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.

  • Get The Ponte Cut Out Dress

    Make your point clear in this statement dress! It features a sleeveless bodice, a plunging wired V neckline, vertical princess seams, spaghetti straps and a sexy waist cut-out. The midi length silhouette hugs curves to create an hourglass illusion. Dress is composed of a ponte knit fabric that offers a moderate stretch.

    Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0429

    Category Name: Midi Dresses

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sneaky As A Snake Sequin Midi Dress

    Sneak into some snake print this season! This midi features a square neckline, spaghetti straps that lead to a square back, and a form fitting silhouette. Dress is designed with sequins and composed of a knit material that offers slight stretch and sow a subtle snake print pattern.

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

    Style Number/Barcode: 05103-0328

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Picturesque Cutie Corset Lace-Up A-Line Midi Dress

    Create a cute picturesque 'fit in this corset A-line midi dress! The corset bodice and lace-up back add a touch of allure to the sweet silhouette.

    Fit & Features

    • Woven fabric lined with stretchy knit
    • Sweetheart neckline, tie-front detail
    • Thin adjustable straps
    • Corset bodice, lace-up back
    • High waist seam
    • Midi-length A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3069

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Raegan Formal Sequin Midi Dress

    Special Occasion

    Bring the glitz and shine in our dazzling Raegan dress! She features a plunging V neckline, vertical princess seams along the bust, a double row of spaghetti straps, padded cups and a partially open back. Her slim fit bodice leads to a curve hugging midi length silhouette. She is composed of a lined mesh fabric adorned with sparkling sequins throughout. Dress offers a curve hugging fit with a minimal 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: 05001-0216

    Category Name: Midi Dresses

    Price: $19.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Katelyn Ruched Midi Dress

    Chic and fab, the Katelyn ruched midi dress is a new go-to. She features a sleeveless bodice, a Y neck with halter straps, a knot detail, and a front keyhole cut out, and a square back with a zipper closure. Her high waist band leads to a curve hugging skirt with ruched side details and a mid-length hem. The dress is composed of a stretchy knit fabric with a pretty sheen.

    Model is 5'8" 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: 05001-0238

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Satin Dreams Midi Dress

    We are totally obsessed with satin right now and we are guessing you are too! This midi dress features a v-neckline, thin spaghetti straps that lead to a square back and a hemline that flows into a floor length. Dress is composed of a satin like material that offers a relaxed fit with no stretch.

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

    Style Number/Barcode: 05102-0325

    Category Name: Midi Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Florence Heat Stone Midi Dress

    Special Occasion

    Show some class in our Florence! She has a v neckline, tank straps, and a form fit. Her hem hits below the knee and has a small slit at the side. She is composed of a knit material with a mesh overlay that is adorned with reflective heat stones. She offers moderate stretch, and a full lining. Pair with your favoirte black heels to complete the look! 

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

     

    Special Occasion products cannot be returned to any retail locations.

    Style Number/Barcode: 05001-4121

    Category Name: Midi Dresses

    Price: $24.97 $69.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lustrous Velvet Dress

    This simple velvet dress is all you need to stay trendy all season long! 

    Fit & Features 

    • Elastic Off The Shoulder Neckline
    • Short Sleeves
    • Midi Length
    • Velvet 
    • Fully Lined
    • Moderate Stretch 
      Model is 5'6 with a 32" bust, 23" waist and 34" hips. She is wearing a size small.

     

    Style Number/Barcode: 05101-7558

    Category Name: Midi Dresses

    Price: $12.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bring Knit On Midi Dress

    Bring on the style with this trendy basic knit midi! The dress features a mock neckline, long fitted sleeves, and a mid-length, curve hugging fit. Garment is composed of a brushed knit fabric with a knit lining, offering plenty of stretch.

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

    Style Number/Barcode: 05102-0178

    Category Name: Midi Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Add Some Flair Skater Dress

    Add some flair to your style with this adorable lace skater dress! It features an off the shoulder neckline with a sheer lace overlay, a high waist seam, and a flowy skater skirt with a high low hem. The dress is composed of a sheer lace fabric with a full knit lining and has moderate stretch.

    *Also available in Plus.

    Style Number/Barcode: 05101-0039

    Category Name: Midi Dresses

    Price: $18.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Basic Midi Dress

    Sometimes keeping it basic is the best way to go! This knit midi dress features a sleeveless bodice, tank-like shoulder straps, a scoop neck and back, a side slit, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.

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

    Style Number/Barcode: 05102-0268

    Category Name: Midi Dresses

    Price: $9.97 $20.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dinner Date Off-The-Shoulder Long Sleeve Midi Dress

    The perfect dinner date starts with this off-the-shoulder midi dress and ends with cocktails on the patio! The double-lined smooth knit fabric ensures a comfortable and smooth feel, while the midi-length hem adds a touch of elegance.  With its fitted long sleeves and ruched side seams, it offers a flattering bodycon fit that accentuates your curves. Complete the look in mules.

