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.

  • 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
  • Keep It Stylish Ruched Mini Dress

    Keep your 'fit stylish and on point in this curve-hugging ruched mini dress! It features long fitted sleeves, a short, form-hugging silhouette and front ruched detailing to create a flattering look. Pair this dress with heeled booties for the perf fall date night.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Front ruched detailing
    • Drawstring at front hem
    • Cotton fabric

    Style Number/Barcode: 05102-1032

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Fall Back To Basics Ribbed Knit Ruched Mini Dress

    Fall back on this basic dress to stun this season! The dress features V-neckline, long sleeves, and ruched side seams to adjust for a customized. Style your dress with ankle booties. 

    Fit & Features

    • V-neckline
    • Long sleeves
    • Ruched side seams
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-1019

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casually Slay Square Neck Ruched Mini Dress

    Casually slay in this adorable ruched dress! It features bungee spaghetti straps, a trendy square neckline, ruched side detailing, and a mini length, form-hugging silhouette to enhance your curves. Pair this dress with thigh-high boots for a majorly chic look.

    Fit & Features

    • Bungee spaghetti straps
    • Square neckline
    • Ruched side detailing
    • Mini length silhouette
    • Form-hugging fit
    • Rayon fabric with plenty of stretch

    Style Number/Barcode: 05102-1030

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Such A Sweetheart Ribbed Knit Mini Dress

    You'll look like such a stylish sweetheart in this adorable ribbed knit mini dress! It features a ruffled sweetheart neckline with a button-down front and a curve-hugging fit. Pair this cute and casual dress with some sneakers for an effortless, everyday vibe.

    Fit & Features

    • Spaghetti straps
    • Ruffled sweetheart neckline
    • Button-down front
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1016

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Angelic Beauty Ruched Mini Dress

    Look like such an angelic beauty in this gorgeous ruched mini dress! Featuring a curve-hugging fit with an allover angelic print and front ruched detailing, this dress will make you look oh so dreamy. Pair it with some clear heels for a date night.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Back zipper closure
    • Front ruched detailing with slit and drawstring accent
    • Ruffle detail at hem
    • Mesh fabric
    • Allover angelic print

    Style Number/Barcode: 05101-0914

    Category Name: Casual Dresses

    Price: $15.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Classy Shirt Dress

    This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging wrap front V neckline, long sleeves with buttons to cuff, a high waist seam, side ruched detailing, and a short fit. The dress is composed of a woven fabric with no stretch. Complete your chic look with mules and statement hoops. 

    Fit & Features

    • Collared neckline
    • Plunging v-wrap bust
    • Long sleeves with multi- buttoned cuff
    • Side ruched detailing
    • Mini length silhouette
    • Woven fabric
    • Form hugging fit, minimal stretch 

     

    Model is 5'7" with a 34" bust,  24" waist and 34" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-1015

    Category Name: Casual Dresses

    Price: $22.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

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

    Keep it retro in a tie-dye dress to brighten up your outfits! The mini dress features a mock neck with a zipper front, a tie-dye print, and a mini length silhouette complemented with ruched side seams. Complete your look with clear mules. 

    Fit & Features

    • Mock neck with zippered front
    • Long sleeves
    • Tie-dye print
    • Mini length silhouette
    • Ruched side seams
    • Form hugging fit
    • Moderate stretch 

     

    Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.

    Style Number/Barcode: 05102-1013

    Category Name: Casual Dresses

    Price: $16.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Babe Alert Snake Print Mini Dress

    Babe alert! You'll be looking majorly chic in this trendy mini dress! It features a mock neckline, long fitted sleeves with thumb holes, ruched detailing, and a short, curve-hugging silhouette. The dress is composed of a stretchy lightweight knit fabric with an allover snake print that would pair perfectly with chunky sneakers. Wear this dress to hang with the squad!

    Fit & Features

    • Mock neckline
    • Long fitted sleeves with thumb holes
    • Ruched detailing
    • Short, form-hugging fit
    • Stretchy lightweight knit fabric
    • Allover snake print

    Style Number/Barcode: 05102-1012

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming Ditsy Floral Ruffled Mini Dress

    Charm in a floral dress that brings the gorge factor for your next brunch date. The dress features a sweetheart neckline with ruffled trim, adjustable spaghetti straps, a ditsy floral print, and a mini length silhouette with a multi-tiered ruffled detail. Complete your charming outfit with wedge heels and a sleek bracelet. 

    Fit & Features

    • Sleeveless sweetheart neckline with ruffled trim
    • Adjustable spaghetti straps
    • Ditsy floral print 
    • Multi-tiered ruffled detail
    • Mini length silhouette 
    • Smocked knit fabric


    Model is 5'9" with 32" bust, 24" waist and 34" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-1009

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit Ruched Mini Dress

    This ribbed knit ruched mini dress will be a staple in your fall wardrobe! It features a curve-hugging silhouette with ruched detailing and side tie accents. It can be worn as a cute mini or pulled down as a midi dress. Pair with some bold door knocker earrings and clear heels for that chic vibe you can wear to date night.

    Fit & Features

    • High crew neckline
    • Tank-like shoulder straps
    • Form-hugging fit
    • Ruched detailing
    • Side ties at hem
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1828

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Sweet Puff Sleeve Mini Dress

    Keep your look sweet and stylish in this adorable puff sleeve mini dress! It features a tie front detail and a short, curve-hugging fit. Pair this cute dress with some strappy heels and a chic mini handbag for a brunch date with your squad.

    Fit & Features

    • Short puff sleeves
    • Sweetheart neckline
    • Tie front detail
    • Back zipper closure
    • Short, form-hugging fit
    • Woven fabric
    • Runs true to size

    Style Number/Barcode: 05102-1011

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ruffled Romance Off The Shoulder Maxi Dress

    Spark romance in a ruffled dress that is too gorgeous! The maxi dress is perfect for your next date night with bae. The dress features an alluring off the shoulder neckline, a ruffled bodice, and a tiered ruffle maxi length silhouette. Complete your stunning date night outfit with clear heels and duster earrings. 

    Fit & Features

    • Off the shoulder neckline
    • Ruffled bodice
    • Off the shoulder straps that cascade shoulders
    • Tiered maxi length silhouette, partially sheer
    • Mini skirt length knit lining
    • Lightweight woven fabric
    • Relaxed fit, minimal stretch 

    Style Number/Barcode: 05102-1007

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Best Life Square Neck Mini Dress

    Live your best life in a mini dress that can be dressed up for a night out with the squad. The dress features a sleeveless square neckline, sleek bungee straps, and a mini-length silhouette. Complete your look with sleek black heels.

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1000

    Category Name: Casual Dresses

    Price: $9.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Edgy Babe Ribbed Knit Mini Dress

    Hey babe! Showcase an effortlessly edgy style in this ribbed knit mini dress. It features a crew neckline, a chest cut out right above the bust, long fitted sleeves, and a mini length, curve-hugging silhouette. Pair this dress with combat booties for the perf look.

    Fit & Features

    • Crew neckline
    • Chest cut out
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1006

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cozy And Cute Cable Knit Mini Dress

    Get a cozy and cute look this season in this adorable cable knit mini dress! It features a wrap front and back design with a deep V-neckline, long loose sleeves with tapered hems, a tie-front waist, and a short, curve-hugging fit. Pair this dress with thigh-high boots for a date night.

    Fit & Features

    • Wrap front and back
    • V-neckline
    • Long sleeves
    • Tie-front waist
    • Mini-length silhouette, form-hugging fit
    • Cable knit fabric with moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-1003

    Category Name: Casual Dresses

    Price: $18.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Trendy Twist Knot Open Back Ribbed Mini Dress

    Stun in a dress that makes them take a double-take with bold details! The dress features a crew neckline, fitted long sleeves, and a stunning open back with a twist knot bar strap accent. 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

    • Crew neckline
    • Fitted long sleeves
    • Open back 
    • Twist knot bar strap 
    • Ribbed knit fabric
    • Mini length silhouette
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0991

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Ribbed Knit O-Ring Mini Dress

    Keep it chic in a ribbed knit dress that has a stylish twist! The mini dress features a trendy crew neckline, an O-ring accent with waist cutouts, and composed of a ribbed knit fabric that embraces curves. Complete look with clear mules for a head-turning look. 

    Fit & Features

    • Crew neckline
    • O-ring accent with waist cutouts 
    • Fitted long sleeves
    • Mini length silhouette
    • Ribbed knit fabric
    • Form-hugging fit

    Style Number/Barcode: 05102-0998

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Slay In Basics Ribbed Knit Mini Dress

    Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties. 

    Fit & Features

    • Mock neck
    • Long sleeves
    • Rounded mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 06005-0852

    Category Name: Casual Dresses

    Price: $14.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Chic Cutout Midi Dress

    Keep it chic with a midi dress that brings all the appeal. The dress features a sleeveless scoop neckline, a midriff cutout, spaghetti straps, a mini-length silhouette with a midi length overlay. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges. 

    Fit & Features

    • Sleeveless scoop neckline
    • Midriff cutout 
    • Spaghetti straps
    • Mini length silhouette with overlay
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

     

    Style Number/Barcode: 05102-0995

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • The One Basic One Shoulder Ribbed Mini Dress

    This ribbed dress is the one that you can't live without! Dress up this beauty with duster earrings and mules for a glam night out outfit. The dress features a one-shoulder neckline, a ruched mini length silhouette, and composed of a ribbed knit fabric. 

    Fit & Features

    • Sleeveless bodice
    • One-shoulder neckline
    • Ruched body
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit

    Style Number/Barcode: 05102-0997

    Category Name: Casual Dresses

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Trendy Twist Back Ribbed Knit Midi Sweater Dress

    Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Open back with twist back detail
    • Mid-length silhouette
    • Form-hugging fit
    • Ribbed sweater knit fabric

    Style Number/Barcode: 06005-0846

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance