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.

  • Breaking The Rules Plaid Mini Dress

    Break the rules with a mini dress that doesn't play it safe! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, 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 thigh-high boots

    Fit & Features

    • Plaid print
    • Sleeveless square neckline
    • Spaghetti straps
    • Mini length silhouette
    • Brushed knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4168

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sweet Beauty A-Line Midi Dress

    Bring a sweet style to your everyday look with this adorable flowy midi dress. It features a square neckline, half-length puff sleeves, a partially smocked back, a high waist, and a mid-length, A-line silhouette with a tiered hem. Complete the outfit with sleek hoop earrings and cute mules.

    Fit & Features

    • Square neckline
    • Half-length puff sleeves, elastic cinched hems
    • Partially smocked back
    • High waist
    • Mid-length, A-line flowy silhouette, tiered hem
    • Cotton fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 05102-4243

    Category Name: Casual Dresses

    Price: $9.97 $54.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Cutout Crush Hour Midi Dress

    Warning: This midi dress is sure to cause double takes. From the front-tie detail to the high leg slit, it’s giving effortless bombshell, perfect for pool parties or a cute brunch!

    Fit & Features

    • Sweater knit stretchy fabric
    • V-neckline with tie bust design
    • Adjustable spaghetti straps
    • Underbust cutout accent
    • Front slit
    • Bodycon fit, midi-length hem
    • Runs true to size

    Style Number/Barcode: 06005-000014

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make A Seam Ribbed Knit Mini Dress

    Create a stylish scene with a dress that brings major exposure! The dress features a square neckline, long sleeves, exposed vertical seams that create an hourglass effect, 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 and hoops. 

    Fit & Features

    • Square neckline
    • Long sleeves
    • Exposed vertical seams
    • Mini length silhouette
    • Ribbed knit-lined fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4214

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • On That Retro Vibe Colorblock Mini Dress

    Channel those retro vibes with this fab mini dress! The dress features a colorblock pattern, a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, dual ruched drawstrings at the hem, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.

    Fit & Features

    • Colorblock pattern
    • Crew neckline
    • Long sleeves
    • Cutout at midriff, criss-cross straps
    • Dual ruched drawstrings
    • Mini length silhouette
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4192

    Category Name: Casual Dresses

    Price: $9.97 $36.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Raising The Bar Plaid Mini Dress

    Raise the bar with a mini dress that is part classy, part casual! The dress features a plaid print, a sleeveless square neckline, and a mini-length silhouette. The dress is composed of a lined knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a denim jacket

    Fit & Features

    • Plaid print
    • Sleeveless square neckline 
    • Mini length silhouette
    • Lined knit fabric 
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4256

    Category Name: Casual Dresses

    Price: $19.97 $28.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Pull In Closer Tie Dye Mini Dress

    Pull in closer with a trendy mini dress! The dress features a tie-dye print, a crew neckline, long sleeves, ruched drawstrings, 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

    • Tie-dye print
    • Crew neckline
    • Long sleeves
    • Ruched drawstrings
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4084

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Make It Chic Ribbed Knit Mini Dress

    Make a chic impression with a mini dress that gives off those effortlessly chic vibes! The dress features a sleeveless collared neckline, a button-down front, contrasting hued trim, 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 mules.

    Fit & Features

    • Sleeveless collared neckline
    • Button-down front
    • Contrasting hued trim
    • Mini length silhouette
    • Ribbed knit fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-0990

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Style Icon Denim Mini Dress

    Stun like the style icon you are with a mini dress that stuns! The dress features a sleeveless sweetheart neckline, lightly padded cups, adjustable spaghetti straps, corset-like seams at the bodice, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules

    Fit & Features

    • Sleeveless sweetheart neckline
    • Lightly padded cups
    • Adjustable spaghetti straps 
    • Corset-like seams at bodice
    • Mini length silhouette
    • Denim fabric 
    • Form hugging fit, moderate stretch, runs true to size 

    Style Number/Barcode: 05102-4085

    Category Name: Casual Dresses

    Price: $9.97 $42.90

    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
  • The Classic Plaid Mini Dress

    Keep it classy with a plaid mini dress that channels those preppy vibes! The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a lined brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with booties.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti strap
    • Plaid print
    • Mini length silhouette
    • Lined brushed knit fabric
    • Form hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4232

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casually Fab Tie-Dye Mini Dress

    Get a casually fab look in this on-trend tie-dye mini dress. It features a crew neckline, short sleeves, ruched detailing down the sides with ties at the hem, and a short, curve-hugging silhouette. Style this dress with a denim jacket and sneakers.

    Fit & Features

    • Crew neckline
    • Short sleeves
    • Ruching down the sides
    • Ties at the hem
    • Mini-length, form-hugging fit
    • Ribbed knit fabric, plenty of stretch, tie-dye print
    • Runs true to size

    Style Number/Barcode: 05102-4233

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    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
  • First In Class Plaid Mini Dress

    Keep it classy with a plaid dress that is perf for making a stylish first impression. The dress features a sleeveless square neckline, spaghetti straps, a plaid print, 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 heels

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Plaid print
    • Mini length silhouette
    • Brushed knit fabric
    • Form hugging fit, moderate stretch 
    • Runs true to size

    Style Number/Barcode: 05102-4169

    Category Name: Casual Dresses

    Price: $19.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Extra Extra Newspaper Print Mini Dress
    You'll be the talk of the town babe in this eye-catching mini dress! It's designed with a unique newspaper print, ruched tie sides, and thin spaghetti straps. Wear it with hoops and lace-up heels to be tomorrow's front page news!

    Fit & Features
    • Bodycon fit with moderate stretch
    • Thin spaghetti straps
    • V-neckline
    • Ruched sides with ties
    • Brushed knit fabric, newspaper print
    • Runs true to size 

    Style Number/Barcode: 05102-4203

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Own That Ruched Tie Bodycon Dress
    It's time to own the night, and this bodycon dress is the way to do it! It features a stunning ruched front detail, short sleeves, and a round neckline. Slip it on with lace-up heels for total babe vibes. 

    Fit & Features
    • Short sleeves
    • Round neckline
    • Ruched front detail
    • Bodycon fit
    • Fits true to size

    Style Number/Barcode: 05102-4167

    Category Name: Casual Dresses

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Abstract Beauty Mesh Midi Dress

    Stun like the one-of-a-kind beauty you are with a midi dress that slays! The dress features a sleeveless square neckline, bungee spaghetti straps, an abstract-watercolor print, and a midi-length silhouette. The dress is composed of a lined mesh fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear heels.

    Fit & Features

    • Sleeveless square neckline, elastic band
    • Bungee spaghetti straps
    • Abstract watercolor print
    • Midi-length silhouette
    • Lined mesh fabric, ruched detailing
    • Form-hugging fit, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4229

    Category Name: Casual Dresses

    Price: $19.97 $35.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Style In Stride V-Neck Collar Denim Mini Dress

    Your best bet is this collar denim mini dress for a unique look at concerts or festivals! Set the trend in this sleeveless bodycon dress perf for styling with western boots.

    Fit & Features

    • Vintage-inspired denim fabric, minimal stretch
    • Collar V-neckline
    • Zip-up front closure
    • Faux front pockets
    • Bodycon fit
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5914

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Preppy Trendsetter Plaid Mini Dress

    Keep your everyday look on-trend in this preppy plaid mini dress! It features a collared V-neckline, short sleeves, a short, form-hugging silhouette, and is composed of a knit fabric with a moderate stretch. Style this dress with a denim jacket and sneakers for the perf cute and casual outfit.

    Fit & Features

    • Collared V-neckline
    • Short sleeves
    • Mini-length, form-hugging fit
    • Plaid print
    • Knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 05102-4244

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • Retro Mood Tie Dye Midi Dress

    Channel a retro mood with a midi dress that is totally fab! The dress features a tie-dye print, a crew neckline, short sleeves, and a high side slit with a twist knot accent. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a denim jacket

    Fit & Features

    • Crew neckline
    • Short sleeves
    • High side slit, twist knot accent
    • Tie-dye pattern
    • Midi length silhouette
    • Cotton kbit fabric
    • Form-hugging fit, moderate stretch, runs true to size

    Style Number/Barcode: 05102-4271

    Category Name: Casual Dresses

    Price: $9.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • 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
  • So Chic Plaid Mini Dress

    Oh-so-chic, this plaid mini dress is a staple you can take into the fall season! It features a trendy square neckline, spaghetti straps, and a short, curve-hugging silhouette. Style this knit dress with clear heels and a faux leather jacket.

    Fit & Features

    • Sleeveless square neckline
    • Spaghetti straps
    • Mini-length, form-hugging fit
    • Plaid print
    • Knit fabric
    • Runs true to size

    Style Number/Barcode: 05102-1105

    Category Name: Casual Dresses

    Price: $9.97 $26.90

    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