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.

  • Classic Chic Scoop Neck Knit Mini Dress

    Fall in love with the classic chic look of this adorable basic knit mini dress! It features bungee spaghetti straps and a short, flattering, curve-hugging fit. This dress can easily be dressed up with heels for date night or kept more casual with a bucket hat and chunky sneakers for a shopping day.

    Fit & Features

    • Bungee spaghetti straps
    • Scoop neckline
    • Mini-length silhouette
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-0897

    Category Name: Casual Dresses

    Price: $9.97 $18.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • 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
  • Brighter Vibes Lace-Up Chiffon Maxi Dress

    Bring on brighter vibes in this maxi dress that brings a burst of color this season. The maxi dress features a plunging v-neckline, sexy waist cutout to show off a hint of skin, a lace-up back, and a high side slit. Complete your look with fab cork wedges and sunnies for those ultimate summer vibes. 

    Fit & Features

    • Sleeveless v-neckline with spaghetti straps
    • Waist cutouts
    • Lace-up back 
    • High side slit
    • Maxi length silhouette
    • Chiffon fabric 


    Model is 5'8" with a 34" bust, 24" waist and 35" hips. She is wearing a size small.

    Style Number/Barcode: 05101-0505

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Lovin' The Basics Cotton Midi Dress

    You'll be lovin' everything about this basic cotton midi dress! Featuring a crew neckline and a mid-length, curve-hugging fit, this dress will flatter your figure. Pair with some gold hoops and chunky sneakers for a laid back, casual vibe you can wear to hang out with your squad.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Mid-length silhouette
    • Cotton fabric

    Style Number/Barcode: 05102-0926

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    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
  • Late Night Fantasy Dress

    Live your wildest dreams in this dress! Bring the wow factor to your date-night outfit in this flirty skater dress. The dress features a flattering v-neckline, spaghetti straps that offer support, sheer lace back detail with a lower back keyhole to show off a hint of skin and a flowy skater silhouette with double-tiered hem. The dress is composed of a form-hugging ponte knit fabric that offers a moderate stretch. Complete your impressive look with rhinestone duster earrings and sleek stiletto heels

    Fits & Features

    • V neckline
    • Spaghetti straps
    • Sheer lace back with zipper
    • Exposed lower back
    • Wide waistband 
    • Flowy skirt with a double-tiered hem 
    • Ponte knit composition, moderate stretch

     

    Black Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.

    Ivory Dress: Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.

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

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

    Mauve Dress: Model is 5'3" with a 32" bust, 22.5" waist and 34" hips. She is wearing a size small.

    *Also available in Plus

    Style Number/Barcode: 05101-7048

    Category Name: Casual Dresses

    Price: $6.97 $47.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Keep It Cool And Casual Tunic

    Keep your look cool & casual in a tunic. This tunic looks great worn alone or dressed up with layers for a casually cute date night look. The tunic features a crew neckline, short sleeves, and a short curved hem to flatter curves. The tunic is composed of a cotton-blend fabric that offers a form hugging fit with a moderate stretch. Pair with some white sneakers, a denim jacket, and a baseball cap for that sporty chic vibe.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Short curved hem
    • Form hugging fit
    • Cotton blend fabric
    • Moderate stretch
    • Runs true to size

    Style Number/Barcode: 06002-0439

    Category Name: Casual Dresses

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Short And Sweet V-Neck Bodycon Mini Dress

    Keep your style short and sweet in this sassy bodycon mini dress perf for casual weekend plans or dressing up with a cute jacket and heels!

    Fit & Features

    • Stretchy knit fabric
    • Short sleeves
    • V-neckline
    • Bodycon silhouette
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5957

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • That's My Stripe Crepe Triangle Waist Cut Out Mini Dress

    This striped crepe waist cut out mini dress will be just your type! Featuring a sultry cutout, a streamlined silhouette, and trendy stripes, this dress checks all the boxes. Opt for some booties and statement earrings to go with this look for a night out.

    Fits & Features

    • Spaghetti straps
    • V Neckline and vertical dart seams 
    • Square back with no zipper
    • Triangular waist cut out
    • Mini length silhouette 
    • Crepe fabric 
    • Form-hugging fit with moderate stretch

    Style Number/Barcode: 05103-0292

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Ribbed Knit Crew Neck Maxi Dress

    This simple yet stunning ribbed knit maxi dress is a must for your fab fall look. Featuring a high crew neckline and a flattering curve-hugging silhouette, this dress can easily be dressed up with some strappy heels or down with a pair of chunky sneakers. Wear on a casual date night with bae.

    Fit & Features

    • High crew neckline
    • Tank-like shoulder straps
    • Form-hugging fit
    • Side slit
    • Maxi length
    • 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: 05102-0870

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Trendy Tie Dye Midi Dress

    This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.

    Fit & Features

    • High rounded neckline
    • Mid-length silhouette
    • Form-hugging fit
    • Tie dye print
    • Knit fabric

     

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

    Style Number/Barcode: 05102-0866

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    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
  • Flirty Silhouette Lace Trim Plaid Mini Dress

    Flirty and adorable, this plaid woven mini dress features a sleeveless sweetheart neckline with a dainty eyelet lace and ribbon trim and front bow detail, spaghetti straps, and a short form-hugging silhouette to highlight your curves. Style with hoop earrings and sleek mules.

    Fit & Features

    • Plaid woven-blend fabric with moderate stretch, knit lining at the bust
    • Sweetheart neckline with lace and ribbon trim, front bow detail
    • Ruched bust, underbust seam
    • Spaghetti straps
    • Mini-length form-hugging fit
    • Runs true to size

    Style Number/Barcode: 05102-5934

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Fall For Floral Woven Midi Dress

    Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.

    Fit & Features

    • Adjustable spaghetti straps
    • Cowl neckline
    • 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: 05102-0882

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    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
  • Walk in the Park Floral Mini Dress

    Take a stroll in style wearing this sweet floral dress! Pair it with sandals and a straw bag.

    Fit & Features

    • Ribbed Fabric
    • Off the Shoulder Puff Sleeves
    • Tie Front Detail
    • Mini Length

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

    Style Number/Barcode: 05101-0447

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Simply Perfect Knit Mini Dress

    Get a simply perfect 'fit with this basic knit mini dress! With its fitted long sleeves and curve-hugging silhouette, this stretchy knit dress is oh-so-flattering. A definite for your next date night, keep it casual with a pair of chunky sneakers or glam it up with some bold block heels.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Short, form-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch

    Style Number/Barcode: 06002-0519

    Category Name: Casual Dresses

    Price: $6.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Strapless Tube Tie Dye Midi Dress

    Make a splash in a tie-dye dress that brings some serious summer vibes! Step out for that backyard bbq with the squad in this colorful midi dress. The dress features a strapless tube neckline, a tie-dye print, and a curve-hugging midi-length silhouette. Complete your summer outfit with clear heels

    Fit & Features

    • Sleeveless tube neckline
    • Tie-dye pattern
    • Midi length silhouette
    • Form hugging knit fabric
    • Moderate stretch 

     

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

    Style Number/Barcode: 05102-0831

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • The Every Day Tube Midi Dress

    Step out in this staple dress to wear any day for any occasion! This midi dress is perfect for dressing up with heels to create a night out outfit or dressing down with sneakers for a casual coffee date. The dress features a sleek tube neckline and a midi length silhouette with a mini side slit. 

    Fit & Features

    • Sleeveless straight tube neckline
    • Midi length silhouette
    • Mini side slit
    • Knit fabric
    • 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: 05102-0827

    Category Name: Casual Dresses

    Price: $9.97 $19.90

    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
  • Season of Stripes Cutout Gauze Mini Dress

    Keep it sassy in a striped dress this season to keep on-trend! Make a stunning impression for that upcoming date in a dress that features a plunging V-neckline, sexy bar waist cutouts, and a trendy striped design. Complete look with wedges and fringe earrings to channel bohemian vibes. 

    Fit & Features 

    • Sleeveless V-neckline
    • Smocked waist
    • Bar waist cutouts
    • Striped pattern
    • Mini length silhouette
    • Gauze-linen fabric
    • Form hugging fit, minimal stretch 

     

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

    Style Number/Barcode: 05102-0414

    Category Name: Casual Dresses

    Price: $9.97 $40.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Open Back High Slit Floral Dress

    Show off your affinity for florals in a dress that creates major head-turning appeal! Step out for brunch with your squad in this pretty in pink dress! The dress features a high round neckline, cap sleeves, a lower back keyhole, and a high side slit. Complete look with clear heels and mini purse.

    Fit & Features

    • High round neckline
    • Cap sleeves
    • Lower back keyhole
    • Floral print 
    • High side slit
    • Midi-length silhouette
    • Lightweight woven fabric

     

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

    Style Number/Barcode: 05102-0834

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Feelin' Fresh In Floral Ruffle Hem Mini Dress

    Get a fresh look in this gorg floral ruffle hem mini dress! It features woven tie shoulder straps and cute ruffle detail at the hem for a fun and flirty vibe. A must-have for your next backyard bbq, style it up with clear slide on mules and sleek gold hoop earrings.

    Fit & Features

    • Tie shoulder straps
    • Slight sweetheart neckline
    • Partially smocked back with a hidden zipper closure
    • Short ruffle hem
    • Floral print
    • Woven fabric

     

    Model is 5'9" with a 34" bust,  24" waist and 35.5" hips. She is wearing a size small. 

    Style Number/Barcode: 05102-0833

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance