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.

  • Falling For Chic Mock Neck Dress

    You'll be falling for the chicness of this mock neck dress! It features long sleeves, a midi-length hem, and a bodycon silhouette. The rib-knit fabric offers a moderate stretch. Complete your look with a boater hat and booties.

    Fit & Features

    • Long sleeves
    • Mock neckline
    • Midi length hem
    • Bodycon silhouette
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4302

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Keeping Up With Knit Colorblock Mini Dress

    Keep up this season in a fab mini dress that is perf to layer on the style! The dress features a crew neckline, long sleeves, a colorblock pattern, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties!

    Fit & Features

    • Crew neckline
    • Long sleeves
    • Colorblock pattern with exposed seams
    • Mini-length silhouette
    • Knit fabric
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4300

    Category Name: Casual Dresses

    Price: $9.97 $33.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Back To Basics Turtleneck Mini Dress

    Your head-to-toe look needs this turtleneck dress as a base for creating fab looks! It features fitted long sleeves and a short-length hem. This dress is composed of crepe-lined fabric with a moderate stretch. Style with a duster coat. 

    Fit & Features

    • Fitted long sleeves
    • Turtleneck design
    • Bodycon silhouette
    • Short-length hem
    • Crepe-lined knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4299

    Category Name: Casual Dresses

    Price: $9.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Casual-Chic Moment Mini Dress

    Have a stylish casual-chic moment in this ribbed knit mini dress. It features a crew neckline, long fitted sleeves, a trendy wrap tie-front design, and a short, form-hugging silhouette. Complete the look with heeled booties.

    Fit & Features

    • Crew neckline
    • Long fitted sleeves
    • Wrap tie-front design
    • Mini-length, form-fitting silhouette
    • Ribbed knit fabric, knit lining, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4298

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Daring Diva Open Back Midi Dress

    Dare to go bold with a midi dress that wows! The dress features a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and a midi-length silhouette. Complete look with stilettos and door knocker earrings. 

    Fit & Features

    • Sleeveless scoop neckline 
    • Adjustable spaghetti straps, cross at back
    • Open back 
    • Midi length silhouette
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1210

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Endless Summer Halter Cutout Dress

    Embrace the summer vibes in this chic curve-hugging dress! It features a sleeveless halter neckline, an open back, a center knot detail with dual waist cutouts, and an ankle-length, form-fitting silhouette. Style this dress with sleek hoop earrings.

    Fit & Features

    • Sleeveless halter neckline
    • Open back
    • Center knot detail
    • Dual waist cutouts
    • Long, form-hugging fit
    • Ribbed sweater knit fabric
    • Runs true to size

    Style Number/Barcode: 06005-1216

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cut Above The Rest Ribbed Knit Mini Dress

    Step into a league of your own with a ribbed knit mini dress! The dress features a one-shoulder neckline, an asymmetrical midriff cutout, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging with a moderate stretch. Complete look with mules. 

    Fit & Features

    • One-shoulder neckline
    • Asymmetrical midriff cutout 
    • Mini length silhouette
    • Ribbed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 06005-1212

    Category Name: Casual Dresses

    Price: $6.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Be Mine Button-Down Ribbed Midi Dress

    One look at this midi dress and you'll want it to be yours! It features short sleeves, a scoop neck, button-down front closures, a sultry front slit, and a bodycon silhouette. Composed of rib-knit fabric with a moderate stretch. Finish the look in chic hoop earrings.

    Fit & Features

    • Short sleeves, scoop neck
    • Button-down front closures
    • Front slit, midi hem
    • Bodycon silhouette
    • Rib-knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4292

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless Vibes Babydoll Dress

    Effortless and chic, this babydoll dress is perf for casual days where you still want to dress up. It features a V-neckline, three-quarter length sleeves, and a short, flowy silhouette with a tiered design. Style this dress with cute mules.

    Fit & Features

    • V-neckline
    • Three-quarter length sleeves, cinched hems
    • Mini-length, flowy babydoll fit
    • Tiered design
    • Woven crepe fabric, textured pattern
    • Runs true to size

    Style Number/Barcode: 05102-4294

    Category Name: Casual Dresses

    Price: $9.97 $30.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Effortless And Pretty A-Line Mini Dress

    You'll look so effortlessly pretty in this adorable mini dress that is perf for a weekend brunch. It features a square neckline, a low square back design, short puff sleeves, a flattering high waist, and a short tiered skirt with an A-line silhouette. Style this dress with hoop earrings and cute wedges.

    Fit & Features

    • Square neckline
    • Low square back
    • Short puff sleeves, cinched hems
    • High waist
    • Mini-length A-line silhouette, tiered design
    • Cotton fabric
    • Runs true to size

    Style Number/Barcode: 05102-4296

    Category Name: Casual Dresses

    Price: $9.97 $48.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Ruched Babe Mock Neck Bodycon Dress

    Flaunt your babe status in this bodycon dress! It features long sleeves, a mock neckline, a ruched front, and a short-length hem. The dress is composed of a soft knit fabric with a moderate stretch

    Fit & Features

    • Long sleeves
    • Mock neckline
    • Ruched front
    • Short-length hem, bodycon style
    • Soft knit fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05102-4290

    Category Name: Casual Dresses

    Price: $19.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Major Moment High Slit Knit Midi Dress

    Create a major style moment with a midi dress that wows! The dress features a square neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties and a cabby hat.

    Fit & Features

    • Square neckline
    • Long fitted sleeves
    • High side slit
    • Midi-length silhouette
    • Knit fabric 
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4287

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Simply Sultry And Stunning Mini Dress

    You'll look simply sultry and stunning in this lightweight knit mini dress! It features a strappy cross-front design with a V-neckline, long fitted sleeves, an open back with a strappy cross-back design, and a short, curve-hugging fit. Style this dress with clear mules.

    Fit & Features

    • Front and back cross-strap designs
    • V-neckline
    • Open back
    • Long fitted sleeves
    • Mini-length, form-fitting silhouette
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4289

    Category Name: Casual Dresses

    Price: $9.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Major Stunner Brushed Knit Mini Dress

    Stun like the major babe you are with a chic mini dress! The dress features a collared neckline, short sleeves, a zipper front closure, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a clear clutch.

    Fit & Features

    • Collared neckline
    • Zipper front
    • Short sleeves
    • Mini length silhouette 
    • Double-lined brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4286

    Category Name: Casual Dresses

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Weekend Vacay Satin Ruched Tie-Back Dress

    Planning a weekend vacay? Don't forget to pack this adorable satin dress! It features spaghetti straps and a ruched bust, a mini-length hem, and an open back with self-tie detail. Complete the look chic mules.

    Fit & Features

    • Sleeveless, spaghetti straps
    • Ruched bust
    • Mini-length hem
    • Open back with self-tie
    • Satin fabric, moderate stretch
    • Fits true to size

    Style Number/Barcode: 05101-1276

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • A Casual Slay Ruched Midi Dress

    You'll casually slay in this basic chic midi dress with elevated details. It features a mock neckline, long fitted sleeves, a curve-hugging silhouette, and a front slit with ruching. Style this dress with trendy clear mules.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Form-fitting silhouette
    • Front slit, ruching
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4284

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Flirty And Flowy Woven Mini Dress

    Flirty and flowy, this adorable woven mini dress is perfect for day dates! It features a V-neckline, long blouson sleeves, a high waist seam, and an A-line silhouette with tiered ruffle detailing. The lightweight woven fabric includes a knit lining. Complete the look with a denim jacket and mules.

    Fit & Features

    • V-neckline
    • Long blouson sleeves, tapered hems
    • Back zipper and hook and eye closure
    • High waist seam
    • A-line silhouette, tiered ruffle detailing
    • Woven fabric, knit lining, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4280

    Category Name: Casual Dresses

    Price: $19.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Chic Basic Mock Neck Mini Dress

    This mini dress is the perfect day-to-night style! It features long sleeves, a mock neckline, and a bodycon silhouette designed to accentuate your curves. Complete the look with a necklace.

    Fit & Features

    • Long fitted sleeves
    • Mock neckline
    • Bodycon silhouette
    • Mini-length hem 
    • Runs true to size

    Style Number/Barcode: 05102-4281

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet And Sassy Chiffon Mini Dress

    Sweet and sassy will be your go-to style in this adorable chiffon mini dress. It features a sweetheart neckline, a tie-front detail at the bust, long sheer bishop sleeves, a stretchy smocked back design, a short, form-hugging silhouette, and an all-over leopard print pattern. Complete the outfit with clear mules and a trendy shoulder bag.

    Fit & Features

    • Sweetheart neckline
    • Tie-front detail at the bust
    • Long sheer bishop sleeves, elastic cinched hems
    • Stretchy smocked back design
    • High waist seam, mini-length, form-fitting silhouette
    • Sheer chiffon fabric, knit lining, leopard print
    • Runs true to size

    Style Number/Barcode: 05101-1267

    Category Name: Casual Dresses

    Price: $19.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Oh-So-Fab Tie-Dye Maxi Dress

    Keep your look trendy and fab in this curve-hugging tie-dye maxi dress. It features a sleeveless asymmetrical one-shoulder neckline, a single spaghetti strap, a flattering high waist seam, and a form-fitting maxi-length silhouette with a sultry thigh-high side slit. Complete the outfit with clear heels.

    Fit & Features

    • Sleeveless asymmetrical one-shoulder neckline
    • Single spaghetti strap
    • High waist seam
    • Maxi-length silhouette, form-hugging fit
    • High side slit, ruched detailing
    • Knit fabric, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4277

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Cross Out The Drama Bodycon Dress

    Cut the drama from your life in a dress that features a halter neck, cross-straps at the bodice, a sexy cutout at the midriff, a bold open back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Halter neck
    • Cross-straps at bodice
    • Cutout at the midriff
    • Open back 
    • Mini-length silhouette
    • Cotton knit fabric, form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4392

    Category Name: Casual Dresses

    Price: $9.97 $25.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Daring Chic Cutout Mini Dress
    Dare to go bold with a dress that is anything but basic! The dress features a collared neckline, a multi-button down front, long sleeves, dual waist cutouts, 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 clear heels and a crossbody. 

     

    Fit & Features

    • Collared neckline
    • Multi-button down front
    • Long sleeves
    • Dual waist cutouts
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4276

    Category Name: Casual Dresses

    Price: $5.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • All The Right Moves Ruched Mini Dress

    Make all the right moves with a mini dress that showcases your curves! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Ruched body
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4275

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sultry Strappy Waist Sleeveless Midi Dress

    This ribbed knit midi dress is the perf option for a casual yet still sultry look! It features a sleeveless crew neckline, tank shoulder straps, a front waist cutout with a strappy design, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with strappy heels.

    Fit & Features

    • Sleeveless crew neckline
    • Tank shoulder straps
    • Front waist cutout, strappy design
    • Mid-length, form-hugging fit
    • Side slit
    • Lined ribbed knit fabric, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-4272

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale