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.

  • Casual Trendsetter Ruched Knit Mini Dress

    Showcase casual trendsetting looks in this stylish knit mini dress. It features a square neckline, short sleeves, ruched side detailing with drawstrings, and a short, form-hugging silhouette. Pair this dress with a denim jacket and cute mules for an effortless everyday outfit.

    Fit & Features

    • Square neckline
    • Short sleeves
    • Ruched side detailing
    • Adjustable drawstrings
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4333

    Category Name: Casual Dresses

    Price: $4.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Dose Of Style Knit Mini Dress

    Serve up major style with a mini dress that is perf for a chic layered outfit. The dress features a mock neck, long sleeves, a ruched drawstring, 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 trench coat and boots. 

    Fit & Features

    • Mock neck 
    • Long sleeves
    • Ruched drawstring
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4199

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Sophisticated Collared Midi Dress

    Keep your look sleek and sophisticated in a midi dress that's a major staple! The dress features a collared neckline, long sleeves, a side slit, 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 a plaid coat and ankle booties. 

    Fit & Features

    • Collared neckline
    • Long sleeves
    • Side slit
    • Midi length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4197

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Charming Chic Ditsy Floral Mini Dress

    Bring the charm with a floral mini dress that is perf for date night! The dress features a sleeveless sweetheart neckline with a lace trim, spaghetti straps, a ditsy floral 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 wedges.

    Fit & Features

    • Sleeveless sweetheart neckline, lace trim
    • Spaghetti straps
    • Ditsy floral print
    • Mini-length silhouette, lace trim at the hem
    • Smooth knit fabric, knit lining
    • Form-hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4196

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Start A Spark Ruched Mini Dress

    Start a spark with a mini dress that showcases your luxe style! The dress features a sleeveless square neckline, bungee spaghetti straps, 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 lucite heels and gold jewelry. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4191

    Category Name: Casual Dresses

    Price: $6.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On That Retro Vibe Colorblock Mini Dress

    Channel those retro vibes with this fab mini dress! The dress features a colorblock pattern, a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, dual ruched drawstrings at the hem, 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.

    Fit & Features

    • Colorblock pattern
    • Crew neckline
    • Long sleeves
    • Cutout at midriff, criss-cross straps
    • Dual ruched drawstrings
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4192

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Essential Ribbed Knit Midi Dress

    This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Form-hugging fit
    • Side slit, midi-length hem
    • Double-lined rib knit fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4961

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Oh Snap Mock Neck Ribbed Midi Dress

    Oh, snap, imagine how cute you'd look in this ribbed midi dress! It features long sleeves, a mock neck, bodycon silhouette, and side snap-button closures on ribbed knit fabric with a moderate stretch. Complete the look in suede booties.

    Fit & Features

    • Long sleeves
    • Mock neck
    • Bodycon silhouette
    • Side snap-button closures
    • Midi-length hem
    • Ribbed knit fabric
    • Fits true to size, moderate stretch

    Style Number/Barcode: 06005-1124

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Bold Stunner Cutout Mini Dress

    Create a bold moment in a chic mini dress that stuns! The dress features a scoop neckline, short puff sleeves, dual cutouts at the waist, and an A-line silhouette. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with slides and hoops. 

    Fit & Features

    • Scoop neckline
    • Short puff sleeves
    • Dual cutouts at the waist
    • Mini length silhouette
    • Lightweight woven fabric
    • Form hugging fit, runs true to size

    Style Number/Barcode: 05102-4188

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Crochet Cutie Linen Maxi Dress

    Keep it cute in a crochet maxi dress! The dress features a sleeveless V-neckline, a lined floral lace bodice, adjustable spaghetti straps, an unlined crochet waist, and a flowy maxi-length silhouette. The dress is composed of a linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges and hoops. 

    Fit & Features

    • Sleeveless V-neckline
    • Lined floral lace bodice
    • Adjustable spaghetti straps
    • Unlined crochet waist
    • Maxi length silhouette
    • Relaxed fit, minimal stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4184

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Picture Perfect Knit Mini Dress

    Create a picture-perfect moment in a cute mini dress! The dress features a scoop neckline, spaghetti straps, an exposed seam pattern, 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 heels and hoops. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Exposed seam pattern
    • Mini length silhouette
    • Smooth knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size 

    Style Number/Barcode: 05102-4180

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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