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.

  • 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:
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  • 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:
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  • 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
  • Basic Must-Have Midi Sweater Dress

    This basic midi sweater dress is a must-have in your wardrobe. It features a sleeveless scoop neckline, tank shoulder straps, a mid-length, curve-hugging silhouette, and a ribbed sweater knit fabric that offers a moderate stretch. Style this dress with chic mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Mid-length, form-hugging fit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0958

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Making Moves Sleeveless Mini Dress

    Make stylish moves in this LBD that stuns! The dress features a halter neck with a halter neck strap, a partially open back, and a mini-length silhouette. Complete look with rhinestone heels and a rhinestone bracelet.

    Fit & Features

    • Halter neckline
    • Halter neck strap
    • Triangle-shaped bodice
    • Partially open back 
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0962

    Category Name: Casual Dresses

    Price: $14.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Too Chic Ruffled Eyelet Mini Dress

    You'll be looking too chic with a mini dress that brings all those cute deets! The dress features an elastic square neckline, short puff sleeves, a lace-up front, an eyelet design, and a mini-length silhouette with a ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.

    Fit & Features

    • Elastic square neckline, puff short sleeves
    • Front lace-up 
    • Form-fitting, mini-length, ruffle hem
    • Eyelet lace fabric, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1163

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Feeling Sweet And Stylish Eyelet Mini Dress

    Channel a sweet look with a floral dress that makes a flirty impression. The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print with eyelets, and a mini-length silhouette. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Eyelets
    • Mini length silhouette
    • Lightweight woven fabric, relaxed fit, runs true to size

    Style Number/Barcode: 05102-1130

    Category Name: Casual Dresses

    Price: $6.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All My Heart Ruched Mini Dress

    Give all your love with this fluttery mini dress! The dress features an off the shoulder neckline with a sweetheart bust, a fab lace-up front, off the shoulder flutter sleeves, and a ruched body. The dress is composed of a double-lined cotton-blend fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Off the shoulder neckline
    • Lace-up front
    • Off the shoulder flutter sleeves
    • Ruched body
    • Mini length silhouette
    • Double-lined cotton blend fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-1124

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fab And Retro Tie-Dye High Slit Maxi Dress

    Keep it fab with a dress that channels a retro feel! The maxi dress features a sleeveless scoop neckline, spaghetti straps, a tie-dye print, a high side slit, and a maxi length silhouette. The dress is composed of a ribbed kit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti strap
    • Tie-dye print
    • High side slit
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1122

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Drawn To You One-Shoulder Mini Dress

    Everyone will be drawn to you in this chic one-shoulder mini dress! It features stylish ruched detailing, a drawstring at the hem, and a short, curve-hugging silhouette. Pair this dress with clear heels and a sleek clutch for your next night out.

    Fit & Features

    • Sleeveless one-shoulder neckline
    • Ruched detailing
    • Drawstring at the hem
    • Mini-length, form-hugging fit
    • Lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05103-3784

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet And Chic Ruched Knit Mini Dress

    Keep your style sweet and chic in this adorable ruched knit mini dress! It features a sweetheart neckline with a mini keyhole cutout and tie at the bust, short sleeves, ruching down the sides, and a short, curve-hugging silhouette. Complete your look with wedges and a cute handbag.

    Fit & Features

    • Sweetheart neckline
    • Mini keyhole cutout and tie at the bust
    • Short sleeves with cinched hems
    • Ruching
    • Mini-length, form-hugging fit
    • Lined stretchy knit fabric

    Style Number/Barcode: 05102-1123

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sleek Asymmetric Maxi Dress

    Keep your look sleek and on-trend with this chic sweater maxi dress. It features a one-shoulder neckline with a tank shoulder strap and a curve-hugging maxi silhouette with a dramatic asymmetric hem creating a sultry side slit. Pair this sweater knit dress with clear heels and a new purse. 

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • One-shoulder neckline
    • Tank shoulder strap
    • Form-hugging maxi silhouette
    • Asymmetric hem creating a side slit
    • Sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1295

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Boho-Chic Crochet Midi Dress

    Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Mid-length, form-hugging fit
    • Sheer crochet fabric, fringe hem
    • Runs true to size

    Style Number/Barcode: 06005-0949

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
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  • Stylish Basics Sleeveless Midi Dress

    Keep it stylish with a midi dress that can be dressed up! The dress features a sleeveless V-neckline, spaghetti straps, 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 clear mules and a metal cuff.

    Fit & Features 

    • Sleeveless V-neckline
    • Spaghetti straps
    • Midi-length silhouette 
    • Ribbed knit fabric 
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0947

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Twist Ribbed Knit Midi Dress

    Give your midi dress a stylish twist with chic details! The dress features a sleeveless crew neckline, a twist knot accent at the back with a lower back keyhole, 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 crew neckline
    • Twist knot accent at back
    • Lower back keyhole
    • Midi length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-0942

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Set It Off Ruched Mini Dress

    Set off your look with a dress that showcases your luxe style! The dress features a sleeveless square neckline, tank straps, a ruched side seam, 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 mules. 

    Fit & Features

    • Sleeveless square neckline
    • Tank straps
    • Ruched side seam 
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1120

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free