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.

  • Hot And Cold Sweater Mini Dress

    Sweaters may be for cold weather but this mini dress is too hot not to be seen this summer! It features an off-the-shoulder neckline, short sleeve cuffs, a form-fitting silhouette, and a mini-length hem on stretchy rib-knit fabric. Complete the look in platform heels. 

    Shop More Sweater Styles: Shop The Collection

    Fit & Features

    • Off-the-shoulder neckline
    • Short sleeve cuffs
    • Form-fitting silhouette
    • Mini-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1423

    Category Name: Casual Dresses

    Price: $7.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Island Retreat Mesh Mini Dress

    Look like you're ready to jet-set off to an island retreat in this mesh mini dress! It features a sleeveless square neckline, spaghetti straps, ruched detailing down the side seams, and a short, curve-hugging fit. The lined mesh fabric features an all-over tropical palm leaf print. Complete your look with espadrille wedges.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ruching down the side seams
    • Mini-length, form-fitting silhouette
    • Tropical palm leaf print
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4534

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Light Sweater Midi Dress

    Keep your look light and effortless in this sweater midi dress perfect for any day or night summer event! It features a sleeveless, v-neck, spaghetti straps, a bodycon silhouette, and a sultry front slit. Complete the look in strappy sandals. 

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Bodycon silhouette
    • Front slit accent
    • Midi-length hem
    • Sweater rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1420

    Category Name: Casual Dresses

    Price: $16.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Cool Crew Neck Mini Dress

    Keep it cool and casual in this effortless knit mini dress for hangs with friends! It features short sleeves, a crew neck, a bodycon silhouette, and a ruched drawstring that lets you customize the style. The dress is composed of a stretchy brushed knit fabric. Complete the look in cute flat sandals.

    Fit & Features

    • Short sleeve, crew neck
    • Bodycon silhouette
    • Ruched, adjustable drawstring
    • Bodycon silhouette
    • Mini-length hem
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4856

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Take A Look Sweater Midi Dress

    Let everyone take a look at you in this sweet sweater midi dress perfect for the autumn season! This dress features a sleeveless halter neck with tie closure, a bodycon silhouette, and a cutout waist with a front slit along the hem. Complete the look in pointy-toe booties.

    Fit & Features

    • Sleeveless halter neck with tie closure
    • Bodycon silhouette
    • Cutout waist, front slit
    • Midi-length hem
    • Rib-knit sweater fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1416

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Cute Cable Knit Mini Dress

    Keep it cute and light in this cable knit mini dress perfect for a casual day date! It features a sleeveless scoop neckline, spaghetti straps, a lower back cutout, underbust trim, and a bodycon silhouette. The cable knit fabric offers a moderate stretch. Complete the look in a dainty necklace and heels.

    Fit & Features

    • Sleeveless scoop neckline, spaghetti straps
    • Lower back cutout
    • Underbust trim
    • Bodycon silhouette
    • Mini-length hem
    • Cable knit design, knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1412

    Category Name: Casual Dresses

    Price: $15.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Take Me On A Getaway Midi Dress

    Pack this alluring and chic midi dress for your next weekend getaway. It features a sleeveless halter neckline with thin straps, front ruched detailing with an adjustable drawstring, a bold front waist cutout, and a midi-length, curve-hugging fit with a high side slit. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless halter neckline, thin straps that tie at the back of the neck
    • Front ruching, adjustable drawstring
    • Front waist cutout
    • Midi-length, form-fitting silhouette, side slit
    • Ribbed sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1414

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Beachy Vibes Maxi Sweater Dress

    Bring the beachy vibes to your summer look with this effortlessly chic maxi sweater dress. It features a sleeveless scoop neckline, spaghetti straps, an open back with a cross-back strap design, and a fitted, maxi-length silhouette with a high side slit. The sweater knit fabric features pretty crochet detailing. Style this dress with sandals.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Open back, cross-back strap design
    • Fitted, maxi-length silhouette, side slit
    • Sweater knit fabric, crochet detailing, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1421

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Perfection Ribbed Knit Mini Dress

    This comfortable ribbed knit mini dress is perfect for everyday 'fits! It features a classic crew neckline, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric offers a moderate stretch. Keep it casual with sneakers and a denim jacket, or elevate the look with sleek hoops and strappy mules.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves 
    • Form-fitting silhouette
    • Mini-length hem
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1272

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cool Girl Vibes Space Dye Mini Dress

    Bring the cool girl vibes in this trendy curve-hugging mini sweater dress! It features a sleeveless halter neckline with tie-back straps, a center O-ring accent at the bust, a front waist cutout, and a fitted mini-length silhouette. The sweater knit fabric features a space dye design. Style this dress with gold hoops and cute mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Sleeveless, halter neckline, tie-back straps
    • Center O-ring accent at the bust
    • Front waist cutout under the bust
    • Short, form-fitting silhouette
    • Sweater knit fabric, moderate stretch
    • Space dye knit design
    • Runs true to size

    Style Number/Barcode: 06005-1400

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Daydream Graphic Cutout Tunic Top

    You gotta hustle girl! Work for your dreams while showcasing your edgy style in this tunic top featuring short sleeves, a V-notch neckline, and graphic front detail with side drawstring cutouts and a fitted hem. Complete the look in retro boots.

    Fit & Features

    • Short sleeves, V-notch neckline
    • Graphic front detail
    • Script reads, "Hustle Daydream"
    • Side drawstring cutouts
    • Fitted hem
    • Jersey knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-1257

    Category Name: Casual Dresses

    Price: $13.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Good Times Marble Halter Dress

    Let the good times flow in this marble print mini dress perfect for vacation and sipping mojitos! It features a sleeveless, halter neckline with a ruched drawstring and tie closure, a cutout bodice, and a form-hugging fit on the knit-lined fabric. Complete your fab look with lucite mules.

    Fit & Features

    • Halter neckline, ruched drawstring, tie closure
    • Cutout bodice
    • Form-hugging fit
    • Mini-length hem
    • Marble print knit-lined fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4531

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Animal Kingdom Zebra Satin Dress

    You'll be the head of the animal kingdom in this fierce and femme zebra satin mini dress! It features a sleek and sleeveless cowl neck, spaghetti straps, and a curve-hugging silhouette. Complete the look in strappy heels for a wild night out!

    Fit & Features

    • Sleeveless cowl neck
    • Spaghetti straps
    • Curve-hugging silhouette
    • Mini-length hem
    • Zebra pattern
    • Smooth satin with minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-4532

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Double Take Knit Mini Dress

    Wow in a mini dress that makes them all take a double take! The dress features a mock neck, long sleeves, a sexy cutout at the back, and a mini-length hem. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a trench coat. 

    Fit & Features

    • Mock neck
    • Long sleeves
    • Cutout at the back 
    • Mini length hem
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06002-1252

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Disco Diva Square Neck Mini Dress

    Get down at the disco looking like a diva in this fab retro mini dress featuring a sleeveless, square neck, bungee spaghetti straps, side ruched seams, on a knit-lined fabric with a form-hugging fit. Complete the look in platform heels for a dance party.

    Fit & Features

    • Sleeveless, square neck
    • Bungee spaghetti straps
    • Side ruched seams
    • Form-hugging fit
    • Mini-length hem
    • Retro print, knit-lined fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4529

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Spice Cutout Maxi Dress

    Sultry and spicy! Make jaws drop in this sleeveless maxi dress featuring a one-shoulder neckline, waist cutout details and a form-fitting silhouette with a high-cut side slit for a show of skin. Composed of stretchy slinky knit fabric. Finish the look in lucite mules.

    Fit & Features

    • Sleeveless, one-shoulder neckline
    • Waist cutout details
    • Form-fitting silhouette
    • High-cut side slit
    • Maxi-length hem
    • Slinky knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4528

    Category Name: Casual Dresses

    Price: $19.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty In Floral V-Neck Mini Dress

    Flirty in floral! Go forth and bloom for summer in this mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, a form-fitting silhouette, and a front slit along the hem. Complete the look in doorknocker earrings and heels.

    Fit & Features

    • Sleeveless, v-neck, bungee spaghetti straps
    • Form-fitting silhouette
    • Front slit
    • Mini-length hem
    • Ditsy floral print, stretchy knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4530

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Day Ribbed Short Dress

    Keep it casual in a cute short dress that is ready for brunch with the squad! The dress features a sleeveless V-neckline with ruching at the center, bungee spaghetti straps, and a short-length hem. 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 V-neckline 
    • Ruching at center of bodice
    • Bungee spaghetti straps
    • Short length hem 
    • Lined ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 06002-1394

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hardrock Babe Graphic Short Dress

    You're with the band. Enter backstage in this edgy babe-status graphic short dress featuring a strapless bodice, lace-up bungee straps, flexible boning inserts, side denim panels with seam detail, and a front script that reads, "Make Some Noise/ Hardrock" and a form-fitting short hem. Complete the look in a ring set.

    Fit & Features

    • Strapless tube bodice
    • Lace-up bungee straps, flexible boning inserts
    • Side denim panels, seam detail
    • A font script reads, "Make Some Noise/ Hardrock"
    • Form-fitting, short-length hem
    • Minimal stretch
    • Fits true to size

    Style Number/Barcode: 06002-1222

    Category Name: Casual Dresses

    Price: $6.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Coastal Chic Striped Mesh Tunic

    Create chic beachside looks with this on-trend mesh tunic. It features a V-neckline, long fitted sleeves with flared hems, center ruched detailing, and a short, curve-hugging fit. Style this striped tunic as a cover-up over your fave bikini.

    Fit & Features

    • V-neckline
    • Long fitted sleeves, flared hems
    • Center ruching, adjustable drawstring
    • Mini-length, form-fitting silhouette
    • Striped pattern
    • Semi-sheer mesh fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4195

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Vibes Only Ribbed Knit Mini Dress

    Rock a basic ribbed mini dress for your everyday looks! The dress features a sleeveless square neckline, bungee straps, and composed of a ribbed knit fabric. Complete look with chunky sneakers for that casual vibe. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps 
    • Ribbed knit fabric 
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06002-0638

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Mood Ribbed Knit Midi Dress

    Keep it lowkey in a dress that brings those casual vibes! The dress features a crew neckline, short sleeves, and a sexy open back with a tie-back accent. The midi dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with sneakers and a denim jacket for those girl next door vibes!

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Open back 
    • Tie-back accent
    • Midi-length, high side slit
    • Lined ribbed knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4526

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Move It To The Music Mini Dress

    Move it and groove it to the music in this sassy mini dress featuring a sleek, sleeveless, v-neck, spaghetti straps, open-back with lace-up detail, form-fitting silhouette, and a swirl print woven fabric. Complete the look in platform lucite heels.

    Fit & Features

    • Sleeveless, v-neck, spaghetti straps
    • Open-back, lace-up detail
    • Form-fitting
    • Mini-length hem
    • Swirl print, woven fabric, no stretch
    • Fits true to size

    Style Number/Barcode: 05102-4522

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Energy Marble Mesh Dress

    Radiate major stylish energy in this marble print mini dress featuring a sleek, sleeveless square neck with bungee spaghetti straps, a bodycon silhouette, and a sheer mesh overlay with lining. Complete the look braid strap mules.

    Fit & Features

    • Sleeveless, square neck, bungee spaghetti straps
    • Bodycon silhouette
    • Mini-length hem
    • Marble print
    • Sheer mesh overlay, lining
    • Fits true to size

    Style Number/Barcode: 05102-4523

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale