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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Hauntingly Stylish Mesh Mini Dress
You'll look hauntingly stylish in this form-hugging mini dress! It features a sleeveless crew neckline, tank shoulder straps, and a mini-length bodycon silhouette. The sheer mesh fabric includes a full lining and showcases an all-over spiderweb print, perf for spooky season! Wear this dress with sleek hoop earrings.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Short, form-hugging silhouette
- Sheer mesh fabric, full knit lining, moderate stretch
- Spiderweb pattern
- Runs true to size
Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.
Style Number/Barcode: 05102-4141
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Silhouette Long Sleeve Maxi Dress
Create a chic silhouette in this curve-hugging maxi dress. It features a crew neckline, long fitted sleeves, a stylish cutout at the lower back, and a floor-length form-hugging fit with a side slit. Style this dress with clear heels.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Cutout at the lower back
- Floor-length, form-hugging fit
- Side slit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4137
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Next Level Midi Dress
Take your look to the next level with a midi dress that demands drama! The dress features a crew neckline, long sleeves, a high side slit, and a midi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Crew neckline
- Long fitted sleeves
- High side slit
- Midi-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4138
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Moves Ruched Mini Dress
Make chic moves in this curve-hugging mini dress! It features a trendy mock neckline, long sleeves, a sultry cutout above the bust, ruched detailing down the sides, and a short, form-fitting silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Cutout above the bust
- Ruching down the sides
- Mini-length, form-fitting silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4144
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Chic Ruched Mini Dress
Elevate your everyday look with this trendy-chic mini dress. It features a wide boat neckline, long fitted sleeves, a partially open back with a V-design, back ruched detailing, and a short, curve-hugging silhouette. Complete the outfit with over-the-knee boots.
Fit & Features
- Wide boat neckline
- Long fitted sleeves
- Open back, V-design
- Ruched detailing down the back
- Mini-length, bodycon silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4134
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Daydream Mesh Mini Dress
You'll look like such a daydream in this trendy tie-dye mini dress! It features a sleeveless scoop neckline, spaghetti straps, a twist-back design, a short, curve-hugging silhouette, and a subtle all-over tie-dye print in pretty pastel hues. Style this dress with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Twist-back design
- Mini-length, form-hugging fit
- Mesh fabric, tie-dye print, pastel hues
- Runs true to size
Style Number/Barcode: 05102-4131
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fabulous Floral Puff Sleeve Mini Dress
Keep your look fresh and fab in this adorable floral printed mini dress! It features a sweetheart neckline with a tie at the bust, short puff sleeves, and a short, curve-hugging silhouette. Style this dress with strappy sandals and chic sunnies.
Fit & Features
- Sweetheart neckline, tie at the bust
- Short puff sleeves, elastic cinched hems
- Mini-length, form-hugging fit
- Brushed knit fabric, plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-4125
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Summer Vibes Maxi Dress
This adorable maxi dress brings those trendy summer vibes! It features a sleeveless square neckline, spaghetti straps that lead to a cross-back lace-up design, a high waist seam, and a floor-length fitted silhouette with a thigh-high front slit. The brushed knit fabric has a cool all-over tie-dye print. Style this dress with strappy sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cross-back lace-up design
- High waist seam
- Floor-length fitted silhouette, front slit
- Brushed knit fabric, moderate stretch, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-4130
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Cutie Denim Tube Dress
Keep it chic with a tube dress that is perf to dress up for your next brunch date! The dress features a sleeveless square neckline, belt loops, side pockets, 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 a faux leather belt and mules.
Fit & Features
- Sleeveless square neckline
- Belt loops
- Side pockets
- Mini length silhouette
- Denim fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4128
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry-Chic Style Mini Dress
Elevate your style with this sultry-chic mini dress! It features a sleeveless deep V-neckline, spaghetti straps, sexy cutouts at the waist, and a short, form-hugging fit that will hug your curves. Complete the look with sleek earrings and cute mules.
Fit & Features
- Sleeveless deep V-neckline
- Spaghetti straps
- Cutouts at the waist
- Mini-length, form-hugging silhouette
- Ribbed knit fabric, smooth knit lining
- Runs true to size
Style Number/Barcode: 05102-4119
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blooming Beauty Ditsy Floral Cutout Mini Dress
Let your beauty bloom with a gorge mini dress that reveals your sweet side! The dress features a ditsy floral print, a sleeveless V-neckline, a ruched drawstring at the center, spaghetti straps, a cutout at the midriff, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a denim jacket.
Fit & Features
- Ditsy floral print
- Sleeveless V-neckline
- Ruched drawstring at the bodice
- Spaghetti straps
- Cutout at midriff
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4126
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Getaway Mesh Mini Dress
Get ready for your island getaway in this adorable mesh mini dress! It features a sleeveless square neckline, adjustable spaghetti straps, ruched detailing, a short, curve-hugging silhouette, and an all-over tropical palm leaf print. Style this dress with strappy sandals.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruching
- Mini-length, form-hugging fit
- Sheer mesh fabric, tropical palm leaf print, knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4133
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The One Eyelet Mini Dress
This eyelet dress is the one for you, babe! The dress features an eyelet pattern, a scoop neckline with a tie-bust accent, spaghetti straps, ruffle trim at the bodice, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless scoop neckline, tie-bust accent
- Spaghetti straps
- Ruffle trim at bodice
- Mini length silhouette
- Eyelet pattern
- Lightweight woven fabric, lined knit fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4122
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Eyes On Me Floral Eyelet Maxi Dress
Draw all eyes on you in this bold maxi dress! The dress features a vibrant floral print, an eyelet pattern, a sleeveless V-neckline, spaghetti straps, dual waist cutouts, and a maxi-length silhouette with a flared hem. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes a mini skirt-length knit lining. Complete look with sandals and hoops.
Fit & Features
- Floral print
- Sleeveless V-neckline, spaghetti straps
- Dual waist cutouts
- Eyelets
- Maxi length silhouette
- Lightweight woven fabric, mini skirt knit lining
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4123
Category Name: Casual Dresses
Price: $9.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Trendy Cutout Mini Dress
Keep your look trendy and chic in this ribbed knit mini dress that is a summer staple! It features a sleeveless crew neckline, a front O-ring accent, dual waist cutouts, and a short, curve-hugging silhouette. Style this dress with sneakers for everyday wear, or cute mules for date night.
Fit & Features
- Sleeveless crew neckline
- Front O-ring detail
- Dual waist cutouts
- Mini-length, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4115
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Vibes Ribbed Knit Maxi Dress
Achieve those effortless, casual-chic vibes with this ribbed knit maxi dress. It features a sleeveless scoop neckline, spaghetti straps, and a curve-hugging silhouette with a cute side slit to show some leg. Style this dress with sneakers for every day, or heels for date night.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Form-hugging fit
- Side slit
- Lined ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4118
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off To The Tropics Maxi Dress
Head off to the tropics in a maxi dress that instantly puts you in vacay mode! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, and a maxi silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross back
- Tropical print
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4104
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Burst Tie Dye Mini Dress
Add a burst of color to your look with this fab mini dress! The dress features a tie-dye print, sleeveless square neckline, bungee straps that cross at the back, lace-up straps, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear heels.
Fit & Features
- Sleeveless square neckline
- Bungee straps, cross at the back
- Lace-up straps
- Mini length silhouette
- Tie-dye print
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4114
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet For The Summer Babydoll Dress
Sweet and chic, this babydoll dress is perf for the summer season. It features a square neckline, three-quarter length puff sleeves with cute ruffled hems, a high waist seam, and a short, flowy, flared-out silhouette. Style this dress with a trendy shoulder bag and mules for a weekend brunch.
Fit & Features
- Square neckline
- Three-quarter length puff sleeves, ruffled elastic cinched hems
- Stretchy smocked back detail, high waist seam
- Mini-length silhouette
- Flowy, flared-out fit
- Twill fabric, woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4109
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Chic Smocked Maxi Dress
Capture those effortlessly chic vibes in this maxi dress! The dress features a square neckline, short sleeves, and a smocked bodice. The maxi length silhouette features a button-down center and a mini skirt length lining. The dress is composed of a smocked knit fabric and lightweight woven fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.
Fit & Features
- Square neckline, short sleeves
- Smocked bodice
- Button-down center
- Maxi length silhouette
- Mini skirt length knit lining
- Smocked knit, lightweight woven fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4113
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Raise The Stakes High Slit Cutout Dress
Raise the stakes in a bold maxi dress that dares to stun! The dress features a sleeveless halter neck with a racer bust, a sexy cutout at the midriff, ruching at the waist, and a high-side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops.
Fit & Features
- Halter neck with racer bust
- Cutout at the midriff
- Ruching at waist
- High side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4108
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tiki Island Escape Cutout Mini Dress
Create an island escape look with a mini dress that is perf for your next getaway! The dress features a plunging sleeveless v-neckline, halter neck ties, a sexy midriff cut-out, a tropical palm leaf print, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Halter neck ties
- Midriff cutout
- Tropical palm leaf print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4106
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Summer Vibes Maxi Dress
Get those chic sultry vibes this summer in this stunning maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts, a floor-length, fitted silhouette, and an all-over tropical floral print. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual waist cutouts
- Floor-length, form-hugging silhouette
- Knit fabric
- Tropical floral print
- Runs true to size
Style Number/Barcode: 05102-4112
Category Name: Casual Dresses
Price: $6.97 $40.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Sunsets Asymmetrical Midi Dress
Take in those tropical vibes with a midi dress that will have you vacay-ready! The dress features a tropical palm leaf print, a sleeveless scoop neckline, adjustable spaghetti straps that cross at the back, and an asymmetrical hem. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with hoops and sandals.
Fit & Features
- Tropical palm leaf print
- Sleeveless scoop neckline
- Adjustable spaghetti straps, cross at back
- Midi length silhouette
- Asymmetrical hem
- Smooth knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4111
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale