Casual Dresses

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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.

  • Stylishly Ruched Ribbed Knit Mini Dress

    This stylish ruched ribbed knit mini is the perf everyday dress you need in your closet! Featuring trendy ruched detailing and double ties at each side, this dress can be worn as a mini or a midi. Pair with some sleek booties for your new fave fall 'fit.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Ruched detailing
    • Double ties at each side
    • Ribbed knit fabric
    • Form-hugging fit

    Style Number/Barcode: 05102-0838

    Category Name: Casual Dresses

    Price: $19.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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
  • Keep It Rosey Slip Midi Dress

    Keep it rosey in this cute slip dress that keeps your look effortlessly pretty! Step out this season in a slip dress that features a pretty floral print, a high side slit and a midi length silhouette. Complete your look with clear heels and fringe earrings

    Fit & Features

    • Plunging v-neckline
    • Adjustable spaghetti straps
    • Floral print
    • High side slit
    • Midi length silhouette
    • Lightweight woven fabric
    • Relaxed fit

     

    Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

    Style Number/Barcode: 05102-0836

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Basic V Neck Knit Mini Dress

    Sometimes it's a good thing to be basic! This knit mini dress features a deep V neckline and a short, flattering, curve-hugging fit. Keep it casual with some chunky sneakers and gold hoops for a day date with bae.

    Fit & Features

    • Spaghetti straps
    • V neckline
    • Square back
    • Mini length silhouette
    • Double-lined knit fabric

    Style Number/Barcode: 05102-0880

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cozy Style Vibe Striped Knit Long Sleeve Mini Dress

    Lean into the cozy style vibes with this trendy striped ribbed knit mini dress featuring a mock neckline, long fitted sleeves, and a short bodycon silhouette to hug your curves. Pair with knee-high boots!

    Fit & Features

    • Striped ribbed knit fabric, plenty of stretch
    • Mock neckline, lettuce-edge trim
    • Long fitted sleeves, lettuce-edge trims
    • Mini-length bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5882

    Category Name: Casual Dresses

    Price: $19.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • 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
  • 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
  • Total Babe Sultry Ruched Mini Dress

    Hey babe! Get ready to werk it in this sultry ruched mini dress! Featuring a short, curve-hugging silhouette and an allover polka dot print, this little black dress is perf for a date night out. Simply add on some chic mules and you'll be gorgeous from head to toe.

    Fit & Features

    • Adjustable spaghetti straps
    • Scoop neckline
    • High waist seam under bust
    • Ruched, form-hugging fit
    • Dual drawstrings at hem
    • Mini length silhouette
    • Polka dot printed mesh fabric

    Style Number/Barcode: 05102-0636

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Viper Vixen Snake Print Mini Dress

    You'll be a total stylish vixen in this trendy snake print mini dress! It features a flattering square neckline and a curve-hugging fit. Keep it chic with some dazzling duster earrings and heels for a night out.

    Fit & Features

    • Spaghetti straps
    • Square neck and back
    • Short, form-hugging fit
    • All over snake print
    • Knit fabric

    Style Number/Barcode: 05102-0837

    Category Name: Casual Dresses

    Price: $10.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • 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
  • Such A Dream Tie Dye Ruched Mini Dress

    You'll look like such a dream in this trendy tie dye mini dress! It features ruched detailing with side ties and a form-fitting style that will hug your curves. Pair this dress with some sleek gold hoops and chunky sneakers for that perf everyday vibe.

    Fit & Features

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

    Style Number/Barcode: 05102-0867

    Category Name: Casual Dresses

    Price: $13.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • All About Knit Mock Neck Mini Dress

    You'll be totally all about this chic mock neck mini dress! Featuring long fitted sleeves and a curve-hugging fit, this dress is perfect for the fall season. Pair with gold hoop earrings and chunky sneakers for that fab everyday 'fit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Knit fabric

    Style Number/Barcode: 05102-0855

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Timelessly Chic Ribbed Knit Basic Midi Dress

    Keep it timelessly chic in a dress that wows! Perfect for a cocktail event or making the right first impression, this mini dress is a must! The dress features a crew neckline with a racer bust, a fitted form-hugging fit, and composed of a ribbed knit fabric. Complete your chic outfit with mules and duster earrings.

    Fit & Features

    • Sleeveless crew neckline
    • Racer bust
    • Ribbed knit fabric
    • Form hugging fit
    • Midi length silhouette

    Style Number/Barcode: 05102-0894

    Category Name: Casual Dresses

    Price: $9.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Every Day Knit Mini Dress

    Keep it cute in a basic mini dress that is perfect to wear any day! The dress features an off the shoulder neckline with a boat neck bust, short sleeves, and composed of a flattering knit fabric. Complete your outfit with sleek stilettos and a cute crossbody.

    Fit & Features

    • Off the shoulder neckline
    • Short sleeves
    • Boat neckline
    • Mini length silhouette
    • Knit fabric 
    • Form hugging fit, moderate stretch

    Style Number/Barcode: 05102-0892

    Category Name: Casual Dresses

    Price: $9.97 $16.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • So Fierce Ribbed Knit Mini Dress

    Keep it fab and fierce in a mini dress that keeps your look on point! The ribbed mini dress features a plunging sweetheart neckline, bust seams at the cups, adjustable spaghetti straps, and composed of a form-hugging ribbed knit fabric. Complete your look with hoop earrings and wedge heels

    Fit & Features

    • Sleeveless sweetheart neckline
    • Adjustable spaghetti straps 
    • Bust seams at the cups
    • Mini length silhouette
    • Ribbed 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: 05102-0792

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    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
  • Simply Amazing Long Bell Sleeve Mini Dress

    A simply amazing little black dress you'll adore wearing on dressy occasions! It features a square neckline, long bell sleeves with trendy ruched adjustable ties and slit accents, a flattering bodycon silhouette, and a mini-length hem. The dress is composed of a double-lined soft brushed knit fabric. Complete the look with a chic mini purse and heels.

    Fit & Features

    • Double-lined soft brushed knit fabric
    • Moderate stretch
    • Square neckline
    • Long bell sleeves, ruched adjustable ties, slit accents
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5318

    Category Name: Casual Dresses

    Price: $5.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

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

    Throw it back in a retro dress that gives us groovy feels. The dress features a sleeveless square neckline, a tie-dye print, and mini length silhouette with ruched drawstrings to customize fit or create an asymmetrical hem. Complete your outfit with trendy block heels and fringe earrings

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Tie-Dye print 
    • Mini length silhouette 
    • Ruched drawstring
    • Smooth knit fabric 

     

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

    Style Number/Barcode: 05102-0845

    Category Name: Casual Dresses

    Price: $11.97 $29.90

    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