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.

  • 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
  • Sporty-Chic Long Sleeve Mini Dress

    Give your everyday look a sporty-chic vibe by styling up this adorable mini dress! It features long fitted sleeves, a mock neckline with a partial zip front, and a short, form-hugging fit. Pair this dress with chunky sneakers to casually slay your 'fit!

    Fit & Features

    • Long fitted sleeves
    • Mock neckline
    • Partial zip front
    • Mini length
    • Curve-hugging silhouette
    • Double-lined brushed knit fabric
    • Plenty of stetch

    Style Number/Barcode: 05102-0930

    Category Name: Casual Dresses

    Price: $12.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Everyday Ruched Knit Mini Dress

    Get an effortless everyday 'fit in this adorable ruched knit mini dress! It features trendy ruched detailing with drawstrings and can be worn as a mini or midi. Dress it up with clear mules for a date night or keep it casual with some chunky sneakers for a shopping trip.

    Fit & Features

    • Tank-like shoulder straps
    • High rounded neckline
    • Ruched detailing
    • Drawstrings at hem
    • Form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-1018

    Category Name: Casual Dresses

    Price: $13.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Off the Shoulder Long Sleeve Mini Dress

    Stun in a basic off the shoulder dress that keeps it casual and cute. The dress features an off the shoulder neckline, long ruched sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with plenty of stretch. Complete the look with clear mules.

    Fit & Features

    • Off the shoulder neckline 
    • Long ruched sleeves
    • Mini length silhouette
    • Knit fabric 
    • Form-hugging fit 
    • Plenty of stretch 

    Style Number/Barcode: 05102-0937

    Category Name: Casual Dresses

    Price: $9.97 $31.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • All Buttoned Up Off The Shoulder Midi Dress

    Get all buttoned up in this adorable off the shoulder midi dress! It features a complete button-down front with a curve-hugging, mid-length fit. Perfect for everyday, pair this dress with heeled booties to take your look into fall.

    Fit & Features

    • Off the shoulder neckline
    • Short fitted sleeves
    • Complete button-down front
    • Mid-length, form-hugging fit
    • Ribbed knit fabric

    Style Number/Barcode: 05102-0943

    Category Name: Casual Dresses

    Price: $19.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Stunning Snake Print Mesh Mini Dress

    Stun in a trendy snake print dress that makes a stylish statement! Throw this dress on with your favorite black heels for your next GNO. The dress features a sleeveless square neckline, sleek bungee straps, and a snake print. The dress is composed of mesh fabric that offers a form hugging fit with a moderate stretch. 

    Fit & Features

    • Sleeveless square neckline
    • Bungee straps
    • Snake print
    • Mini length silhouette
    • Mesh fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0936

    Category Name: Casual Dresses

    Price: $6.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Trendy Ribbed Mini Dress

    Keep it trendy in a ribbed mini dress that is perfect for nails those casual vibes! The dress features a square 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 your look with chunky sneakers. 

    Fit & Features

    • Square neckline
    • Long sleeves
    • Mini length silhouette 
    • Ribbed knit fabric 
    • Form hugging fit
    • Moderate stretch
    • Double lined

    Style Number/Barcode: 05102-0940

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Totally Chic Ruched Knit Mini Dress

     Keep it totally chic in a ruched mini dress! The dress features an off the shoulder neckline, long fitted sleeves, and a ruched drawstring center. The dress is composed of a ribbed knit fabric that hugs curves in all the right places. Complete look with sneakers for a casual look. 

    Fit & Features

    • Off the shoulder neckline
    • Long fitted sleeves
    • Ruched drawstring center
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 05102-0932

    Category Name: Casual Dresses

    Price: $14.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simple And Sleek Tie Shoulder Slip Dress

    Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.

    Fit & Features

    • Tie shoulder straps
    • Slight V neckline
    • Square back
    • Flowy mid-length fit
    • Woven fabric

     

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

    Style Number/Barcode: 05101-0895

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

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

    Keep it cute and casual in a wrap mini dress that is perfect for dinner with the squad. The dress features an off the shoulder neckline, long Dolman sleeves, a bar strap accent at the back, a cinching tie waist belt, 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 ankle booties. 

    Fit & Features

    • Off the shoulder neckline
    • Bar strap at the back 
    • Long Dolman sleeves
    • Tie waist belt with belt loops
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch 

    Style Number/Barcode: 06005-0804

    Category Name: Casual Dresses

    Price: $24.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Basic Vibes Knit Midi Dress

    Rock those basic vibes in a dress that keeps it comfortable and chic. The everyday dress features a sleeveless bodice, a v-neckline with notched detail, and a midi length silhouette. Complete your look with chunky sneakers and a chunky necklace to create a trendy streetwear look. 

    Fit & Features

    • Sleeveless bodice
    • V-neckline with notched detail 
    • Midi length silhouette
    • Knit fabric
    • Form hugging fit 
    • Moderate stretch 

     

     

    Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0924

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Basic Midi Dress

    Bring it back to basics in a ribbed dress that showcases your curves in all the right places. The dress features a scoop neckline, long sleeves, 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 ankle booties. 

    Fit & Features

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

    Style Number/Barcode: 06005-0800

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty Floral Polka Dot Mini Dress

    Create a flirty first impression in this pretty floral polka dot mini dress! It features a cowl neckline, a flowy mini length silhouette, and a fun floral print on a polka dot woven fabric. For a cute day date look, layer on a denim jacket and pair with some clear heels.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • Flowy mini length fit
    • Floral print
    • Polka dot woven fabric

     

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

    Style Number/Barcode: 05102-0914

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Floral Flair Woven Midi Dress

    You'll have that total floral flair in this stunning woven midi dress! Featuring a V neckline and a flowy mid-length silhouette, this dress would be perfect for a fall date night. Pair with some clear heels and accessorize with gold hoops to let the dress make the statement.

    Fit & Features

    • Adjustable spaghetti straps
    • V neckline
    • Back zipper closure
    • Flowy mid-length fit
    • Ditsy floral print
    • Woven fabric


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

    Style Number/Barcode: 05102-0915

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feline Fashionista Leopard Mesh Mini Dress

    Keep it fierce in a leopard dress that shows off your affinity for style! The mini dress features a leopard print, a sleeveless square neckline, and sleek spaghetti straps. Complete your night-out look with black mules.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Leopard print pattern 
    • Mini-length silhouette
    • Lined mesh fabric
    • Form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-0927

    Category Name: Casual Dresses

    Price: $9.97 $27.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keeping Knit Real Ruched Mini Dress

    Keep it real in this chic mini dress for your next outing with the squad! The dress features a crew neckline, ruched side seams with drawstrings at the hem, and a curve-hugging mini-length silhouette. Complete your look with mules.

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Ruched side seams
    • Drawstrings at the hem
    • Mini-length silhouette
    • Smooth knit fabric
    • Form-hugging fit, moderate stretch

    Style Number/Barcode: 05102-0921

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Off The Shoulder Brushed Knit Mini Dress

    Elevate your everyday style with this adorable brushed knit mini dress! It features an off the shoulder fold-over neckline with long fitted sleeves and a short, curve-hugging silhouette. Pair this dress with heeled booties for the perf winter date night with bae.

    Fit & Features

    • Off the shoulder fold-over neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Stretchy ribbed brushed knit fabric
    • Stretchy knit lining
    • Merrow edge hems

    Style Number/Barcode: 05102-0917

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Must-Have Ribbed Knit Mini Dress

    This must-have ribbed knit mini dress needs to be in your closet this season! It features a mock neckline, long fitted sleeves, a short, form-hugging fit, and a cute merrow edge trim. Pair this dress with chunky sneakers for a casual 'fit to hang with the squad.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Mini length silhouette
    • Curve-hugging fit
    • Ribbed knit fabric with plenty of stretch
    • Merrow edge trim

    Style Number/Barcode: 05102-0928

    Category Name: Casual Dresses

    Price: $12.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance