Casual Dresses

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.

  • Major Stunner Brushed Knit Mini Dress

    Stun like the major babe you are with a chic mini dress! The dress features a collared neckline, short sleeves, a zipper front closure, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a clear clutch.

    Fit & Features

    • Collared neckline
    • Zipper front
    • Short sleeves
    • Mini length silhouette 
    • Double-lined brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4286

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vacay Satin Ruched Tie-Back Dress

    Planning a weekend vacay? Don't forget to pack this adorable satin dress! It features spaghetti straps and a ruched bust, a mini-length hem, and an open back with self-tie detail. Complete the look chic mules.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Ruched bust
    • Mini-length hem
    • Open back with self-tie
    • Satin fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1276

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Casual Slay Ruched Midi Dress

    You'll casually slay in this basic chic midi dress with elevated details. It features a mock neckline, long fitted sleeves, a curve-hugging silhouette, and a front slit with ruching. Style this dress with trendy clear mules.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Form-fitting silhouette
    • Front slit, ruching
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4284

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty And Flowy Woven Mini Dress

    Flirty and flowy, this adorable woven mini dress is perfect for day dates! It features a V-neckline, long blouson sleeves, a high waist seam, and an A-line silhouette with tiered ruffle detailing. The lightweight woven fabric includes a knit lining. Complete the look with a denim jacket and mules.

    Fit & Features

    • V-neckline
    • Long blouson sleeves, tapered hems
    • Back zipper and hook and eye closure
    • High waist seam
    • A-line silhouette, tiered ruffle detailing
    • Woven fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4280

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Basic Mock Neck Mini Dress

    This mini dress is the perfect day-to-night style! It features long sleeves, a mock neckline, and a bodycon silhouette designed to accentuate your curves. Complete the look with a necklace.

    Fit & Features

    • Long fitted sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem 
    • Runs true to size

    Style Number/Barcode: 05102-4281

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Sassy Chiffon Mini Dress

    Sweet and sassy will be your go-to style in this adorable chiffon mini dress. It features a sweetheart neckline, a tie-front detail at the bust, long sheer bishop sleeves, a stretchy smocked back design, a short, form-hugging silhouette, and an all-over leopard print pattern. Complete the outfit with clear mules and a trendy shoulder bag.

    Fit & Features

    • Sweetheart neckline
    • Tie-front detail at the bust
    • Long sheer bishop sleeves, elastic cinched hems
    • Stretchy smocked back design
    • High waist seam, mini-length, form-fitting silhouette
    • Sheer chiffon fabric, knit lining, leopard print
    • Runs true to size

    Style Number/Barcode: 05101-1267

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Oh-So-Fab Tie-Dye Maxi Dress

    Keep your look trendy and fab in this curve-hugging tie-dye maxi dress. It features a sleeveless asymmetrical one-shoulder neckline, a single spaghetti strap, a flattering high waist seam, and a form-fitting maxi-length silhouette with a sultry thigh-high side slit. Complete the outfit with clear heels.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Single spaghetti strap
    • High waist seam
    • Maxi-length silhouette, form-hugging fit
    • High side slit, ruched detailing
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4277

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cross Out The Drama Bodycon Dress

    Cut the drama from your life in a dress that features a halter neck, cross-straps at the bodice, a sexy cutout at the midriff, a bold open back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Halter neck
    • Cross-straps at bodice
    • Cutout at the midriff
    • Open back 
    • Mini-length silhouette
    • Cotton knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4392

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring Chic Cutout Mini Dress
    Dare to go bold with a dress that is anything but basic! The dress features a collared neckline, a multi-button down front, long sleeves, dual waist cutouts, and a mini-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 heels and a crossbody. 

     

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Long sleeves
    • Dual waist cutouts
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4276

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Right Moves Ruched Mini Dress

    Make all the right moves with a mini dress that showcases your curves! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4275

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Strappy Waist Sleeveless Midi Dress

    This ribbed knit midi dress is the perf option for a casual yet still sultry look! It features a sleeveless crew neckline, tank shoulder straps, a front waist cutout with a strappy design, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Front waist cutout, strappy design
    • Mid-length, form-hugging fit
    • Side slit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4272

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Mood Tie Dye Midi Dress

    Channel a retro mood with a midi dress that is totally fab! The dress features a tie-dye print, a crew neckline, short sleeves, and a high side slit with a twist knot accent. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a denim jacket. 

    Fit & Features

    • Crew neckline
    • Short sleeves
    • High side slit, twist knot accent
    • Tie-dye pattern
    • Midi length silhouette
    • Cotton kbit fabric
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4271

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making My Mark Ribbed Mini Dress

    Make your style mark with a mini dress that is part casual, part glam! The dress features a sleeveless crew neckline, tank shoulder straps, and an open back with criss-cross straps. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Open back, criss-cross straps
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4270

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Glam Button Down Mini Dress
    Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves
    • Shoulder pads
    • Mini length silhouette
    • Lurex-knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4265

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wild At Heart Brushed Knit Leopard Mini Dress

    Showcase your wild side in a mini dress that makes a fierce impression! The dress features a leopard print, a crew neckline, long sleeves, ruched drawstrings, and a mini-length silhouette with a rounded hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto and ankle booties. 

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Ruched drawstrings
    • Leopard print
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4263

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Glam Button Down Mini Dress
    Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves
    • Shoulder pads
    • Mini length silhouette
    • Lurex-knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4264

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring Button Up Midi Dress

    Dare to button up in a midi dress that showcases your curves. The dress features a collared neckline, a button-down front, long sleeves, dual waist cutouts, and a midi-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops. 

    Fit & Features

    • Collared neckline
    • Button-down front
    • Long sleeves
    • Dual waist cutouts
    • Midi length silhouette
    • Lurex-knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4268

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

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

    Keep your everyday fall look trendy and on point with this casual-chic mini dress! It features a collared V-neckline, long fitted sleeves with slit details at the hems, a vertical seam detail running down the center with ruching, and a short, curve-hugging silhouette. Style this dress with knee-high boots.

    Fit & Features

    • Collared V-neckline
    • Long fitted sleeves, slit details at the hems
    • Vertical seam detail down the center, ruching
    • Mini-length, form-fitting silhouette
    • Knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4266

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruched Babe Long Sleeve Mini Dress

    Flaunt your figure in this crowd-pleasing mini dress featuring side ruching with ties on a form-hugging silhouette. The smooth knit fabric offers a moderate stretch. Perfect for styling with heels and a clutch. 

    Fit & Features

    • Crew neck
    • Long sleeves
    • Side ruching with ties
    • Form-hugging silhouette
    • Mini-length hem
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4259

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    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
  • 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
  • Day Dates Long Sleeve Button Down Dress

    This bodycon mini dress is totally date-worthy! It features long sleeves, a collared neckline, button-down closure with ruching, and a bodycon silhouette. The dress is composed of a soft knit fabric with a moderate stretch. Complete the look with booties and statement jewelry.

    Fit & Features

    • Long sleeves, collared neckline
    • Button-down with ruching
    • Bodycon silhouette
    • Short length hem
    • Soft knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4262

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raising The Bar Plaid Mini Dress

    Raise the bar with a mini dress that is part classy, part casual! The dress features a plaid print, a sleeveless square neckline, and a mini-length silhouette. The dress is composed of a lined knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a denim jacket. 

    Fit & Features

    • Plaid print
    • Sleeveless square neckline 
    • Mini length silhouette
    • Lined knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4256

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Plaid Mini Dress

    Look and feel like a total babe wearing this plaid mini dress! It features a sleeveless, square neckline with spaghetti straps on a form-hugging fit offering a moderate stretch. Complete your daytime look with a cropped jacket.

    Fit & Features

    • Sleeveless, square neckline
    • Spaghetti straps
    • Plaid print
    • Form-hugging fit
    • Polyester fabric with moderate stretch
    • Mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-4258

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free