Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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Rocker Babe Slashed Mini Dress
Rock on babe in a tee that shows off your edgy side! The mini dress features a crew neckline, short sleeves, a bold rock-inspired graphic, a slashed design at the 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 combat boots and a swag chain belt.
Fit & Features
- Crew neckline
- Short sleeves
- Rock-inspired graphic
- Slashed design at back
- Mini length silhouette
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1027
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Girl Next Door Slip Dress
Show off your trendy style in this adorable cow print slip dress! It features a sleeveless V-neckline, bungee spaghetti straps, a stylish small front slit, and a short fitted silhouette. Complete the look with ankle booties.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Short front slit
- Mini-length fitted silhouette
- Brushed knit fabric, moderate stretch
- Cow print
- Runs true to size
Style Number/Barcode: 05102-4325
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sporty Babe Hooded Mini Dress
Achieve that trendy sporty babe look with this casual ribbed knit mini dress. It features a hoodie, a high neckline with front drawstrings, long sleeves, ruched side detailing, and a short, curve-hugging silhouette. Style this dress with cute sneakers.
Fit & Features
- Hoodie
- High neckline, front adjustable drawstrings
- Long fitted sleeves
- Ruched sides, adjustable drawstrings
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4324
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knott Love Halter Cutout Midi Dress
You'll fall for this halter midi dress with just one look! Featuring a sleeveless, halter neck with tie-back closure, a trendy knot cutout bodice that shapes the bodycon silhouette. Complete the look in classy nubuck heels.
Fit & Features
- Sleeveless, halter neck, tie-back closure
- Knot cutout bodice
- Bodycon silhouette
- Midi-length hem
- Soft and stretchy knit fabric
- Fits true to size
Style Number/Barcode: 05102-4322
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Street Rider Graphic Lace-Up Tee
Show off your need for speed with a graphic tee that gives your look an edgy feel. The tee features a crew neckline, short sleeves, a graphic that reads: " The Street Riders", an image of a skull with a helmet, and a lace-up front. The tee is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots.
Fit & Features
- Crew neckline
- Short sleeves
- Graphic: "The Street Riders"
- Image of a skull with helmet
- Lace-up front
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1024
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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On Top Of The Trends Cutout Mini Dress
Stay on top of the latest trends this fall with this casual yet chic mini dress! It features a sweetheart neckline with a center knot accent at the bust, dual asymmetric front cutouts at the waist, long fitted sleeves, and a short, form-hugging silhouette. The ribbed knit fabric has a moderate stretch for comfortable wear. Style with knee-high boots for a fall festival.
Fit & Features
- Sweetheart neckline, center knot detail at the bust
- Dual asymmetric front waist cutouts
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4320
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crazy About Ruche Collared Mini Dress
Keep on trend with a mini dress that shows off your love for ruching! The dress features a collared neckline, a multi-button down front, long sleeves, a ruched body, and a mini-length silhouette. The dress is composed of a slinky knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Collared neckline
- Long sleeves
- Multi-button down front
- Ruched body
- Mini length silhouette
- Slinky knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-1314
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 Trendy Ribbed Midi Dress
Keep it trendy with a midi dress that can be dressed up for your night date night with bae. The dress features a crew neckline, long sleeves, a ruched drawstring, a high side slit, 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 and a plaid scarf.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched drawstring
- High side slit
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4311
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plaid Perfect Sleeveless Mini Dress
Plaid will forever be a timeless and perfect print! This mini dress features a sleeveless, square neckline with spaghetti straps and a bodycon fit on a short-length hem. Composed of a soft knit fabric with a moderate stretch. Style with a cute cardigan for a casual day out.
Fit & Features
- Square neckline
- Sleeveless, spaghetti straps
- Plaid pattern
- Bodycon fit, mini hem
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4310
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Endless Sun Crepe Knit Midi Dress
Bare your shoulders in this floral midi dress for brunch with the girls! Featuring spaghetti straps, a sweetheart neckline, and a front slit accent on crepe knit fabric with a moderate stretch. Complete the look in heeled mules and hoops.
Fit & Features
- Sleeveless, spaghetti straps
- Sweetheart neckline, slit accent
- Floral print
- Midi hem
- Crepe knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4305
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Steal The Spotlight Leopard Slit Midi Dress
Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, flowy silhouette
- Front slit
- Leopard print
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4306
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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