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.

  • Such A Flirt Ditsy Floral Mini Dress

    Capture hearts in this flirty ditsy floral printed mini dress that is perfect for spring! It features short puff sleeves, a sweetheart neckline with a tie-front detail, and a mini-length, curve-hugging silhouette. The dress is composed of a lightweight, stretchy knit fabric with no lining. Style this floral dress with cute wedges for brunch with the girls.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Tie-front at the bust
    • Short, form-hugging fit
    • Ditsy floral print
    • Stretchy unlined knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1078

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Stylish Snake Print Ruched Mini Dress

    Keep it so stylish in a snake print mini dress that slays your night out outfits. The mini dress features a sleeveless crew neckline, a trendy snake print, ruched side seams, 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

    • Crew neckline
    • Sleeveless 
    • Snake print
    • Ruched side seams
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1077

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Rose Darling Floral and Lace Mini Dress

    Let this flirty dress showcase your sweet and sultry side for date night! The dress features a sleeveless sweetheart neckline with lace trim, sleek spaghetti straps, a disty floral print, and a stunning matching lace trim at the hem. Complete your night out look with a moto jacket and mules.

    Fit & Features

    • Sleeveless sweetheart neckline with lace trim
    • Sleek spaghetti straps
    • Ditsy floral print
    • Mini length silhouette
    • Lace hem
    • Smooth knit fabric with a knit lining
    • Form-hugging fit, moderate stretch 

    Style Number/Barcode: 05101-0940

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Basic Ribbed Knit Long Sleeve Mini Dress

    Make a sleek statement with this long-sleeve mini dress, the epitome of chic simplicity. This figure-hugging silhouette, crafted from a soft ribbed knit fabric, offers both warmth and style. Featuring a high turtleneck for a touch of polished sophistication, this mini dress is perfect for transitioning from day to evening. Layer this ribbed knit mini-dress with an oversized faux leather blazer or stylish trench coat and knee-high boots for the perfected layered outfit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Mini-length hem
    • Curve-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0703

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Ruched Snake Print Mini Dress

    You'll look so sultry and stylish in this trendy snake print mini dress. It features a V neckline, long fitted sleeves, front ruched detailing, and a short, curve-hugging fit. Pair this dress with sleek gold hoop earrings and a chic clutch for a night out.

    Fit & Features

    • V neckline
    • Long fitted sleeves
    • Front ruched detailing
    • Mini length
    • Form-hugging fit
    • Snake print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1073

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Casual-Chic Moment Maxi Dress

    Have a major casual-chic moment in this must-have maxi dress! It features short sleeves, a V neckline, and a flowy silhouette with a rounded hem and side slits. Tie the front hem in a knot to add a trendy detail. Pair this maxi dress with adorable new sandals for a laidback look.

    Fit & Features

    • Short sleeves
    • V neckline
    • Flowy silhouette
    • Rounded hem and side slits
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1072

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ready to Slay Ruched Mini Dress

    Babe, you'll be ready to slay in this sleek mini dress! Perfect for date night or a GNI, style this chic must-have with lucite heels and a sleek satin clutch. The dress features a  sleeveless crew neckline, a ruched drawstring at the side seam, 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.

    Fit & Features

    • Crew neckline
    • Sleeveless
    • Ruched drawstring
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05103-3744

    Category Name: Casual Dresses

    Price: $6.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Good Vibes Word Screen Ruched Dress

    Showcase those good vibes in this trendy ruched dress! It features tank-like shoulder straps, a round neckline, side ties, and can be worn as a mini or midi dress. The knit fabric has an all-over word screen print for a cool look. Pair this dress with chunky sneakers to keep it casual or strappy heels for an elevated 'fit.

    Fit & Features

    • Tank-like shoulder straps
    • Round neckline
    • Ruched detailing
    • Side ties at the hem
    • Word screen print
    • Knit fabric with plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-1071

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Trendy Vibes Tie Dye Mini Dress

    Get major trendy vibes in this must-have tie dye mini dress. It features long fitted sleeves, a short, curve-hugging silhouette, and has flattering ruched detailing with side ties at the hem. The dress is composed of a lightweight knit fabric with plenty of stretch. Complete your look with chunky sneakers and gold hoop earrings.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ruched detailing
    • Side ties at hem
    • Stretchy knit fabric
    • Tie dye print

    Style Number/Barcode: 05102-1070

    Category Name: Casual Dresses

    Price: $14.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sultry Style Snake Print Mini Dress

    You'll definitely have that sultry style in this trendy snake print mini dress! It features spaghetti straps, a scoop neckline, and a short, curve-hugging silhouette. Pair this dress with a faux leather jacket for a girl's night out.

    Fit & Features

    • Spaghetti straps
    • Scoop neckline
    • Short, form-hugging fit
    • All-over snake print
    • Knit fabric with moderate stretch

    Style Number/Barcode: 05102-1069

    Category Name: Casual Dresses

    Price: $19.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Play On Sleeveless Plaid Mini Dress

    Keep it playful and poised in a dress that is totally on-trend, babe! The dress features a sleeveless scoop neckline, a plaid print, and a mini length silhouette. The dress is composed of a brushed knit fabric. Complete look with ankle booties.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank-straps
    • Plaid print
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch  

    Style Number/Barcode: 05102-1067

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Button Down Chic Ribbed Mini Dress

    Button-down in this chic mini dress that is perf for grabbing coffee with your bestie. The dress features an off the shoulder neckline, long sleeves with lettuce-edge trim, a faux button-down front, 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

    • Off the shoulder neckline
    • Long sleeves with lettuce-edge trim
    • Faux button down front
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch  

    Style Number/Barcode: 06005-0896

    Category Name: Casual Dresses

    Price: $15.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Trendy Tie Dye Mini Dress

    Get an effortless and trendy look in this tie dye mini dress! It features long fitted sleeves, slashed detailing on the left side of the bodice and the right side by the bottom hem, and a neutral all-over tie dye print. Pair this dress with chunky sneakers and hoop earrings for a casual look to hang with the squad.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Slashed detailing
    • Tie dye print
    • Soft knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06002-0680

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping Knit Casual Hoodie Mini Dress

    Keep it casual in a mini dress that is part cozy and part glam. The hoodie mini dress features a corset bodice with piping detail, long sleeves, a hoodie, and a mini length silhouette. The mini dress is composed of a knit fabric that offers a form hugging fit. Complete look with chunky sneakers. 

    Fit & Features

    • Corset-like bodice with piping seams
    • Hoodie
    • Long sleeves with ribbed cuff
    • Mini length silhouette
    • Form hugging fit

    Style Number/Barcode: 06002-0670

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Tie Dye Ruched Knit Mini Dress

    Give your basic mini dress a trendy upgrade with this cute tie dye mini dress! It features short sleeves, a mini length silhouette, and drawstrings at each side with ruched detailing. Pair this dress with chunky sneakers for casual-cute vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mini length silhouette
    • Drawstrings at each side
    • Ruched detailing
    • Tie dye print
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1062

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Chic Mini Dress

    Style up this trendy mini dress for a casually chic look! It features tank-like shoulder straps, a scoop neckline, and a short, curve-hugging fit. Pair this ribbed knit dress with the matching jacket and chunky sneakers for the perf everyday 'fit.

    Shop Matching Jacket: Casually Chic Cropped Jacket

    Fit & Features

    • Tank-like shoulder straps
    • Scoop neckline
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Moderate stretch

    Style Number/Barcode: 05102-1061

    Category Name: Casual Dresses

    Price: $19.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Wrap Me In Glam Ribbed Mini Dress

    Wrap yourself in this glam sweater knit dress that brings the charm. The dress features an off-the-shoulder neckline, long sleeves, a gorge tie waist ribbon, 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 your look with mules and a trendy crossbody.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Off-the-shoulder neckline 
    • Long fitted sleeves
    • Tie waist ribbon 
    • Mini-length silhouette
    • Ribbed knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0881

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Back to Basics Knit Mini Dress

    Bring it back to basics in a dress that keeps it casual and cute. The dress features a crew neckline, long sleeves, and a mini length silhouette with a rounded hem. The dress is composed of cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with ankle booties. 

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Mini length silhouette 
    • Rounded hem 
    • Cotton knit fabric 
    • Relaxed fit 
    • Moderate stretch 

    Style Number/Barcode: 06002-0654

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Basic Ribbed Knit Mini Dress

    Rock a basic mini dress for that next coffee date with bae or layer up for a casual shopping spree. The dress features a notched V-neckline, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit that offers a moderate stretch. Complete look with ankle booties.

    Fit & Features

    • Notched V-neckline
    • Long sleeves
    • Mini length silhouette
    • Lined ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1060

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Everyday Slay Ribbed Knit Mini Dress

    Casually slay your everyday 'fit in this adorable ribbed knit mini dress! It features tank-like shoulder straps, a notch front V neckline, and a short, curve-hugging fit. Pair this dress with chunky sneakers and gold hoop earrings.

    Fit & Features

    • Tank-like shoulder straps
    • Notch front V neckline
    • Mini length silhouette
    • Form-hugging fit
    • Lined ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-1057

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pretty In Plaid Knit Mini Dress

    Get a pretty, picture-perfect look in this adorable plaid knit mini dress! It features a trendy square neckline and a short, curve-hugging silhouette. Layer on a chic jacket over this dress and style it up with heeled booties for a fall night out.

    Fit & Features

    • Spaghetti straps
    • Square neckline
    • Short, form-hugging fit
    • Allover plaid print
    • Knit fabric with plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-1049

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off The Shoulder Ribbed Cutout Mini Dress

    Stun in a mini dress that showcases curves in all the right places. Perfect for your next date night, this ribbed dress is a must! The dress features an off the shoulder neckline, fitted long sleeves, and a mid-drift cutout to show off a hint of skin. The dress is composed of a ribbed knit fabric with vertical seams that streamline the silhouette. Complete your night out outfit with hoop earrings. 

    Fit & Features

    • Off the shoulder neckline
    • Fitted long sleeves
    • Mid-drift cutout
    • Vertical seams
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0820

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keepin' Knit Cute Ruched Mini Dress

    Keep your 'fit cute and stylish in this knit mini dress! It features a crew neckline, long fitted sleeves, a high waist seam, front ruched detailing with dual adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Pair this dress with chunky sneaks for a casual feel, or dress it up with heels and a layered necklace.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • High waist seam
    • Front ruched detailing
    • Dual adjustable drawstrings at the hem
    • Short, form-hugging fit
    • Brushed knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1047

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • So Sleek Sleeveless Ruched Mini Dress

    Create a sleek impression in this mini dress to stun on your next night out! The dress features a sleeveless square neckline, tank-like straps, ruched side seams, and a mini length silhouette. Complete look with a chunky statement necklace. 

    Fit & Features

    • Sleeveless square neckline
    • Tank straps
    • Ruched side seams
    • Smooth knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1045

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance