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.

  • Brushed Knit Sleeveless Crew Neck Midi Dress

    Slip into this adorable sleeveless midi dress for a chic everyday look! It features a crew neckline and a mid-calf length, curve-hugging silhouette. The brushed knit fabric has a soft cashmere-like feel. Pair this dress with chunky sneakers for a casual vibe or heeled booties for a date night.

    Fit & Features

    • Crew neckline
    • Tank-like shoulder straps
    • Mid-length, form-hugging fit
    • Brushed knit fabric

    Style Number/Barcode: 05102-0984

    Category Name: Casual Dresses

    Price: $15.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sleeveless Shaggy Knit Mini Dress

    Keep it chic in a shaggy knit dress that brings flair to your wardrobe. The dress features a sleeveless scoop neckline, tank straps, and a mini length silhouette. The dress is composed of an unlined shaggy knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.

    Fit & Features

    • Sleeveless scoop neckline
    • Tank straps
    • Mini length silhouette
    • Shaggy knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0982

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Need For Basics Ribbed Midi Dress

    Get your need for basics in a dress that can be dressed up or dressed down for your next day out. The dress features a trendy square neckline, tank-like straps, and a midi length silhouette. Complete your look with clear heels and statement hoop earrings. 

    Fit & Features

    • Sleeveless square neckline
    • Tank-like straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit 

    Style Number/Barcode: 05102-0871

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stylish Babe Scoop Neck Mini Dress

    You'll be a total stylish babe in this chic mini dress! It features a wide scoop neckline, long fitted sleeves, and a curve-hugging, mini length silhouette. The dress is composed of a brushed knit fabric with plenty of stretch for comfortable wear. Pair this dress with thigh-high boots to elevate it to a night out look!

    Fit & Features

    • Wide scoop neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Brushed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-0986

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Tied to Basics Ribbed Knit Scoop Neck Mini Dress

    Get tied to basics in a ribbed mini dress that is oh too gorgeous! The dress features a scoop neckline, tie spaghetti straps, and composed of a ribbed knit fabric that hugs curves in all the right places. Complete your casually cute look with stud earrings and block heels.

    Fit & Features

    • Scoop neckline
    • Tie spaghetti straps
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch

    Style Number/Barcode: 05102-0978

    Category Name: Casual Dresses

    Price: $7.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Basic Side Slit Ribbed Knit Mini Dress

    Amp up your basic mini dress with a trendy side slit! This staple piece dress features a mock neck, long sleeves, and a side slit. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.

    Fit & Features

    • Mock neck
    • Long sleeves
    • Side slit
    • Mini length silhouette
    • Lined ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0966

    Category Name: Casual Dresses

    Price: $16.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Gorgeous Girl Faux Wrap Front Ribbed Mini Dress

    You'll look oh so gorgeous in this wrap front ribbed mini dress! Featuring a deep V neckline and a ribbed knit fabric that will hug your curves, this dress is perf for a night out. Pair with some large hoop earrings and heels to complete the vibe.

    Fit & Features

    • Bungee spaghetti straps
    • Deep V neckline
    • Faux wrap front with asymmetric hem
    • Ruched detailing
    • Short, form-hugging fit
    • Ribbed knit fabric


    Model is 5'8" with a 32" bust,  23" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0818

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back Ruched Ribbed Knit Midi Dress

    Style up this basic ribbed knit midi dress for the perfect everyday look! It features a partial lower open back, ruched detailing and a curve-hugging mid-length silhouette. Pair the dress with chunky sneakers to get that casual, cute vibe.

    Fit & Features

    • Scoop neckline
    • Long fitted sleeves
    • Partial lower open back
    • Ruched detailing
    • Form-hugging fit
    • Midi length
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0977

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Major Crush Cozy Mini Dress

    You'll absolutely love this cozy crush-worthy mini dress! It features an off the shoulder fold-over neckline, long blouson sleeves with tapered hems, and a mini length, curve-hugging silhouette. The lightweight knit fabric has a cashmere-like feel and offers plenty of stretch. Pair this dress with thigh-high boots for the perf holiday look.

    Fit & Features

    • Off the shoulder fold-over neckline
    • Long blouson sleeves
    • Short, form-hugging fit
    • Soft knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-0970

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Stunning Mesh Mini Dress

    Keep it Stunning in a chic mini dress, babe! The dress features a sleeveless square neckline, bungee-corded straps, and a curve-hugging mini-length silhouette. Complete the look with chic mules.

    Fit & Features

    • Sleeveless square neckline
    • Corded shoulder straps 
    • Mini-length silhouette
    • Sheer mesh fabric, full knit lining
    • Form-hugging fit
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-0976

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keepin' Knit Chic Midi Sweater Dress

    Keep it chic and stylish in this knit midi sweater dress, a perf transitional piece into the new season! It features a curve-hugging fit and a mid-length silhouette. Pair the dress with some trendy heeled booties for that must-have fall look.

    Fit & Features

    • V neckline
    • Tank-like shoulder straps
    • Mid-length silhouette
    • Form-hugging fit
    • Ribbed sweater knit fabric

    Style Number/Barcode: 06005-0832

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cut To The Chase Knit Mini Dress

    Let's cut to the chase - this knit mini dress is so chic! Featuring trendy cut outs and a sexy, curve-hugging fit, this dress is perf for a girl's night out. Pair it with chunky gold hoops to give the look some glam.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Waist cut out
    • Ruched detailing
    • Short, form-hugging fit
    • Knit fabric with plenty of stretch

    Style Number/Barcode: 05102-0974

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Own Knit Ruched Mini Dress

    Own your gorgeous look in this adorable knit mini dress! It features a trendy mock neckline, ruched detailing down the back, and a sexy curve-hugging fit. Pair this dress with some chic heels for a night out.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Open back
    • Ruched back detailing
    • Short, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0971

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Slaying Knit Sleeveless Ribbed Midi Dress

    Slay it in a ribbed knit dress that stuns for your next date night in! The dress features a sleeveless square neckline, sleek bungee straps, and a curve-hugging midi-length silhouette. Complete look with clear mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Midi length silhouette
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0964

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Every Day Ribbed Knit Midi Dress

    This knit dress is perfect for your everyday occasions! Layer with chunky sneakers and dainty rings to create a chic back to school outfit this season. The dress features a mock neck, long sleeves, a midi-length silhouette, and composed of a soft to the touch ribbed knit fabric that enhances curves.

    Fit & Features

    • Mock neck 
    • Long sleeves
    • Midi length silhouette
    • Lined ribbed knit fabric
    • Form hugging fit
    • Moderate stretch 

    Style Number/Barcode: 05102-0960

    Category Name: Casual Dresses

    Price: $12.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Flowy Floral Woven Midi Dress

    Create an effortlessly pretty look in this floral woven midi dress! It features a trendy tie front detail and a flattering flowy mid-length silhouette. Pair the dress with block heels and gold hoops for the perfect date night outfit.

    Fit & Features

    • V neckline
    • Tie front detail
    • Three-quarter length flowy sleeves
    • Front waist cut out
    • Mid-length flowy fit
    • Floral printed woven fabric

     

    Model is 5'7" with a 32.5" bust, 24" waist and 34" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0962

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Casual Vibes Button Down Ribbed Mini Dress

    Rock a basic mini dress to layer with your favorite denim jacket or moto jacket this season. The dress features a crew neckline, a button-down front, long sleeves, and a mini length silhouette with a raw edge hem. The dress is composed of a ribbed knit fabric.

    Fit & Features

    • Crew neckline
    • Button-down front
    • Long sleeves
    • Mini length silhouette, raw edge hem
    • Ribbed knit fabric
    • Form hugging fit
    • Moderate stretch

    Style Number/Barcode: 05102-0955

    Category Name: Casual Dresses

    Price: $10.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Keep It Chill Off The Shoulder Mini Dress

    Keep your look casual and chill but still cozy for the cooler months in this off the shoulder mini dress! It features long fitted sleeves, a short, form-hugging fit, and a soft, cashmere-like fabric that offers plenty of stretch. Pair this dress with chunky sneakers for an adorable everyday look.

    Fit & Features

    • Off the shoulder fold-over neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Soft brushed knit fabric with plenty of stretch
    • Stretchy knit lining

    Style Number/Barcode: 05102-0951

    Category Name: Casual Dresses

    Price: $13.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

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

    Being basic isn't a bad thing babe! Style up this essential ribbed knit mini dress for a cute everyday look. It features a mock neckline, long fitted sleeves, and a short, curve-hugging silhouette. The ribbed knit fabric has a soft, cashmere-like feel and offers plenty of stretch. Pair this dress with chunky sneakers for a casual vibe.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Mini length silhouette
    • Form-hugging fit
    • Brushed ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 05102-0947

    Category Name: Casual Dresses

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All Dolled Up Ribbed Knit Mini Dress

    Get dolled up in a dress that is oh so stylish! Perf for date night, the dress features a mock neck, long Dolman sleeves, 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 thigh-high boots and hoops. 

    Fit & Features

    • Mock neck 
    • Long Dolman sleeves
    • Mini length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit 
    • Moderate stretch 

    Style Number/Barcode: 06005-0823

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ribbed Knit Tie-Front Mini Sweater Dress

    Wrap yourself in the cozy elegance of this long-sleeve mini sweater dress. The dress features a flattering wrap design with a side tie that cinches at the waist, enhancing your silhouette. Crafted from a soft ribbed knit fabric, it offers both warmth and style, making it perfect for chilly days. The plunging V-neckline adds a touch of allure, while the Dolman-shaped sleeves maintain a chic and sophisticated look. Ideal for any autumn or winter occasion, this sweater dress pairs beautifully with boots or heels for a stylish seasonal ensemble.

    Shop More Sweater Dresses: Sweater Dress Collection

    Fit & Features

    • Wide V-neckline
    • Long sleeves
    • Backstrap accent
    • Wrap front and back
    • High waist seam with tie-front detail
    • Short, form-hugging fit
    • Ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06005-1555

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Babe Off The Shoulder Sweater Dress

    Showcase your major babe status in this chic sweater dress! It features an off the shoulder neckline with a fold-over detail, long fitted sleeves, and a mini length, curve-hugging silhouette. Pair this dress with thigh-high boots for an adorable date night look.

    Fit & Features

    • Off the shoulder neckline
    • Fold-over detail
    • Long fitted sleeves
    • Short, form-hugging fit
    • Angora knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06005-0811

    Category Name: Casual Dresses

    Price: $17.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feeling Knit Crew Neck Midi Dress

    Fall for a knit dress to usher in those cozy vibes this season! The dress features a crew neckline, short sleeves, and is composed of a textured knit fabric with a moderate stretch. The dress offers a form-hugging fit. Complete the look with ankle booties.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Midi-length silhouette 
    • Textured knit fabric with knit lining
    • Moderate stretch
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-0941

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sassy Snake Print Ruched Mini Dress

    Keep it sassy in a snake print mini dress that hypnotizes them all. The dress features a sleeveless square neckline, a trendy snake print, ruched side seams, and a mini length silhouette. Pair your dress with chic hoops and a cute wristlet. 

    Fit & Features 

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

    Style Number/Barcode: 05102-0945

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale