Casual Dresses

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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.

  • Stay Cozy Cable Knit Mini Dress

    Keep it cozy with a mini dress that is perf for a casual date night! The dress features a wrap V-neckline, long balloon sleeves with ribbed cuffs, a cinching tie waist with belt loops, and a mini-length silhouette. The dress is composed of cable knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties.

    Fit & Features

    • Wrap V-neckline
    • Long balloon sleeves, ribbed cuffed hems
    • Tie-waist belt with belt loops
    • Mini-length silhouette
    • Cable knit fabric 
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4250

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    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
  • Chic Silhouette Long Sleeve Maxi Dress

    Create a chic silhouette in this curve-hugging maxi dress. It features a crew neckline, long fitted sleeves, a stylish cutout at the lower back, and a floor-length form-hugging fit with a side slit. Style this dress with clear heels.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Cutout at the lower back
    • Floor-length, form-hugging fit
    • Side slit
    • Cotton fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4137

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • 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
  • Trendy Moves Mesh Mini Dress

    Make stylish trendy moves in this must-have mesh mini dress. It features a sleeveless square neckline, spaghetti straps, side ruching, and a short, curve-hugging silhouette. The sheer mesh fabric has a full knit lining and showcases an all-over subtle zebra print. Complete the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Adjustable spaghetti straps
    • Back zipper and hook and eye closure
    • Side ruching, mini-length, form-fitting silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Zebra print
    • Runs true to size

    Style Number/Barcode: 05102-4211

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Off-The-Shoulder Ribbed Knit Mini Dress

    Channel those effortless chic vibes with this sweater mini dress that slays! The dress features an off-the-shoulder neckline, a faux button-down front, long sleeves, 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 mules.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Off-the-shoulder neckline 
    • Faux button-down front
    • Long fitted sleeves
    • Lettuce edge hems
    • Mini-length silhouette
    • Ribbed knit fabric, form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1015

    Category Name: Casual Dresses

    Price: $6.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Get A Clue Plaid Blazer Dress

    Showcase a trendy look with this effortlessly fab dress that will give you an all-in-one outfit! It features a blazer-designed top with a V-neckline and a lapel collar, shoulder pads, long sleeves, a dual snap-button front, a waist cutout, and a short fitted skirt with a high waist and a faux button-down design. The plaid woven fabric has a smooth lining and no stretch. Pair this dress with strappy mules.

    Fit & Features

    • Blazer-designed top
    • V-neckline, lapel collar
    • Shoulder pads, long sleeves
    • Dual snap-button front
    • Waist cutout, hidden side zipper closure
    • Short fitted skirt, high waist, faux button-down design
    • Woven fabric, smooth lining, no stretch, plaid print
    • Runs true to size

    Style Number/Barcode: 05102-4209

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Kiss and Tell Sweetheart Cutout Midi Dress

    She’s sweet but knows how to steal the spotlight. This bodycon midi dress brings the heat with a front twist, flirty cutout, and high side slit that does the most (in the best way).

    Fit & Features

    • Rib knit fabric, sewn-in mesh lining, moderate stretch
    • Sweetheart neckline, cutout accent
    • Spaghetti straps
    • High side slit
    • Bodycon silhouette
    • Midi-length hem
    • Runs true to size

    Style Number/Barcode: 05102-000208

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Bad To The Bone Halloween Mini Dress

    Get a bad-to-the-bone spooky look with this mini dress that brings the ghoul factor to your costume! The mini dress features a mock neck, short sleeves, a skeleton graphic, 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 over-the-knee boots and adhesive face gems.

    Fit & Features

    • Mock neck
    • Short sleeves
    • Skeleton graphic
    • Mini length silhouette
    • Cotton knit fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.

    Style Number/Barcode: 05102-4247

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Street Rider Graphic Lace-Up Tee

    Show off your need for speed with a graphic tee that gives your look an edgy feel. The tee features a crew neckline, short sleeves, a graphic that reads: " The Street Riders", an image of a skull with a helmet, and a lace-up front. The tee is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Graphic: "The Street Riders"
    • Image of a skull with helmet 
    • Lace-up front
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-1024

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Hauntingly Stylish Mesh Mini Dress

    You'll look hauntingly stylish in this form-hugging mini dress! It features a sleeveless crew neckline, tank shoulder straps, and a mini-length bodycon silhouette. The sheer mesh fabric includes a full lining and showcases an all-over spiderweb print, perf for spooky season! Wear this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Short, form-hugging silhouette
    • Sheer mesh fabric, full knit lining, moderate stretch
    • Spiderweb pattern
    • Runs true to size


    Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.

    Style Number/Barcode: 05102-4141

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ride Or Die Baddie Mini Dress

    Here's looking at you baddie! Keep it bold in a mini dress that features a sleeveless scoop neckline, tank shoulder straps, a graphic that reads: "Old Motorcycle, Extraordinary Performance", an image of a motorcycle with wings, ruched drawstrings at the hem, 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 a moto jacket and ankle booties.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Graphic: "Old Motorcycle, Extraordinary Performance"
    • Image of a motorcycle with wings
    • Ruched drawstrings at hem
    • Mini length silhouette
    • Ribbed knit fabric, form-hugging fit, moderate stretch

    Style Number/Barcode: 06002-0802

    Category Name: Casual Dresses

    Price: $10.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual Fave Flowy V-Neck Midi Dress

    This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.

    Fit & Features

    • Gauze woven fabric, mini-length stretchy knit lining
    • Sleeveless V-neckline
    • Adjustable spaghetti straps, low back
    • Hidden side pockets
    • High side slit
    • Midi-length flowy silhouette
    • Runs true to size

    Style Number/Barcode: 05102-000185

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Glam Ghoul Skeleton Print Mini Dress

    Get a spooky glam look that will have your whole squad jealous in this fab mini dress! It features a sleeveless scoop neckline, spaghetti straps, a front skeleton print, and a short, form-hugging silhouette. Complete your Halloween costume with dazzling face gems and strappy heels.

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Front skeleton print
    • Mini-length, form-fitting silhouette
    • Cotton fabric, moderate stretch
    • Runs true to size


    Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.

    Style Number/Barcode: 05102-4149

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Perfect Style Plaid Mini Dress

    Showcase a chic and perfect style in this plaid mini dress that is a must-have for fall. It features a sleeveless square neckline, spaghetti straps, and a short, curve-hugging fit. Complete the outfit with a faux leather jacket to add an edgy vibe to the look.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-fitting silhouette
    • Knit fabric, moderate stretch
    • Plaid print
    • Runs true to size

    Style Number/Barcode: 05102-1864

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • So Fab Sleeveless Plaid Mini Dress

    Keep it so fab in a plaid dress that impresses! The dress features a sleeveless square neckline, spaghetti straps, a plaid 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 combat boots and layer with a long sleeve top

    Fit & Features

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

    Style Number/Barcode: 05102-4231

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Up With Knit Colorblock Mini Dress

    Keep up this season in a fab mini dress that is perf to layer on the style! The dress features a crew neckline, long sleeves, a colorblock pattern, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties!

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Colorblock pattern with exposed seams
    • Mini-length silhouette
    • Knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4300

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crazy About Ruche Collared Mini Dress

    Keep on trend with a mini dress that shows off your love for ruching! The dress features a collared neckline, a multi-button down front, long sleeves, a ruched body, and a mini-length silhouette. The dress is composed of a slinky knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Multi-button down front
    • Ruched body
    • Mini length silhouette
    • Slinky knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05101-1314

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Bring On Basics Sleeveless Midi Dress

    Bring on those basic vibes with a dress that is perf for every day! The dress features a sleeveless V-neckline, tank shoulder straps, and a midi-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 clear mules

    Fit & Features

    • Sleeveless V-neckline 
    • Tank shoulder straps
    • Midi-length silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4221

    Category Name: Casual Dresses

    Price: $32.90

    Availability: Out of Stock

    Product Badge:
    • Sale