    Fit & Features

    • Double-lined, stretchy smooth knit fabric
    • Off-the-shoulder neckline
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3551

    Category Name: Midi Dresses

    Price: $48.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: XXS

  • Ruffle It Up Smocked Midi Dress

    Play up your look with this adorable ruffled and smocked midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back with a ruffle hem, ruffle tiers, and a stretchy smocked body with a mid-length form hugging fit. Dress is composed of a lightweight woven fabric.

    Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0341

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Vibes Knit Midi Dress

    Get those casual cute vibes in this adorable knit midi! The dress features a V neckline, short sleeves, and a mid-length, curve hugging fit. The ribbed knit fabric offers plenty of stretch.

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

    Style Number/Barcode: 05102-0315

    Category Name: Midi Dresses

    Price: $11.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Vibrant Side Geometric Print Bodycon Midi Dress

    Unleash your vibrant side in this stunning geometric midi dress on vacation, during weekend getaways, or at pool parties! Designed with a smooth knit fabric that effortlessly hugs your curves, it features a halter V-neck, open back, and center front slit for a trendy allure.

    Fit & Features

    • Smooth knit fabric, high stretch
    • Geometric tropical print
    • Sleeveless halter surplice V-neckline, open back
    • Ruching
    • Center front slit accent
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3929

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Mesh Muse Midi Dress

    Be a total muse in mesh with this sexy midi! The dress features a sleeveless bodice, adjustable spaghetti straps, a rounded neckline, a square back with a zipper and hook and eye closure, ruched detailing along each side, and a mid-length, flattering curve hugging fit. The garment is composed of a sheer mesh with a knit lining and features a sultry back slit.

    Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05103-0270

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Spotlight Moment V-Neck Surplice Midi Dress

    You'll love every moment in the spotlight wearing this sleeveless midi dress at parties and date nights! Boasting a surplice V-neckline and spaghetti straps, this bodycon dress accentuates your curves for a flattering look. The asymmetrical midi hem adds a touch of elegance, making it a must-have for dressy occasions. Complete the look with a clutch, heels, and earrings for a flawless finish!

    Fit & Features

    • Smooth knit fabric with stretch
    • Spaghetti straps
    • Surplice
    • Bodycon silhouette, midi-length
    • Runs true to size

    Style Number/Barcode: 05101-3028

    Category Name: Midi Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Charm Them All Midi Dress

    Charm them all in this casual yet so cute printed midi! The dress features a sleeveless bodice, spaghetti straps, a rounded neckline, and a mid-length, curve hugging fit. The dress is composed of a knit fabric with plenty of stretch.

    Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0252

    Category Name: Midi Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Foxy Lady Slinky Dress
    Hey there foxy lady we like your style! This slinky midi dress features a cowl neckline, adjustable spaghetti straps, and a square back with a hidden zipper. The dress slightly cinches at one hip and also offers a sexy side slit. The dress is composed of a smooth satin-like material that offers no stretch yet a relaxed fit. Sexy yet elegant! 

    Style Number/Barcode: 05101-0330

    Category Name: Midi Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Talk That Talk Tank Dress

    You're a bad gal, bb! Catch some eyes in this simple-yet-sexy tank dress. Including a racerback neckline that flows into a midi length, this spaghetti tank dress features a smooth, stretchy fabric that hugs your body with every move.

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

    Style Number/Barcode: 05102-0183

    Category Name: Midi Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Isn't She Lovely Lace Dress

    You're too lovely! This lace dress is ready for your next special occasion. This dress features an off-the-shoulder neckline of scalloped lace. Leading down to a ribbon bow waist, this allover lace dress is fully lined and topped with a exposed back zipper closure. Lining and lace both offer moderate amounts of stretch. Bow ribbon waist is detachable with belt loops. 

    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: 05001-0194

    Category Name: Midi Dresses

    Price: $29.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Necessary Basic Midi Dress

    Because we all need this necessary basic midi in our closet! The dress features a sleeveless bodice, spaghetti straps, a square neck and back, and a mid-length, curve hugging fit. The smooth knit fabric offers plenty of stretch for comfortable wear.

    Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0256

    Category Name: Midi Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Can't Help It Mesh Off-The-Shoulder Midi Dress

    A girl like you can't help but show up in this midi dress and slay! The midi-length dress features a sultry off-the-shoulder sweetheart neckline, short-sleeve cuffs, a ruched and padded bust, a flattering side slit, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look in strappy heels for a dinner party or wedding!

    Fit & Features

    • Off-the-shoulder sweetheart neckline
    • Short-sleeve cuffs
    • Ruched and padded bust
    • Side slit, ruched seams
    • Bodycon silhouette, midi-length hem
    • Mesh fabric, stretchy knit lining
    • Runs true to size

    Style Number/Barcode: 05101-000049

    Category Name: Midi Dresses

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK, RUST

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

  • Flatter Me Midi Dress

    No need to worry, this perfect midi will flatter your beauty! The dress features a sleeveless bodice, tank-like shoulder straps, a deep wired V neckline with seam detailing, a square back, a high waist, and a mid-length, curve hugging fit. The dress is composed of a crepe fabric, offering moderate stretch.

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

    Style Number/Barcode: 05103-0301

    Category Name: Midi Dresses

    Price: $9.97 $37.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance