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.

  • All Eyes On Me Floral Eyelet Maxi Dress

    Draw all eyes on you in this bold maxi dress! The dress features a vibrant floral print, an eyelet pattern, a sleeveless V-neckline, spaghetti straps, dual waist cutouts, and a maxi-length silhouette with a flared hem. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes a mini skirt-length knit lining. Complete look with sandals and hoops. 

    Fit & Features

    • Floral print 
    • Sleeveless V-neckline, spaghetti straps
    • Dual waist cutouts
    • Eyelets
    • Maxi length silhouette
    • Lightweight woven fabric, mini skirt knit lining
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-4123

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Casual Vibes Ribbed Knit Maxi Dress

    Achieve those effortless, casual-chic vibes with this ribbed knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps, and a curve-hugging silhouette with a cute side slit to show some leg. Style this dress with sneakers for every day, or heels for date night.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Form-hugging fit
    • Side slit
    • Lined ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4118

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off To The Tropics Maxi Dress

    Head off to the tropics in a maxi dress that instantly puts you in vacay mode! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, and a maxi silhouette with 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 sandals. 

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps, cross back 
    • Tropical print
    • Maxi length silhouette 
    • High side slit 
    • Smooth knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4104

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Sweet For The Summer Babydoll Dress

    Sweet and chic, this babydoll dress is perf for the summer season. It features a square neckline, three-quarter length puff sleeves with cute ruffled hems, a high waist seam, and a short, flowy, flared-out silhouette. Style this dress with a trendy shoulder bag and mules for a weekend brunch.

    Fit & Features

    • Square neckline
    • Three-quarter length puff sleeves, ruffled elastic cinched hems
    • Stretchy smocked back detail, high waist seam
    • Mini-length silhouette
    • Flowy, flared-out fit
    • Twill fabric, woven lining, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4109

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    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
  • 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
  • Tiki Island Escape Cutout Mini Dress

    Create an island escape look with a mini dress that is perf for your next getaway! The dress features a plunging sleeveless v-neckline, halter neck ties, a sexy midriff cut-out, a tropical palm leaf print, 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.

    Fit & Features

    • Sleeveless V-neckline
    • Halter neck ties
    • Midriff cutout
    • Tropical palm leaf print
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4106

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Summer Vibes Maxi Dress

    Get those chic sultry vibes this summer in this stunning maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts, a floor-length, fitted silhouette, and an all-over tropical floral print. Style this dress with sleek hoop earrings and strappy sandals.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts
    • Floor-length, form-hugging silhouette
    • Knit fabric
    • Tropical floral print
    • Runs true to size

    Style Number/Barcode: 05102-4112

    Category Name: Casual Dresses

    Price: $6.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tropical Sunsets Asymmetrical Midi Dress

    Take in those tropical vibes with a midi dress that will have you vacay-ready! The dress features a tropical palm leaf print, a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and an asymmetrical hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and sandals. 

    Fit & Features

    • Tropical palm leaf print
    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Midi length silhouette
    • Asymmetrical hem 
    • Smooth knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4111

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sweet Ruffled Cutout Skater Dress

    Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals. 

    Fit & Features

    • Off-the-shoulder neckline 
    • Smocked bodice with a ruched drawstring
    • Long sleeves, elastic cinched hems
    • Cutout at the midriff 
    • Tiered ruffle skater skirt
    • Gauze knit fabric, relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05101-2486

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Twirl Ruffled Skater Dress

    Create a twirl-worthy moment with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a strappy back, a ditsy floral print, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with no stretch. Complete look with wedges and a clutch.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Strappy back, back zipper and hook and eye closure
    • Ditsy floral print
    • Skater silhouette 
    • Lined gauze knit fabric, relaxed fit, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4101

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrapped In Florals Chiffon Skater Dress

    Wrap yourself in a fab floral dress this season for your next brunch! The dress features a floral print, plunging V-neckline, ruffled cap sleeves, an open back with a tie-back strap, and a skater silhouette with an asymmetrical ruffled trim. The dress is composed of a semi-sheer chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with sandals and duster earrings. 

    Fit & Features

    • Wrap V-neckline
    • Ruffled cap sleeves
    • Open back with tie back ties
    • Skater silhouette
    • Ruffle trim
    • Floral print
    • Form hugging fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1103

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Own It Ribbed Knit Midi Dress

    Own your look with a ribbed dress that makes a head-turning impression! The dress features a crew neckline, long sleeves, a sexy cutout at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a teddy jacket.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Cutout at the waist
    • Midi-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1079

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Finding Inspo Scoop Neck Mini Dress

    Casual to dressy, this scoop neck mini dress is perfect for creating all sorts of stylish fits! Featuring long sleeves, a bodycon silhouette, and a slight low-back neckline on ribbed knit fabric. Complete the look in a trendy shacket and booties.

    Fit & Features

    • Long sleeves
    • Scoop neck on front and back
    • Bodycon silhouette
    • Mini-length hem
    • Ribbed knit fabric, double-lined
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4100

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Babe For The Weekend Mini Dress

    Be a bold babe in this classy stunner! This long sleeve mini dress features a wide scoop neckline on the front and back on a bodycon silhouette. Composed of a rib-knit fabric. Style with statement earrings for weekend soirees. 

    Fit & Features

    • Long sleeves
    • Wide scoop neck on the front and back
    • Bodycon silhouette
    • Mini-length hem
    • Rib-knit fabric
    • Fits true to size

    Style Number/Barcode: 05102-4099

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic And Seamless Midi Sweater Dress

    Chic and seamless, this sweater dress is perf for creating a simple yet elevated look. It features a sleeveless scoop neckline, adjustable spaghetti straps, a mid-length, curve-hugging silhouette, and a sultry thigh-high side slit. Style this dress with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Mid-length, form-fitting silhouette
    • High side slit
    • Sweater knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1085

    Category Name: Casual Dresses

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming Florals Chiffon Skater Dress

    Charm them all with a floral dress that brings those sweet vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an open-back design with cute tie-back ties, and a skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges. 

    Fit & Features

    • Floral print
    • Sleeveless V-neckline
    • Adjustable spaghetti straps 
    • Open back, tie-back ties
    • Skater silhouette
    • Chiffon fabric
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05101-1100

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    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
  • Casual Chic Cut Out Mini Dress

    Create a perf casual-chic look with this must-have mini dress. It features a sweetheart neckline, long fitted sleeves, an adjustable drawstring at the bust, a sultry waist cutout, ruching, and a short, form-hugging silhouette. Style this dress with sneakers.

    Fit & Features

    • Sweetheart neckline
    • Long fitted sleeves
    • Adjustable drawstring at the bust
    • Waist cutout, ruching
    • Mini-length, form-fitting silhouette
    • Brushed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4095

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Pull In Closer Tie Dye Mini Dress

    Pull in closer with a trendy mini dress! The dress features a tie-dye print, a crew neckline, long sleeves, ruched drawstrings, 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

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

    Style Number/Barcode: 05102-4084

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Style Icon Denim Mini Dress

    Stun like the style icon you are with a mini dress that stuns! The dress features a sleeveless sweetheart neckline, lightly padded cups, adjustable spaghetti straps, corset-like seams at the bodice, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless sweetheart neckline
    • Lightly padded cups
    • Adjustable spaghetti straps 
    • Corset-like seams at bodice
    • Mini length silhouette
    • Denim fabric 
    • Form hugging fit, moderate stretch, runs true to size 

    Style Number/Barcode: 05102-4085

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale