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.

  • 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
  • Keeping Knit Real Ruched Mini Dress

    Keep it real in this dress that keeps it chic! The dress features a mock neck, long sleeves, ruched side seams, and a mini length silhouette. The dress is composed of knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sleek mules. 

    Fit & Features

    • Mock neck 
    • Long sleeves
    • Ruched side seams
    • Mini length silhouette
    • Knit fabric 
    • Form hugging fit 
    • Moderate stretch 

    Style Number/Barcode: 06005-0870

    Category Name: Casual Dresses

    Price: $4.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Cute and Casual Ribbed Midi Dress

    Keep it cute and casual in a knit dress that is perfect for a quick coffee run or a casual date with bae. The dress features a scoop neckline, long sleeves, a midi length silhouette, and composed of a ribbed brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers. 

    Fit & Features

    • Scoop neckline
    • Long sleeves
    • Midi length silhouette
    • Ribbed
    • Brushed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1042

    Category Name: Casual Dresses

    Price: $15.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off The Shoulder Button Down Mini Dress

    This adorable off the shoulder button down mini dress is perfect for transitioning to the cooler fall months! Featuring long fitted sleeves and a curve-hugging fit, pair this knit dress with some chunky sneakers for a trendy chic look.

    Fit & Features

    • Off the shoulder neckline
    • Long fitted sleeves
    • Button-down front
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0828

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Comfy-Chic Ribbed Knit Midi Dress

    Look so comfy-chic in this adorable ribbed knit midi dress! It features a deep V neckline, adjustable spaghetti straps, and a mid-calf length curve-hugging fit. Pair this dress under a sleek faux leather moto jacket and accessorize with a layered necklace for a date night out.

    Fit & Features

    • V neckline
    • Adjustable spaghetti straps
    • Mid-length, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1041

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Sweetheart Ribbed Knit Midi Dress

    Showcase the stylish sweetheart you are in this trendy ribbed knit midi dress! It features a sweetheart neckline with bust seam detailing, a mid-calf length and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch for comfortable wear. Pair this dress with heeled booties and layer on a faux leather jacket for an edgy vibe.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline
    • Bust seam detailing
    • Mid-length, form-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-1040

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keeping Knit Classy Sleeveless Mini Dress

    Class up your basic mini dress with details that stand out! The dress features a sleeveless crew neckline, dramatic shoulder pads, and a mini length silhouette. The dress is composed of a cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with chunky sneakers for a casual vibe.

    Fit & Features

    • Crew neck
    • Sleeveless bodice
    • Shoulder pads
    • Mini length silhouette
    • Cotton knit fabric
    • Relaxed fit
    • Moderate stretch 

    Style Number/Barcode: 05102-1033

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Better In Basics Ribbed Knit Sweater Dress

    Sometimes, basic is better, like this adorable ribbed knit sweater dress! It features a flattering V neckline, a mid-length, curve-hugging silhouette, and a front slit. Pair this sweater dress with chunky sneakers for a casual-chic vibe.

    Fit & Features

    • Thin adjustable shoulder straps with gold metal detailing
    • V neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Front slit
    • Ribbed sweater knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06005-0862

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Houndstooth Scoop Neck Mini Dress

    Stay on-trend in a mini dress that slays this season. The dress features a sleeveless scoop neckline, sleek spaghetti straps, a houndstooth print, and a mini length silhouette. Complete your look with a faux fur jacket. 

    Fit & Features

    • Sleeveless scoop neckline
    • Spaghetti straps
    • Houndstooth print
    • Mini length silhouette
    • Form hugging fit

    Style Number/Barcode: 05102-1036

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning And Sultry Sweetheart Mini Dress

    Create a stunning and sultry look in this gorgeous sweetheart mini dress! It features a sleeveless bodice with spaghetti straps, a mini length silhouette and a curve-hugging fit. Pair this dress with a faux leather jacket for a girl's night out.

    Fit & Features

    • Spaghetti straps
    • Sweetheart neckline with seam detailing at the bust
    • V back
    • Short, form-hugging fit
    • Ribbed knit fabric with plenty of stretch

    Style Number/Barcode: 05102-1039

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale