Casual Dresses

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Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

  • Raise The Stakes High Slit Cutout Dress

    Raise the stakes in a bold maxi dress that dares to stun! The dress features a sleeveless halter neck with a racer bust, a sexy cutout at the midriff, ruching at the waist, and a high-side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops

    Fit & Features

    • Halter neck with racer bust
    • Cutout at the midriff
    • Ruching at waist
    • High side slit
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4108

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Double Take Paisley Cutout Mini Dress

    Make them take a double-take with a sexy mini dress that commands attention on your next GNO! The dress features a trendy paisley print, a halter neck, a twisted neck strap that allows you to customize the coverage of the bodice, cutout at the bodice, ruching, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Paisley print
    • Halter neck
    • Twisted neck strap, allows for adjustable coverage
    • Cutout at the bodice
    • Ruching 
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4083

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Passion For Florals Asymmetrical Mini Dress

    Show off your passion for florals with a mini dress that brings the charm! The dress features a sleeveless V-neckline, bungee straps that cross at the back, a floral print, and an asymmetrical mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Bungee straps, cross at back
    • Floral print
    • Asymmetrical mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2205

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The Minimal Satin High Slit Mini Dress

    Keep it minimal and sleek with a mini dress that is perf to dress up for your next date night! The dress features a sleeveless V-neckline, adjustable spaghetti straps, and a mini side slit. The dress is composed of a satin fabric that offers a form hugging fit with minimal stretch. Complete look with rhinestone heels and statement earrings. 

    Fit & Features

    • Sleeveless V-neckline 
    • Adjustable spaghetti straps
    • Mini side slit
    • Satin fabric, additional knit lining 
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4254

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summertime Beauty Cutout Midi Dress

    Hey beauty! Get a gorgeous look perf for summertime in this stunning midi dress. It features a sleeveless halter neckline, dual waist cutouts, and a mid-length, form-fitting silhouette to hug your curves. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless halter neckline
    • Dual waist cutouts
    • Mid-length, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4255

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Beach Goddess Crochet Lace-Up Maxi Dress

    She’s giving beach goddess vibes from brunch to golden hour cocktails. This crochet maxi hugs your curves with a bodycon fit and an open lace-up back that’s totally Insta-worthy.

    Fit & Features

    • Crochet lined fabric
    • V-neckline
    • Spaghetti straps
    • Open lace-up back design
    • Bodycon silhouette
    • Maxi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000072

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Feels Ruffled Mini Dress

    This pretty floral dress has us in our feels, bby! The dress features a floral print, an off-the-shoulder neckline with a ruffled popover, ruffled short sleeves, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a metal cuff. 

    Fit & Features

    • Ditsy floral print
    • Off the shoulder neckline
    • Ruffled popover, ruffled short sleeves
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2096

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Go With The Flow Smocked Maxi Dress

    Go with the flow in a casual maxi dress that keeps your look effortlessly chic! The dress features a sleeveless square neckline, a smocked bodice, halter neck ties, a triple-row bar strap design, and a flowy maxi length silhouette. The dress is composed of a lined gauze fabric that offers a relaxed fit with slight stretch. Complete look with wedges and a floppy hat

    Fit & Features

    • Sleeveless square neckline
    • Smocked bodice
    • Halter neck ties
    • Triple-row bar strap
    • Maxi length silhouette
    • Lined gauze knit fabric
    • Relaxed fit, slight stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1362

    Category Name: Casual Dresses

    Price: $6.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Radiance Eyelet Mini Dress

    Radiate in a gorge floral mini dress for your next brunch date! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of an eyelet knit fabric that offers a form hugging fit with minimal stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Mini length silhouette
    • Eyelet knit fabric 
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4091

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Crochet Cutie Linen Maxi Dress

    Keep it cute in a crochet maxi dress! The dress features a sleeveless V-neckline, a lined floral lace bodice, adjustable spaghetti straps, an unlined crochet waist, and a flowy maxi-length silhouette. The dress is composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Lined floral lace bodice
    • Adjustable spaghetti straps
    • Unlined crochet waist
    • Maxi length silhouette
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4184

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Wonder Ruffled Skater Dress

    Make em' awestruck with a pretty mini dress! The dress features a floral print, an off-the-shoulder neckline, ruffled off-the-shoulder straps, a mini tie-front accent at the bust, a smocked bodice, a tie waist belt, and a skater silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with wedges and butterfly earrings. 

    Fit & Features

    • Floral print
    • Off the shoulder neckline with ruffled shoulder straps
    • Smocked bodice, mini-tie front 
    • Tie waist belt
    • Skater silhouette
    • Chiffon fabric
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4227

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Knit Mini Dress

    Create a picture-perfect moment in a cute mini dress! The dress features a scoop neckline, spaghetti straps, an exposed seam pattern, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with heels and hoops

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Exposed seam pattern
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-4180

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Trendy Cutout Mini Dress

    Keep your look trendy and chic in this ribbed knit mini dress that is a summer staple! It features a sleeveless crew neckline, a front O-ring accent, dual waist cutouts, and a short, curve-hugging silhouette. Style this dress with sneakers for everyday wear, or cute mules for date night.

    Fit & Features

    • Sleeveless crew neckline
    • Front O-ring detail
    • Dual waist cutouts
    • Mini-length, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4115

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simple And Sexy High-Slit Midi Dress

    Simple and sexy, this ribbed cotton midi dress can be dressed up or down. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, a high side slit, and a mid-length, curve-hugging silhouette. Style this dress with sandals to keep it casual, or heels for a chic vibe.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, cross-back design
    • High side slit
    • Mid-length, form-hugging fit
    • Ribbed cotton fabric, lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4213

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortlessly Chic Smocked Maxi Dress

    Capture those effortlessly chic vibes in this maxi dress! The dress features a square neckline, short sleeves, and a smocked bodice. The maxi length silhouette features a button-down center and a mini skirt length lining. The dress is composed of a smocked knit fabric and lightweight woven fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a floppy hat

    Fit & Features

    • Square neckline, short sleeves
    • Smocked bodice
    • Button-down center
    • Maxi length silhouette
    • Mini skirt length knit lining
    • Smocked knit, lightweight woven fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4113

    Category Name: Casual Dresses

    Price: $19.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summer Romance Asymmetrical Mini Dress

    Fall in love with this dreamy tropical printed mini dress that is a must-have for summer vacays. It features a sleeveless V-neckline, adjustable spaghetti straps, side ruched detailing, and a mini-length, curve-hugging silhouette with a trendy asymmetrical hem. Style this dress with cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Side ruched detailing
    • Short, form-hugging fit
    • Asymmetrical hem
    • Brushed knit fabric, plenty of stretch, tropical palm leaf print
    • Runs true to size

    Style Number/Barcode: 05102-1857

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this pretty mini dress! The dress features a sleeveless square neckline, spaghetti straps, a ruched mini length with drawstring, and an eyelet pattern throughout. The dress is composed of a lined lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and a straw tote

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruched drawstring
    • Eyelet pattern
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1381

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Put A Ring On It Cutout Mini Dress

    Put a ring on this cute mini dress that is a must for your next night out! The dress features a plunging sleeveless V-neckline, dual cutouts at the waist, an O-Ring at the center of the bodice, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless V-neckline
    • Cutouts at the waist
    • O-Ring
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2139

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sunset Vibes Sleeveless Mini Dress

    Showcase a gorgeous glow in this sunset-hued tie-dye mini dress! It features a sleeveless scoop neckline, tank shoulder straps, and a short, curve-hugging silhouette. The brushed knit fabric offers plenty of stretch. Style this dress with a denim jacket and sneakers for a casual look.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mini-length, form-hugging fit
    • Brushed knit fabric, plenty of stretch
    • Tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1483

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sheer Appeal High Slit Halter Dress

    Bring some serious sheer appeal with a maxi dress that wows! The dress features a halter neck with a plunging keyhole, halter neck tie, and a maxi-length silhouette with a high side slit. The dress is composed of a sheer mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a chic updo. 

    Fit & Features

    • Halter neck 
    • Plunging keyhole 
    • Halter neck tie
    • Maxi length silhouette
    • High side slit
    • Mesh fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-1203

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get It Girl Belted Skater Dress

    Get a bold style in this belted skater dress! The fitted waist belt and seam details accentuate your silhouette, while the pleated skirt adds movement.

    Fit & Features

    • Twill stretch fabric, stretchy knit lining
    • Strapless neckline with grommet trim
    • Back zipper and hook-eye closure
    • Seam detailing
    • Belted waist
    • Skater silhouette, pleated mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000105

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Color Burst Tie Dye Mini Dress

    Add a burst of color to your look with this fab mini dress! The dress features a tie-dye print, sleeveless square neckline, bungee straps that cross at the back, lace-up straps, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps, cross at the back 
    • Lace-up straps 
    • Mini length silhouette
    • Tie-dye print
    • Smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4114

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The One Eyelet Mini Dress

    This eyelet dress is the one for you, babe! The dress features an eyelet pattern, a scoop neckline with a tie-bust accent, spaghetti straps, ruffle trim at the bodice, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges

    Fit & Features

    • Sleeveless scoop neckline, tie-bust accent
    • Spaghetti straps
    • Ruffle trim at bodice
    • Mini length silhouette
    • Eyelet pattern
    • Lightweight woven fabric, lined knit fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4122

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Daydream Mesh Mini Dress

    You'll look like such a daydream in this trendy tie-dye mini dress! It features a sleeveless scoop neckline, spaghetti straps, a twist-back design, a short, curve-hugging silhouette, and a subtle all-over tie-dye print in pretty pastel hues. Style this dress with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Twist-back design
    • Mini-length, form-hugging fit
    • Mesh fabric, tie-dye print, pastel hues
    • Runs true to size

    Style Number/Barcode: 05102-4131

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale