is accented with a dainty floral print for a soft feminine vibe and includes a knit lining for coverage. The mid-length dress features a ruched square neckline detailed with a keyhole cutout and tie-front design, adorable short puff sleeves with elastic cinched hems, fitted high waist seams, and a chic high front slit for added movement on the flowy A-line silhouette. Complete the look with heels.

    Fit & Features

    • Floral print
    • Sheer chiffon fabric with stretchy knit lining
    • Ruched square neckline, keyhole cutout with tie-front
    • Short puff sleeves, back zipper with hook and eye closure
    • High front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3033

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Miss Flirtatious Maxi Dress

    Feeling flirty? We see you Miss flirtatious! This piece features a square neckline and thin straps that lead to a square back. The maxi dress has a cut out detailing under the chest area, cup lining, as well as a knot front at the hip. The high side slit shows off a little leg but not too much with the skirt style hem underneath! This gorgeous dress is composed of a ribbed soft knit material that offers moderate stretch.

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

    Style Number/Barcode: 05101-0210

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Stunner Faux Suede Dress

    Lead your squad with this stylish stunner of a dress! It features a sleeveless bodice, spaghetti straps, a V neckline, a square back with a hidden zipper closure, and a mid-length, form hugging fit. The dress is composed of a smooth faux suede fabric that offers moderate stretch.

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

    Style Number/Barcode: 05102-0199

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming And Chic Midi Dress

    This charming and chic midi dress will turn your look into a classic. It features a sleeveless bodice, a high round neckline, a back zipper closure, flattering vertical seam detailing along the bust, and a mid-length, curve hugging fit. The dress is composed of a ponte knit fabric that offers moderate stretch.

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

    Style Number/Barcode: 05102-0190

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunner In Lace Midi Dress

    Make a stunning entrance in this gorg lace midi dress! It features an off the shoulder popover neckline, a slim fit and a midi length. The dress is composed of a sheer lace fabric with a full knit lining and offers 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: 05101-0113

    Category Name: Midi Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Courtney Formal Glitter Wrap Midi Dress

    Special Occasion

    Get ready to strike a pose in the dazzling Courtney formal glitter dress at rehearsal dinners, weddings, or dressy birthdays! She features a sleeveless square neckline, tank shoulder straps, a form-hugging silhouette, and a side pleated seam that creates the chic wrap hem with a flirty slit. The formal dress is composed of a crepe glitter knit fabric with a moderate stretch. Complete the look with statement fringe earrings.

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • Form-hugging silhouette, side pleated seam
    • Slit, wrap midi-length hem
    • Crepe glitter knit fabric, moderate stretch
    • Bra-friendly design
    • Runs true to size

    Style Number/Barcode: 05001-1728

    Category Name: Midi Dresses

    Price: $54.90

    Availability: In Stock

    Available Color: BLACK, RED, WHITE-2

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

  • Dreamlover Colorblock Dress

    You're looking like someone's dreamlover tonight, bb! This sleeveless bodycon dress features a V neckline, spaghetti straps and an elasticized back for slip-on styling. It's designed with panels throughout for a contemporary look. Constructed of partially lined crepe fabric with 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: 05101-0221

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Such A Classic Midi Dress

    You love a classic look, and this chic and sophisticated midi dress is a definite must for your wardrobe!

    Fits & Features

    • Spaghetti Straps
    • V Neckline
    • Square Back
    • Mid-Length 
    • Form Hugging Fit With High-Low Trumpet Hem
    • Crepe Composition
    • Moderate Stretch

    Style Number/Barcode: 05101-0128

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Botanical Beauty Midi Dress
    This botanical print dress features a square ruffled neckline, elastic ruffle straps and a straight bodice. The backing of the dress has a hidden zipper and  stretch smock detailing.This piece has a dark toned floral print and is mid-length with a smooth inner lining and a side slit.It is composed of a sheer chiffon-like material that offers a relaxed fit with minimal stretch. On a stroll through the park or a gals brunch date, this dress is bound to have heads turning!

    Model is 5'9" with a 32" bust, a 24" waist, and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0210

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Miss Midi Striped Dress

    Hey there miss midi, we see you! and we are on the same page too, filling our closet with midi dresses this season. This piece features a  v-neckline, attached dark neutral marbled buttons, and adjustable spaghetti straps that lead to a square back. This toned midi dress has a skinny stripe pattern and is composed of a soft knit material that offers maximum stretch. 

    Style Number/Barcode: 05102-3992

    Category Name: Midi Dresses

    Price: $8.97 $21.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Meet Me In Midi Dress
    Elevate your going-out attire with a Little Midi! Dress features a curve-hugging cut, all-over ribbing, spaghetti straps, and a V neck with cutout rectangular detail at center bust. Dress slips on and is made from a soft woven material with moderate stretch.

    Model is 5'6.5" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0227

    Category Name: Midi Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Stylish Sweater Dress

    Keep your adorable 'fit sassy and stylish with this perfect sweater dress! It features an off the shoulder square neckline, short sleeves, and a curve hugging, mid-length fit. The dress is composed of a ribbed sweater knit fabric that offers plenty of stretch.

    Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 06005-0004

    Category Name: Midi Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance