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.

  • Retro Vision Halter Striped Crochet Midi Dress

    The perfect blend of modern and retro! This halter striped crochet midi dress can easily be styled with sandals for the day and heels for night.

    Fit & Features

    • Striped design, crochet fabric, short stretchy knit lining
    • Halter neckline, spaghetti strap tie
    • Bodycon fit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-2264

    Category Name: Midi Dresses

    Price: $8.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Dreaming Of Paradise Cowl Neck Tropical Midi Dress

    Let your vacation or getaway be filled with sand and compliments when you're in this tropical midi dress! Featuring a cowl neckline and adjustable spaghetti straps for a perfect fit, this bodycon dress also boasts a side slit and midi-length hem. Complete the look with sunglasses and sandals!

    Fit & Features

    • Tropical print, stretchy knit fabric
    • Adjustable spaghetti straps
    • Cowl neckline
    • Bodycon fit
    • Side slit
    • Runs true to size

    Style Number/Barcode: 05102-5613

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Contemporary Sleek Bodycon Midi Dress

    Made in a soft rib knit fabric that snatches your figure, this sleeveless midi dress offers a contemporary and sleek style with a sleeveless square neckline and a bodycon silhouette. Pair with hoop earrings and a blazer.

    Fit & Features

    • Soft rib knit fabric, moderate stretch
    • Square neckline
    • Wide angled shoulder straps
    • Bodycon silhouette
    • Center back slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5951

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pleasant Cutie Collared V-Neck Belted Midi Dress

    Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.

    Fit & Features

    • Woven fabric with lining, no stretch
    • Collared V-neckline
    • Button-down closures
    • Adjustable belted waist with buckle
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3347

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chic Charm Striped Knit Strapless Midi Dress

    Show up with that chic charm in this striped knit midi dress designed with a strapless straight neckline and a curve-hugging bodycon fit.

    Fit & Features

    • Ribbed knit fabric, high stretch
    • Striped print
    • Strapless straight neckline
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 06005-2222

    Category Name: Midi Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless Beauty Strapless Ruffled Lace Midi Dress

    Showcase your effortless beauty in this strapless ruffled lace midi dress perfect for dressy weekend brunches! The ruched silhouette will flaunt your stunning curves.

    Fit & Features

    • Sheer lace fabric with full-length lining
    • Strapless straight neckline, ruffled overlay
    • Back zipper closure
    • Ruching
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3980

    Category Name: Midi Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Love Struck Floral Mesh Midi Tube Dress

    This midi tube dress is serving romance with a side of spice. A curve-hugging floral fit that moves with you—perfect for nights when subtle just won’t cut it.

    Fit & Features

    • Sheer mesh fabric with knit lining, high stretch
    • Floral print
    • Strapless straight-across neckline
    • Ruching
    • Back zipper closure
    • Midi-length bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-000083

    Category Name: Midi Dresses

    Price: $46.90

    Availability: In Stock

    Available Color: WINE

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

  • Cause For Celebration V-Neck Ruffle Chiffon Midi Dress

    This chiffon midi dress makes every celebration dressy and cute! With a stunning V-neckline and adjustable spaghetti straps, this flowy silhouette will flatter your figure. The tiered ruffled midi-length hem adds a touch of romance and movement to your look. Style this dress with earrings and strappy block heels.

    Fit & Features

    • Chiffon fabric lined with woven fabric
    • V-neckline
    • Adjustable spaghetti straps
    • Flowy silhouette
    • Tiered ruffled midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3354

    Category Name: Midi Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Darcy Lace-Up Glitter Lace Midi Formal Dress

    Special Occasion

    Indulge in luxurious allure in the Darcy glitter lace midi formal dress at weddings, banquets, and celebrations! She boasts a sultry plunging V-neckline, flattering padded bra cups, and adjustable spaghetti straps, this dress accentuates your figure with a form-hugging fit. The lace-up back and side slit add a touch of sensuality, while the midi-length hem and glitter lace fabric exude elegance and sophistication. Complete the look with chandelier earrings and heels!

    Fit & Features

    • Glitter lace fabric lined with stretchy knit
    • Padded bra cups
    • Adjustable spaghetti straps
    • Lace up, back zipper and hook-eye closure
    • Side slit
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05001-2129

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Soiree Hour Lace-Up Ruffled Floral Midi Dress

    When the cocktails are poured and the music starts playing it's time to unveil this floral chiffon midi dress! Perfect for daytime soirees or showers, this midi dress features a flattering scoop neckline adorned with adjustable spaghetti straps. The lace-up back and flowy ruffled silhouette offer a touch of trendiness to this midi-length dress! Complete the look with earrings and wedges.

    Fit & Features

    • Floral print, chiffon fabric lined with woven fabric
    • Scoop neckline
    • Adjustable spaghetti straps
    • Lace-up back, zipper and hook-eye closure
    • Flowy ruffled silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3411

    Category Name: Midi Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Artsy Babe Paisley Bodycon Slit Midi Dress

    Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.

    Fit & Features

    • Paisley print, mesh fabric, stretchy knit lining
    • Square neckline
    • Spaghetti straps
    • Bodycon silhouette
    • Front slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5932

    Category Name: Midi Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Arrive Like A Vision Scoop Halter Midi Dress

    Arrive like a vision in this sultry sleeveless midi dress at rehearsal dinners or a dressy date night! Crafted from a slinky knit fabric that fits like a glove, this midi-length dress exudes sophistication with a scoop halter neckline, a partially open back to show some skin and a flattering bodycon silhouette with a side slit detail for movement. Complete the look with earrings and a clutch!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Side slit
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3303

    Category Name: Midi Dresses

    Price: $19.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bria Lace And Velvet Long Sleeve Midi Dress

    Special Occasion

    Serve sultry-chic energy at your next cocktail party in the Bria formal midi dress designed with smooth velvet fabric and a sheer lace bodice. The bust includes a nude-tone lined bust with a sweetheart neckline and a velvet bow, followed by a sheer lace inset below. The dress features long fitted sleeves, a secure back zipper closure, and a midi-length bodycon silhouette accented with a stylish back slit.

    Fit & Features

    • Velvet lined fabric
    • Sheer lace bodice, nude-tone lined bust, sweetheart neckline, front velvet bow detail
    • Sheer lace inset below the bust, padded bra cups
    • Long fitted sleeves
    • High waist seam, back zipper closure
    • Midi-length bodycon silhouette, back slit
    • Runs true to size

    Style Number/Barcode: 05001-2221

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Radiate Flirtiness Halter Slit Midi Dress

    Radiate flirtiness in this sleeveless halter midi dress with a sultry V-neckline and a stunning open back with a lower ruched seam accentuating your curves. Complete the look with block heels.

    Fit & Features

    • Smooth knit fabric, sewn-in knit lining, moderate stretch
    • Halter V-neckline
    • Open back, lower ruched seam
    • Column silhouette, side slit
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3893

    Category Name: Midi Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stunning Silhouette Bodycon Midi Dress

    Show off a stunning silhouette in this sleek knit midi dress featuring a sleeveless square neck, ruching to flaunt your figure, and a hanky hem with a chic flared fit. Style with stilettos for cocktail hour!

    Fit & Features

    • Smooth knit fabric, high stretch, stretch knit lining
    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching
    • Bodycon silhouette
    • Midi-length hanky hem
    • Runs true to size

    Style Number/Barcode: 05101-4112

    Category Name: Midi Dresses

    Price: $38.90

    Availability: In Stock

    Available Color: SAGE, HUNTER, LIGHT, MARSALA, BROWN

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

  • Alianna Formal Bustier Midi Dress

    Special Occasion

    Add seriously sexy allure in the Alianna formal midi dress to spice up banquets or celebrations! She features a sweetheart bustier bodice with a built-in padded underwire bust eliminating the need for a bra, adjustable spaghetti straps, and a flattering bodycon silhouette with a side slit. The formal midi-length dress is crafted from a sleek knit-lined fabric that fits like a glove and offers plenty of stretch. Complete the look with a glam purse and lace-up heels.

    Fit & Features

    • Sleeveless sweetheart bodice
    • Built-in padded underwire bust
    • Back zipper and hook-eye closure
    • Bodycon silhouette
    • Midi-length hem, side slit
    • Sleek knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05001-1983

    Category Name: Midi Dresses

    Price: $14.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Into The Floral Forest Strapless A-Line Midi Dress

    Enchant everyone in this whimsical floral forest printed midi dress at garden parties or showers! Designed with a floral forest print on cotton woven fabric, this darling dress puts on a delightful allure. It features a strapless neckline, a stretchy smocked back, hidden side pockets for keeping your hands warm, and a flattering A-line silhouette. Complete the look in sleek stiletto heels and a purse.

    Fit & Features

    • Floral forest print, cotton woven fabric, organza lining
    • Strapless neckline
    • Smocked back
    • Hidden side pockets
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3542

    Category Name: Midi Dresses

    Price: $9.97 $64.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Glam Sophistication Sleeveless Cutout Midi Dress

    Walk into the party in this mesh sleeveless midi dress, which showcases a flirty cutout back and a form-hugging fit that flatters your figure. Complete the look with heels.

    Fit & Features

    • Mesh fabrication, stretchy knit lining
    • Sleeveless square tube neckline
    • Ruching
    • Asymmetrical layered high-slit
    • Cutout at the lower back
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3630

    Category Name: Midi Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Gorgeous In Floral Bodycon Slit Midi Dress

    Gorgeous florals flatter this chic mesh bodycon dress perfect for garden party soirees or bridal showers!

    Fit & Features

    • Floral print, mesh-lined fabric
    • Cowl square neckline
    • Adjustable spaghetti straps
    • Side ruched seams
    • Side slit
    • bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05101-3967

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Garden Of Romance Tie Back Rose Floral A-Line Dress

    Let your love bloom for this rose floral chiffon midi dress perfect for garden parties and weddings! Featuring a square neckline, adjustable spaghetti straps, and a tie-back for the perfect fit, this flowy A-line silhouette dress will have you feeling flirty and feminine. With a front slit and midi-length hem, it's perfect for styling with chic stiletto heels.

    Fit & Features

    • Rose floral print, chiffon fabric lined with stretchy knit
    • Square neckline
    • Adjustable spaghetti straps
    • A-Line silhouette
    • Front slit
    • Runs true to size

    Style Number/Barcode: 05101-3257

    Category Name: Midi Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Energy Lace-Up Bodycon Slit Midi Dress

    This floral print midi dress features a square neckline and spaghetti straps that shape the lace-up back design. The lined mesh fabric hugs your curves along the bodycon silhouette with a flirty side slit accent.

    Fit & Features

    • Floral print, mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Square neckline
    • Lace-up back
    • Side slit
    • Bodycon midi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3430

    Category Name: Midi Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tricks Of The Trade Convertible Bodycon Midi Dress

    Versatility at its finest, this sleeveless midi dress knows a trick or two! Crafted from a smooth knit fabric that fits like a glove, this dress offers a convertible neckline with a braided strap allowing for multiple styling options, side ruched seams, and a perfect bodycon fit. Complete the look with dangly earrings and heels for date night or a semi-formal event!

    Fit & Features

    • Smooth knit fabric, stretchy knit lining
    • Convertible neckline with braided strap
    • Multiple styling options, off-the-shoulder, halter, one-shoulder
    • Bodycon silhouette
    • Sticky bra or pasties recommended
    • Runs true to size

    Style Number/Barcode: 05101-3564

    Category Name: Midi Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Stroll Floral Lace-Up Midi Dress

    Soft, sultry, and effortlessly chic—this floral midi dress brings romance with every step. The strappy lace-up back and curve-skimming fit make it perfect for weddings, brunches, or dreamy date nights.

    Fit & Features

    • Floral garden print, stretch knit fabric
    • Pleated square halter neckline
    • Lace-up back detail
    • Curve-hugging fit
    • Midi-length flared hem
    • Runs true to size

    Style Number/Barcode: 05101-000388

    Category Name: Midi Dresses

    Price: $52.90

    Availability: In Stock

    Available Color: IVORY

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

  • Stop And Stun Off-The-Shoulder Midi Dress

    Create a stunning moment in a midi dress that features an off-the-shoulder neckline, short dolman sleeves, and an asymmetrical high-side slit. Complete your date night outfit with stiletto heels

    Fit & Features

    • Smooth knit fabrication, moderate stretch 
    • Off-the-shoulder neckline
    • Short dolman sleeves
    • Asymmetrical high-side slit
    • Midi length hem
    • Runs true to size

    Style Number/Barcode: 05101-3841

    Category Name: Midi Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free