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.

  • Spotted In Style Leopard Mini Dress

    Get spotted in this mini dress that brings the bold factor to your look! The dress features a sleeveless V-neckline, bungee spaghetti straps, a leopard print, a mini side slit, and a mini-length silhouette. The dress is composed of a lightweight knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Bungee spaghetti straps 
    • Leopard print
    • Mini side slit
    • Mini length silhouette
    • Lightweight knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-2138

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Summer Romance Ditsy Floral Mini Dress

    Fall in love with this adorable ditsy floral mini dress that is perfect for summer date nights. It features short puff sleeves, a sweetheart neckline with a center criss-cross bust detail, and a mini-length, curve-hugging silhouette. Complete the outfit with a charm necklace and clear heels.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Center criss-cross bust detail
    • Short, form-hugging fit
    • Knit fabric, ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-2103

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tropical Dream Lace-Up Maxi Dress

    Get carried away in this tropical maxi dress that will have you ready for that cabana life! The dress features a tropical floral print, a sleeveless V-neckline, a double row of spaghetti straps that cross at the back, a lace-up back, and a maxi-length 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 and hoops. 

    Fit & Features

    • Tropical floral print
    • Sleeveless V-neckline
    • Double-row of spaghetti straps, cross at back
    • Lace-up back
    • High side slit
    • Maxi length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-2104

    Category Name: Casual Dresses

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Feels Ruffled Mini Dress

    This pretty floral dress has us in our feels, bby! The dress features a floral print, an off-the-shoulder neckline with a ruffled popover, ruffled short sleeves, 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 and a metal cuff. 

    Fit & Features

    • Ditsy floral print
    • Off the shoulder neckline
    • Ruffled popover, ruffled short sleeves
    • Mini length silhouette
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2096

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Floral Fever Ribbed Knit Mini Dress

    Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, 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 wedges.

    Fit & Features

    • Sleeveless sweetheart neckline
    • Spaghetti straps
    • Tie-front 
    • Ditsy floral print 
    • Mini-length silhouette 
    • Ribbed knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-2032

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Vintage Racing Sleeveless Mini Dress

    This on-trend vintage-inspired mini dress is perfect for weekend outings with the squad. It features a sleeveless scoop neckline, tank shoulder straps, and a mini-length, curve-hugging silhouette with side drawstrings at the hem. The dress has a cool center car graphic with the script "Vintage Racing." Complete the outfit with edgy combat boots.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank shoulder straps
    • Short, form-hugging fit
    • Side drawstrings
    • Car graphic with the script "Vintage Racing"
    • Runs true to size

    Style Number/Barcode: 06002-0803

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Summer Daydream Floral Mini Dress

    You'll look like such a daydream in this adorable floral mini dress. It features a sleeveless V-neckline,  bungee spaghetti straps, a mini-length fitted silhouette, and a slightly flared-out hem with a front slit. Complete the look with hoop earrings and strappy sandals.

    Fit & Features

    • V-neckline
    • Bungee spaghetti straps
    • Short, fitted silhouette
    • Slightly flared-out hem, front slit
    • Knit fabric, plenty of stretch
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-4172

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    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
  • Edgy Destruction American Motorcycle Graphic Tunic

    Channel an edgy look with a tunic that plays up your rocker side! The tunic features a V-neckline, short sleeves, eagle wings graphic, a script that reads: "American Motorcycles", destructed detailing, and a mini length. Complete look with combat boots. 

    Fit & Features

    • V-neckline 
    • Short sleeves
    • Eagle wings
    • "American Motorcycles" script
    • Destructed detailing 
    • Cotton knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 06002-0801

    Category Name: Casual Dresses

    Price: $6.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Retro Babe Sleeveless Colorblock Mini Dress

    Channel a retro moment with a mini dress that makes a stylish statement. The dress features a sleeveless crew neckline, a colorblock design accented with exposed seams, 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. 

    Fit & Features

    • Sleeveless crew neckline
    • Colorblock pattern with exposed seams
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2064

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • So Dreamy Ditsy Floral Mini Dress

    Keep it dreamy with a floral mini dress that brings the romance. The dress features a sleeveless V-neckline with a ruched center, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.

    Fit & Features

    • Sleeveless V-neckline with ruched center
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette 
    • Lined ribbed knit fabric
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-2047

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Heart Of Bloom Ditsy Floral Mini Dress

    Go full bloom with a pretty mini dress! The dress features a sleeveless square neckline, a tie-front accent, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.

    Fit & Features

    • Sleeveless sweetheart neckline 
    • Tie-front 
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette, form-hugging fit
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-2041

    Category Name: Casual Dresses

    Price: $18.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Stylish Stunner Ruched Mini Dress

    Bring stylish and stunning looks this season in this on-trend mini dress. It features a crew neckline, short sleeves, a front waist cutout with a cross-strap design, ruching, and a mini-length silhouette with ties at the hem. Pair this dress with heeled mules and a chic crossbody purse.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Front waist cutout, cross-strap design
    • Ruching
    • Short, form-hugging fit
    • Ties at the hem
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-2029

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutout Cutie Ruched Mini Dress

    Create a chic look with a mini dress that showcases your stunning style! The mini dress features a sleeveless crew neckline, a waist cutout that creates an O-ring design, a ruched drawstring, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. 

    Fit & Features

    • Sleeveless crew neckline
    • Waist cutout 
    • Ruched drawstring 
    • Mini length silhouette 
    • Smooth knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1968

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Total Knockout Knit Midi Dress

    Step up in this knockout midi dress that is all the rage! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a crew neckline, cap sleeves, and a midi-length silhouette accented with a high side slit. Elevate your look with square toe strappy mules and statement-making earrings!

    Fits & Features

    • Crew neckline
    • Cap sleeves
    • Midi length hem
    • High side slit
    • Ribbed knit fabric
    • Plenty of stretch, form-hugging fit
    • Runs true to size

    Style Number/Barcode: 06005-0897

    Category Name: Casual Dresses

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Vibes Cutout Maxi Dress

    Rock those basic vibes with a maxi dress that keeps its lowkey. The dress features a sleeveless scoop neckline, adjustable spaghetti straps, a sexy lower back cutout, and a maxi-length silhouette. The dress is composed of a lined cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with t-strap sandals. 

    Fit & Features

    • Sleeveless scoop neckline
    • Adjustable spaghetti straps 
    • Lower back keyhole
    • Maxi length silhouette with a high side slit
    • Cotton knit fabric 
    • Relaxed fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1961

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Free-Spirited Darling Tie-Dye Mini Dress

    Channel your boho side with a tie-dye dress that keeps it chic and casual. The dress features a sleeveless V-neckline with a halter neck tie, a tie-dye pattern, an open back with tie-back straps, and a mini-length A-line silhouette with tiered ruffles. The dress is composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Halter neck-tie
    • Tie-dye pattern 
    • Open back with tie back straps
    • Mini length A-line silhouette
    • Ruffles
    • Lined linen, relaxed fit, minimal stretch, runs true to size

    Style Number/Barcode: 05102-1952

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Silhouette Ribbed Knit Mini Dress

    Create a chic silhouette in this curve-hugging mini dress! It features a wrap front and back design with a V-front and back, long fitted sleeves, a high waist seam, and a mini-length fit. The ribbed knit fabric offers plenty of stretch. Style this dress with cute mules.

    Fit & Features

    • Wrap front and back, V-front and back
    • Long fitted sleeves
    • High waist seam
    • Short, form-fitting silhouette
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-0993

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off The Shoulder Ribbed Knit Mini Dress

    Button up in a chic mini dress that is perf to dress up or dress down in for your next outing! The dress features an off-the-shoulder neckline, short sleeves, a faux button-down front, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and denim jacket. 

    Fit & Features

    • Off the shoulder neckline
    • Short sleeves
    • Faux button down front
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1911

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Charm Sleeveless Mini Dress

    Bring the floral charm with a pretty mini dress! The dress features a sleeveless square neckline, smocked tie-shoulder straps, a floral print, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals. 

    Fit & Features

    • Sleeveless square neckline
    • Smocked tie-shoulder straps
    • Floral print
    • Mini length silhouette
    • Lightweight woven fabric, knit lining
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1905

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pep It Up Plaid Mini Dress

    Pep it up in a cute plaid mini dress! The dress features a sleeveless square neckline, spaghetti straps, a plaid print, 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 mules. 

    Fit & Features

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

    Style Number/Barcode: 05102-1866

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Charmer Ditsy Floral Mini Dress

    Charm them all with a mini dress that makes a sweet impression! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, 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. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Ditsy floral print 
    • Mini-length silhouette
    • Ribbed knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1895

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make It Chic Ribbed Knit Mini Dress

    Make a chic impression with a mini dress that gives off those effortlessly chic vibes! The dress features a sleeveless collared neckline, a button-down front, contrasting hued trim, 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 clear mules.

    Fit & Features

    • Sleeveless collared neckline
    • Button-down front
    • Contrasting hued trim
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0990

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Perfect Match Ponte Knit Skater Mini Dress

    This mini dress and you are a perfect match, babe! The dress features a sleeveless square neckline, spaghetti straps, tie-back straps, a lower back keyhole, and a pleated tennis-style styled skater skirt. The dress is composed of a lined Ponte knit that offers a form-hugging fit with a moderate stretch. Complete look with wedges. 

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-back straps, lower back keyhole
    • Pleated tennis skirt, skater silhouette
    • Lined Ponte knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-1863

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale