Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and your calendar.
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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.
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Sultry Ruched Snake Print Mini Dress
You'll look so sultry and stylish in this trendy snake print mini dress. It features a V neckline, long fitted sleeves, front ruched detailing, and a short, curve-hugging fit. Pair this dress with sleek gold hoop earrings and a chic clutch for a night out.
Fit & Features
- V neckline
- Long fitted sleeves
- Front ruched detailing
- Mini length
- Form-hugging fit
- Snake print
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-1073
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Real Ruched Mini Dress
Keep it real in this dress that keeps it chic! The dress features a mock neck, long sleeves, ruched side seams, and a mini length silhouette. The dress is composed of knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sleek mules.
Fit & Features
- Mock neck
- Long sleeves
- Ruched side seams
- Mini length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0870
Category Name: Casual Dresses
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Chic Mini Dress
Style up this trendy mini dress for a casually chic look! It features tank-like shoulder straps, a scoop neckline, and a short, curve-hugging fit. Pair this ribbed knit dress with the matching jacket and chunky sneakers for the perf everyday 'fit.
Shop Matching Jacket: Casually Chic Cropped Jacket
Fit & Features
- Tank-like shoulder straps
- Scoop neckline
- Short, form-hugging fit
- Ribbed knit fabric
- Moderate stretch
Style Number/Barcode: 05102-1061
Category Name: Casual Dresses
Price: $19.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Stunning Strapless Cutout Striped Mini Dress
Take a stroll looking stunning in this striped mini dress with a sexy cutout and bodycon silhouette to flaunt your figure!
Fit & Features
- Striped print, stretchy knit fabric
- Strapless sweetheart neckline
- Button accents, cutout bodice
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2233
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Vibes Word Screen Ruched Dress
Showcase those good vibes in this trendy ruched dress! It features tank-like shoulder straps, a round neckline, side ties, and can be worn as a mini or midi dress. The knit fabric has an all-over word screen print for a cool look. Pair this dress with chunky sneakers to keep it casual or strappy heels for an elevated 'fit.
Fit & Features
- Tank-like shoulder straps
- Round neckline
- Ruched detailing
- Side ties at the hem
- Word screen print
- Knit fabric with plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1071
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Mood Ribbed Knit Maxi Dress
We're in the mood for basics! Slay in this dress that keeps it effortlessly chic. The dress features a trendy turtle neck, long sleeves, and a maxi length silhouette with a high center back slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with sneakers to nail those low-key vibes.
Fit & Features
- Turtle neck
- Long sleeves
- Maxi length silhouette
- High center back slit
- Ribbed knit fabric
- Plenty of stretch
- Form-hugging fit
Style Number/Barcode: 05102-1117
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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Cozy Knit Long Sleeve Tunic
You'll be so cozy and chic in this adorable knit tunic! It features a ribbed crew neckline, long sleeves with ribbed hems, a low V back with a strap detail, side slits, and a relaxed and comfortable fit. Pair this tunic with leggings and ankle booties or wear it as a dress with thigh-high boots.
Fit & Features
- Ribbed crew neckline
- Long sleeves with ribbed hems
- Low V back with strap detail
- Side slits
- Relaxed fit
- Knit fabric with minimal stretch
Style Number/Barcode: 06005-0716
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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Effortlessly Chic Sleeveless Mini Dress
You'll look so effortlessly chic in this simple yet stylish mini dress! It features a sleeveless bodice, a high neckline, and a mini length, curve-hugging silhouette. The knit fabric is lined and offers plenty of stretch for comfortable wear. Pair this dress with a denim jacket for a casual look or a blazer for an elevated vibe.
Fit & Features
- High neckline
- Short, form-hugging fit
- Lined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0994
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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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
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Slay In Basics Ribbed Knit Mini Dress
Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. 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
- Mock neck
- Long sleeves
- Rounded mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0852
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keepin' Knit Cute Ruched Mini Dress
Keep your 'fit cute and stylish in this knit mini dress! It features a crew neckline, long fitted sleeves, a high waist seam, front ruched detailing with dual adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Pair this dress with chunky sneaks for a casual feel, or dress it up with heels and a layered necklace.
Fit & Features
- Crew neckline
- Long fitted sleeves
- High waist seam
- Front ruched detailing
- Dual adjustable drawstrings at the hem
- Short, form-hugging fit
- Brushed knit fabric with plenty of stretch
Style Number/Barcode: 05102-1047
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep Knit Cozy Mini Sweater Dress
Keep your look cozy and chic in this mini sweater knit dress! It features a trendy mock neckline, long fitted sleeves, and a short, curve-hugging silhouette. Pair this dress with thigh-high boots for an adorable date night 'fit.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Front seam detailing
- Short, form-hugging fit
- Sweater knit fabric with moderate stretch
Style Number/Barcode: 06005-0717
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Casual Hoodie Mini Dress
Keep it casual in a mini dress that is part cozy and part glam. The hoodie mini dress features a corset bodice with piping detail, long sleeves, a hoodie, and a mini length silhouette. The mini dress is composed of a knit fabric that offers a form hugging fit. Complete look with chunky sneakers.
Fit & Features
- Corset-like bodice with piping seams
- Hoodie
- Long sleeves with ribbed cuff
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 06002-0670
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Play On Sleeveless Plaid Mini Dress
Keep it playful and poised in a dress that is totally on-trend, babe! The dress features a sleeveless scoop neckline, a plaid print, and a mini length silhouette. The dress is composed of a brushed knit fabric. Complete look with ankle booties.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Plaid print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1067
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Knit Cute and Casual Ribbed Midi Dress
Keep it cute and casual in a knit dress that is perfect for a quick coffee run or a casual date with bae. The dress features a scoop neckline, long sleeves, a midi length silhouette, and composed of a ribbed brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers.
Fit & Features
- Scoop neckline
- Long sleeves
- Midi length silhouette
- Ribbed
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1042
Category Name: Casual Dresses
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Flair Striped Knit Off-The-Shoulder Mini Dress
Showcase a cozy flair in this mini dress made with striped ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette for an adorable vibe.
Fit & Features
- Striped ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5883
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Basic Ribbed Knit Mini Dress
Rock a basic mini dress for that next coffee date with bae or layer up for a casual shopping spree. The dress features a notched V-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 look with ankle booties.
Fit & Features
- Notched V-neckline
- Long sleeves
- Mini length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1060
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Crush Cozy Mini Dress
You'll absolutely love this cozy crush-worthy mini dress! It features an off the shoulder fold-over neckline, long blouson sleeves with tapered hems, and a mini length, curve-hugging silhouette. The lightweight knit fabric has a cashmere-like feel and offers plenty of stretch. Pair this dress with thigh-high boots for the perf holiday look.
Fit & Features
- Off the shoulder fold-over neckline
- Long blouson sleeves
- Short, form-hugging fit
- Soft knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0970
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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
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Stylish Babe Scoop Neck Mini Dress
You'll be a total stylish babe in this chic mini dress! It features a wide scoop neckline, long fitted sleeves, and a curve-hugging, mini length silhouette. The dress is composed of a brushed knit fabric with plenty of stretch for comfortable wear. Pair this dress with thigh-high boots to elevate it to a night out look!
Fit & Features
- Wide scoop neckline
- Long fitted sleeves
- Short, form-hugging fit
- Brushed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0986
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Knit Girl Turtleneck Mini Dress
You'll be a major it girl in this adorable ribbed knit mini dress! It features a cozy turtleneck, long fitted sleeves, and a mini length, curve-hugging silhouette. This dress is perf for a holiday party, styled with thigh-high boots for a chic look.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Short, form-hugging fit
- Ribbed knit fabric
- Moderate stretch
Style Number/Barcode: 05102-0589
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance