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.

  • Feelin' Fab Tie-Dye Mini Dress

    You'll be feelin' oh-so-fab in this trendy tie-dye mini dress. It features a sleeveless scoop neckline, spaghetti straps, ruched detailing with drawstrings at the hem, and a mini-length, curve-hugging silhouette. This dress would be perf for a casual date styled with a cute crossbody purse and clear heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Ruched detailing, drawstrings at the hem
    • Short, form-hugging fit
    • Ribbed knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-1334

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • All Eyes On Me Eyelet Mini Dress

    Draw all eyes on you in this fab mini dress! The dress features a square neckline, short puff sleeves, ruching at the bodice, eyelet pattern, and a curve-hugging mini-length silhouette. The dress is composed of a lined woven fabric that offers minimal stretch. Complete look with clear mules. 

    Fit & Features

    • Square neckline
    • Short puff sleeves
    • Ruching 
    • Eyelet pattern 
    • Mini length silhouette 
    • Form hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-1291

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Effortless And Chic Eyelet Mini Dress

    Effortless and chic, this eyelet mini dress is the perfect addition to your summer wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette. Style this dress with strappy sandals.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Sheer eyelet fabric, full lining
    • Runs true to size

    Style Number/Barcode: 05102-1275

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Dare Me Denim Mini Dress

    We dare you to strut your style in this dress! The dress features a sleeveless scoop neckline, corset seams at the bust, adjustable spaghetti straps, 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 and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps
    • Corset seams the bust
    • Mini length silhouette 
    • Denim fabric 
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-1288

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Glam Ribbed Knit Maxi Dress

    Keep it casually glam with a maxi dress that is perf to dress up or down for brunch! The dress features a sleeveless V-neckline, a cute tie-front, adjustable spaghetti straps, a button-down front, and a maxi-length silhouette accented with a high center slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps, tie-front 
    • Button-down front
    • Maxi-length silhouette, high center slit
    • Ribbed knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1347

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feelin' Fierce Leopard Print Mini Dress

    You'll be feelin' fierce and fashionable in this trendy leopard print mini dress! It features a strapless sweetheart neckline with a tie-front detail, a cutout under the bust, and a short, form-fitting style to hug your curves. Complete the look with chic mules.

    Fit & Features

    • Strapless sweetheart neckline
    • Tie-front
    • Cutout under the bust
    • Mini-length, form-hugging fit
    • Smocked woven fabric
    • Leopard print
    • Runs true to size

    Style Number/Barcode: 05102-1327

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stylish Girl Summer Crochet Maxi Dress

    Keep it stylish with a crochet maxi dress that is perf for your summer adventures! The dress features a sleeveless V-neckline, a crochet waist, an open back with a crochet lace trim, and a maxi-length silhouette. The dress is composed of a woven fabric that offers a relaxed and flowy fit. Complete look with wedges and butterfly hoops.

    Fit & Features

    • Sleeveless V-neckline
    • Crochet waist
    • Open back, crochet lace trim, tie-back closure
    • Lower back hidden zipper and hook and eye closure
    • Maxi-length silhouette, relaxed fit
    • Lightweight woven fabric, short knit lining
    • Runs true to size

    Style Number/Barcode: 05102-1330

    Category Name: Casual Dresses

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • X Marks The Spot Denim Mini Dress

    Step up in a stylish denim dress that hits the style mark! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a mini side slit. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps, cross at back 
    • Mini length silhouette
    • Mini side slit
    • Denim fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-1311

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style Icon Gauze Cutout Maxi Dress

    Create a stylish moment with a maxi dress that is perf for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, a high side slit, and a maxi silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline
    • Waist cutouts with bar straps
    • Maxi silhouette
    • Gauze knit fabric
    • Relaxed fit, minimal stretch
    • Runs true to size

    Style Number/Barcode: 05102-1314

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free-spirited Floral Beauty Sleeveless Maxi Dress

    Let your natural beauty glow in this pretty maxi dress! The dress features a floral print, V-neckline, spaghetti straps that cross at the back, a lace-up back, and a high side slit. The dress is composed of an airy chiffon fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Floral print 
    • Sleeveless V-neckline
    • Spaghetti straps, cross at back 
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric, relaxed fit, runs true to size

    Style Number/Barcode: 05101-0974

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish And Lovely Eyelet Mini Dress

    Keep it stylish and lovely with a mini dress that brings sweet details! The dress features a sleeveless square neckline with a mini tie front, adjustable spaghetti straps, an eyelet pattern, and a mini-length silhouette. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Mini tie-front
    • Adjustable spaghetti straps
    • Eyelet pattern 
    • Mini length silhouette
    • Form hugging fit runs true to size

     

    Style Number/Barcode: 05102-1276

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy In Tie-Dye Satin Mini Dress

    Showcase your trendy style this summer season in this adorable satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back design, ruched detailing with side ties, a short, curve-hugging silhouette, and a fab all-over tie-dye print. Complete the look with hoop earrings and clear heels.

    Fit & Features

    • Sleeveless cowl neckline
    • Adjustable spaghetti straps
    • Cross-back design
    • Ruching, side ties
    • Mini-length, form-hugging fit
    • Satin fabric, tie-dye print, mini skirt length knit lining
    • Runs true to size

    Style Number/Barcode: 05102-1322

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sprung On You Floral Lace-Up Mini Dress

    Get sprung on this cute floral mini dress! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a cross-back lace-up back design, cute floral print, ruched side seams, and a mini-length silhouette. Complete the look with wedges and butterfly earrings for that brunch-ready look.

    Fit & Features

    • Sleeveless scoop neckline 
    • Spaghetti straps, cross at back 
    • Lace-up straps 
    • Floral print
    • Ruched side seams
    • Mini-length silhouette 
    • Smooth knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1243

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Summertime Stunner Mini Dress

    Show off your stunning style this summer in this gorg mini dress! It features a sleeveless sweetheart neckline with a ruffled trim, spaghetti straps, center ruching with a drawstring at the hem, and a mini-length, curve-hugging silhouette. Complete the outfit with cute wedges for the perfect graduation look.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Ruffled trim
    • Spaghetti straps
    • Center ruching, drawstring at hem
    • Short, form-hugging fit
    • Eyelet knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1205

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Key To Glam Greek Key Knit Dress

    Unlock your trendy style with a mini dress that stands out on your next date night! The dress features a sleeveless scoop neckline, spaghetti straps, a Greek key-inspired print, 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 clear mules. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Greek key-inspired print
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1207

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovestruck Butterfly Print Smocked Mini Dress

    Get lovestruck with this pretty butterfly print mini dress that brings the charm! The mini dress features a sleeveless sweetheart neckline with a cute tie-front accent, a cutout at the midriff, adjustable spaghetti straps, a smocked back, and a mini-length silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with mules! 

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Tie-front accent
    • Adjustable spaghetti straps 
    • Cutout at the midriff 
    • Smocked back
    • Gauze knit fabric, mini length silhouette
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1230

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fiercely Stylish Lace-Up Leopard Maxi Dress

    Keep it fiercely stylish with a maxi dress that is part bold, part glam! The dress features a leopard print, a sleeveless square neckline with racer bust, spaghetti straps, lace-up straps at back, and a flowy A-Line silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals and metal bangles. 

    Fit & Features 

    • Sleeveless square neckline
    • Spaghetti straps
    • Lace-up back 
    • A-line silhouette
    • Leopard print
    • Lightweight woven fabric 
    • Relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1195

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Rainbow Tie Dye Mesh Mini Dress

    Brighten your look with a rainbow mini dress that commands attention! The dress features a sleeveless square neckline, bungee spaghetti straps, a rainbow tie-dye hue, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Rainbow tie-dye
    • Mini length silhouette
    • Mesh fabric 
    • Form hugging fit, runs true to size 

    Style Number/Barcode: 05102-1175

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    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
  • Bombshell Babe Denim Mini Dress

    Yes babe, showcase major bombshell vibes in this stunning denim mini dress! It features a sleeveless mock neckline, tank shoulder straps with frayed detailing, a complete zip front, and a mini-length, curve-hugging silhouette. Style this dress with sneakers to keep it casually cute, or clear heels for an elevated look.

    Fit & Features

    • Sleeveless mock neckline
    • Tank shoulder straps, frayed detailing
    • Complete zip front
    • Short, form-hugging fit
    • Denim fabric
    • Runs true to size

    Style Number/Barcode: 05102-1196

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Style Tie-Front Maxi Dress

    Showcase a chic effortless style this season with this adorable maxi dress! It features a sleeveless V neckline, adjustable spaghetti straps, a tie-front detail with a small cutout, center button accents, and a flowy fit with a center slit. Pair this ribbed knit dress with a straw tote and strappy sandals.

    Fit & Features

    • Sleeveless V neckline
    • Adjustable spaghetti straps
    • Tie-front, small cutout
    • Fitted bodice
    • Center button details
    • Flowy silhouette, center slit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1174

    Category Name: Casual Dresses

    Price: $21.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Girl-Next-Door Gingham Mini Dress

    Embrace your girl-next-door vibes with this sweet mini dress! It features a sleeveless square neckline, tie shoulder spaghetti straps, a tie-front detail, and a smocked body with a mini-length, form-hugging silhouette. The woven fabric has a subtle all-over gingham print for a cute look. Complete the outfit with a denim jacket and sneakers.

    Fit & Features

    • Square neckline, ruffle trim
    • Tie shoulder spaghetti straps
    • Tie-front detail
    • Smocked body
    • Short, form-hugging fit
    • Woven fabric, gingham print
    • Runs true to size

    Style Number/Barcode: 05102-1173

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Swept Away Off-The-Shoulder Ruched Mini Dress

    Get swept away with this glam mini dress that brings chic details! The dress features an off-the-shoulder neckline with short flutter sleeves, a sweetheart bust with a drawstring, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Off-the-shoulder neckline, short flutter sleeves
    • Sweetheart bust with a drawstring
    • Ruched body
    • Mini-length silhouette
    • Lined smooth knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1167

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • The One Ribbed Knit Midi Dress

    This ribbed midi dress is the one you can't live without, bby! The dress features a sleeveless square neckline, supportive tank shoulder straps, a high side slit accented with metal snap buttons, 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 look with mules. 

    Fit & Features

    • Sleeveless square neckline
    • Tank shoulder straps
    • High side slit 
    • Snap buttons
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0955

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free