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.

  • Cute And Fab Sweater Dress

    You'll look so cute and fab in this trendy sleeveless sweater dress. It features a mock neckline, a short, curve-hugging fit, and is composed of a fuzzy eyelash knit fabric. Style this dress with combat booties.

    Fit & Features

    • Sleeveless
    • Ribbed mock neckline
    • Mini-length, form-fitting silhouette
    • Eyelash knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1112

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Embrace The Chill Mock Neck Sweater Tunic

    Embrace the chill in style! This sweater tunic features a sleeveless, mock neck design on a form-fitting silhouette and mini-length hem. Composed of a soft eyelash knit fabric with a moderate stretch. Complete the look in an oversized blazer.

    Fit & Features

    • Sleeveless, mock neck
    • Form-fitting silhouette
    • Mini-length hem
    • Soft eyelash knit fabric
    • Moderate stretch
    • Fits true to size

    Style Number/Barcode: 06005-1113

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Classic Chic Vibes Mini Dress

    Elevate your everyday style with this mini dress that will give you those classic chic vibes! It features a V-neckline with a wrap-front design, shirring at the bust, flowy half-length sleeves, a cinching high waist seam, and a short, curve-hugging silhouette. Complete the look with heels and a cute clutch.

    Fit & Features

    • V-neckline, wrap-front design
    • Shirring at the bust
    • Flowy half-length sleeves
    • Cinching high waist seam
    • Mini-length, form-hugging fit
    • Knit fabric, ruched detailing
    • Runs true to size

    Style Number/Barcode: 05101-0997

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Floral Frenzy Off The Shoulder Skater Dress

    Start a frenzy with a floral dress that brings the romance! The dress features an off-the-shoulder neckline with a sweetheart bust, quarter-length short sleeves, a floral print, and a skater-length silhouette. Complete look with wedges and a floppy hat. 

    Fit & Features

    • Off the shoulder neckline
    • Sweetheart bust
    • Quarter-length short sleeves
    • Floral print 
    • Skater length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4179

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Flirty Ditsy Floral Skater Dress

    Cute and flirty, this ditsy floral skater dress is a summer staple! It features a strapless square neckline and a drop waist skater skirt silhouette. Style this dress with wedges for weekend brunch with the girls.

    Fit & Features

    • Strapless square neckline
    • Drop waist skater skirt silhouette
    • Ditsy floral print
    • Runs true to size

    Style Number/Barcode: 05102-4177

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Breaking The Rules Plaid Mini Dress

    Break the rules with a mini dress that doesn't play it safe! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, 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 thigh-high boots. 

    Fit & Features

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

    Style Number/Barcode: 05102-4168

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • First In Class Plaid Mini Dress

    Keep it classy with a plaid dress that is perf for making a stylish first impression. The dress features a sleeveless square neckline, spaghetti straps, a plaid 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 heels. 

    Fit & Features

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

    Style Number/Barcode: 05102-4169

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fun And Flirty Skater Dress

    This adorable skater dress will bring all the fun and flirty vibes to your party look! It features a sleeveless square neckline, ruffled spaghetti straps, and a cute fit and flare skater silhouette. Style this dress with hoop earrings and wedges.

    Fit & Features

    • Sleeveless square neckline
    • Ruffled spaghetti straps
    • High waist, skater silhouette
    • Cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4170

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Own That Ruched Tie Bodycon Dress
    It's time to own the night, and this bodycon dress is the way to do it! It features a stunning ruched front detail, short sleeves, and a round neckline. Slip it on with lace-up heels for total babe vibes. 

    Fit & Features
    • Short sleeves
    • Round neckline
    • Ruched front detail
    • Bodycon fit
    • Fits true to size

    Style Number/Barcode: 05102-4167

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Effortless Vibes Sleeveless Maxi Dress

    Bring on the effortless vibes this season with this pretty maxi dress! It features a sleeveless square neckline, spaghetti straps, side pockets, and a flowy silhouette with an asymmetrical hem. Cinch the dress with a belt and style it with mules for an adorable look.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Side pockets
    • Flowy, relaxed fit
    • Asymmetrical hem
    • Smooth knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4171

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

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

    You'll be the trendy member of your squad in this casual tie-dye knit mini dress. It features a sleeveless crew neckline, tank shoulder straps, an exposed seam that runs down the center, and a short, curve-hugging fit. Style this dress with booties for an edgy vibe.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Center exposed seam
    • Mini-length, form-hugging fit
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4175

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Absolute Bombshell Cutout Mini Dress

    This sultry mini dress will have you looking like an absolute bombshell! It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to a back cutout, and a mini-length, curve-hugging silhouette. Complete the look with hoop earrings.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Dual waist cutouts that lead to a back cutout
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-4166

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Stunner Cutout Midi Dress

    Stand out like the major stunner you are with a midi dress that brings the style! The dress features a plunging halter neck with a V-neck bust, a cutout at the midriff with sleek straps, and a midi-length silhouette with a high side slit. The dress is composed of a lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules. 

    Fit & Features

    • Halter neck, V-neck bust
    • Cutout at the midriff with straps
    • Midi length silhouette
    • High side slit
    • Lurex knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4157

    Category Name: Casual Dresses

    Price: $19.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • What's The Scoop Ribbed Knit Mini Dress

    Serve up a stylish look with a pretty mini dress! The dress features a sleeveless scoop neckline, a tie-front at the bust, bungee spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with plenty of stretch. Complete look with mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tie-front at the bust
    • Bungee spaghetti straps
    • Mini-length silhouette
    • Ribbed knit fabric 
    • Form-hugging fit, plenty of stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4162

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Vibes Off-The-Shoulder Floral Mini Dress

    Bring those sweet vibes with a pretty mini dress that is perf for your next date night! The dress features a ditsy floral print, an off-the-shoulder neckline, a sweetheart bust with a mini tie-front, short puff sleeves, 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

    • Off-the-shoulder neckline
    • Sweetheart bust, mini tie-front 
    • Short puff sleeves, ruffled hems
    • Mini-length silhouette
    • Brushed knit fabric, side ruched detailing
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4154

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Boho Vibes Maxi Dress

    Bring on the stunning boho vibes with this effortlessly chic maxi dress. It features a sleeveless V-neckline, spaghetti straps, a tie-front bust with a sexy waist cutout, and a curve-hugging floor-length silhouette with a sultry thigh-high side slit. Style this dress with trendy earrings and cute mules.

    Fit & Features

    • Sleeveless V-neckline
    • Spaghetti straps
    • Tie-front bust, waist cutout
    • Floor-length, form-hugging fit
    • High side slit
    • Knit fabric, paisley print
    • Runs true to size

    Style Number/Barcode: 05102-4159

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All My Love Ditsy Floral Mini Dress

    Keep it lovely and gorge with a mini dress that shows off your sweet side! The dress features a ditsy floral print, a sleeveless square neckline, spaghetti straps, a lower back keyhole with tie-back straps, and a skater silhouette with a ruffled hem. Complete look with chunky sneakers.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps 
    • Lower back keyhole
    • Tie-back straps
    • Skater silhouette, ruffled hem
    • Lightweight woven fabric, ditsy floral print
    • Relaxed fit, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4147

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cutie In Floral Puff Sleeve Mini Dress

    You'll look like such a cutie in this adorable floral mini dress! It features a subtle sweetheart neckline with a mini tie-front at the bust, short puff sleeves, and a mini-length, curve-hugging silhouette. Style this dress with your fave pair of sandals.

    Fit & Features

    • Sweetheart neckline
    • Mini tie-front at the bust
    • Short puff sleeves
    • Back zipper and hook and eye closure
    • Short, form-hugging fit
    • Floral print, knit fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4153

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sporty-Chic Knit Mini Dress

    Get a sporty-chic style with this adorable knit mini dress. It features a collared V-neckline with a zip-front, short sleeves, and a mini-length, curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with trendy mules.

    Fit & Features

    • Collared V-neckline, zip-front
    • Short sleeves
    • Mini-length hem
    • Form-hugging fit
    • Lined knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4152

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ravishing Florals Ruched Mini Dress

    Stun with ravishing florals in a pretty mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, dual ruching that runs from the bodice to hem, a ditsy floral print, 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 wedges. 

    Fit & Features

    • Sleeveless V-neckline
    • Adjustable spaghetti straps
    • Dual ruching
    • Ditsy floral print
    • Mini length silhouette
    • Lined mesh fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4151

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Baroque Bohemian Glam Mini Dress

    Stand out like the glam trendsetter you are with a mini dress that is a true one of a kind! The dress features a sleeveless cowl neckline, spaghetti straps, a bohemian paisley print with baroque-inspired accents, 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

    • Sleeveless cowl neckline
    • Spaghetti straps
    • Bohemian paisley print
    • Baroque print
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4148

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Go With The Flow Chiffon Skater Dress

    Go with the flow and keep it casual with a dress that can be dressed up or down for a date with bae. The dress features a square neckline, long balloon sleeves, an empire waist with pleating, and a skater length silhouette with a ruffled hem. The dress is composed of a lined chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with block heels and hoops. 

    Fit & Features

    • Square neckline
    • Long balloon sleeves
    • Empire waist with pleating 
    • Skater length silhouette, ruffled hem
    • Lined chiffon fabric
    • Form hugging fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05101-1133

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Shirr Thing Long Sleeve Mini Dress

    This mini dress is sure to be a hit for your closet! It features long fitted sleeves, a mock neck, and a side shirring detail that shapes the high-low short hem. The brushed knit fabric offers a moderate stretch. Style with an oversized jacket.

    Fit & Features

    • Long sleeves
    • Mock neck
    • Side shirring detail
    • Bodycon silhouette
    • High-low mini hem
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4139

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale