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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Trend Moment Lace-Up Bodycon Midi Dress
Have your trending moment in this midi dress! It's designed to hug your curves in a bodycon silhouette while the front lace-up adds a playful touch to your day or night look.
Fit & Features
- Knit fabric with moderate stretch
- Square neckline
- Lace-up front bust
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6072
Category Name: Casual Dresses
Price: $9.97
Availability: Out of Stock
Product Badge:- Ships Free
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Sporty-Chic Knit Mini Dress
Get a sporty-chic style with this adorable knit mini dress. It features a collared V-neckline with a zip-front, short sleeves, and a mini-length, curve-hugging silhouette. The lined knit fabric offers plenty of stretch. Complete the look with trendy mules.
Fit & Features
- Collared V-neckline, zip-front
- Short sleeves
- Mini-length hem
- Form-hugging fit
- Lined knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4152
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Denim Dreams Lace-Up Mini Dress
Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, 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 scoop neckline
- Spaghetti straps
- Lace-up back, lower back zipper and hook and eye closure
- Vertical seams
- Mini-length silhouette
- Denim fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4089
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ravishing Florals Ruched Mini Dress
Stun with ravishing florals in a pretty mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, dual ruching that runs from the bodice to hem, a ditsy floral print, and a mini-length silhouette. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Dual ruching
- Ditsy floral print
- Mini length silhouette
- Lined mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4151
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sweet Ruffled Cutout Skater Dress
Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.
Fit & Features
- Off-the-shoulder neckline
- Smocked bodice with a ruched drawstring
- Long sleeves, elastic cinched hems
- Cutout at the midriff
- Tiered ruffle skater skirt
- Gauze knit fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2486
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Vibes Off-The-Shoulder Floral Mini Dress
Bring those sweet vibes with a pretty mini dress that is perf for your next date night! The dress features a ditsy floral print, an off-the-shoulder neckline, a sweetheart bust with a mini tie-front, short puff sleeves, 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
- Off-the-shoulder neckline
- Sweetheart bust, mini tie-front
- Short puff sleeves, ruffled hems
- Mini-length silhouette
- Brushed knit fabric, side ruched detailing
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4154
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Casual Glam Ribbed Knit Maxi Dress
Keep it casually glam with a maxi dress that is perf to dress up or down for brunch! The dress features a sleeveless V-neckline, a cute tie-front, adjustable spaghetti straps, a button-down front, and a maxi-length silhouette accented with a high center slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a floppy hat.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, tie-front
- Button-down front
- Maxi-length silhouette, high center slit
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1347
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hooked In Denim Mini Dress
Get hooked in with this cute mini dress that is part glam, part casual! The dress features a strapless sweetheart neckline, hook and eye front closures, corset seams, 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
- Strapless sweetheart neckline
- Hook and eye front closures
- Corset seams
- Mini-length silhouette
- Denim knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4081
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What's The Scoop Ribbed Knit Mini Dress
Serve up a stylish look with a pretty mini dress! The dress features a sleeveless scoop neckline, a tie-front at the bust, bungee spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with plenty of stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Tie-front at the bust
- Bungee spaghetti straps
- Mini-length silhouette
- Ribbed knit fabric
- Form-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4162
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Boho Vibes Maxi Dress
Bring on the stunning boho vibes with this effortlessly chic maxi dress. It features a sleeveless V-neckline, spaghetti straps, a tie-front bust with a sexy waist cutout, and a curve-hugging floor-length silhouette with a sultry thigh-high side slit. Style this dress with trendy earrings and cute mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-front bust, waist cutout
- Floor-length, form-hugging fit
- High side slit
- Knit fabric, paisley print
- Runs true to size
Style Number/Barcode: 05102-4159
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Girly Vibes Gingham Babydoll Dress
Keep it super girly with a pretty babydoll dress that brings those good vibes this season! The dress features a sweetheart neckline, quarter-length balloon sleeves, a gingham print, and flared mini-length silhouette with a ruffled hem. The dress is composed of cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with sandals.
Fit & Features
- Sweetheart neckline
- Quarter-length balloon sleeves
- Gingham print
- Ruffles
- Mini length silhouette
- Cotton knit fabric, additional knit lining
- Relaxed fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-3064
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Sunsets Maxi Dress
Your dream vacation is calling! Pack this stunning tropical floral printed maxi dress for a gorgeous look. It features an off-the-shoulder square neckline, a fitted smocked bodice, short ruffled sleeves, a tie-front accent to highlight the waist, and a flowy, floor-length silhouette with a wrap-front design. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Off-the-shoulder square neckline
- Fitted smocked bodice
- Short ruffled sleeves
- Tie-front detail
- Flowy, floor-length silhouette, wrap-front design
- Woven fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-4068
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Barely Blushing Floral Mini Dress
Soft girl, but make it sultry. This floral mini dress clings in all the right ways, with delicate straps and a dreamy texture that feels flirty but effortless!
Fit & Features
- Floral print, burnout texture, mesh fabric, stretchy knit lining
- Scoop neckline
- Adjustable spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000165
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keepin' It Cute And Casual Denim Dress
Keep your everyday look cute and casual in this must-have denim dress! It features a sleeveless square neckline, thin shoulder straps, a complete button-down front, and a short, curve-hugging silhouette. Style this dress with sneakers and chic shades.
Fit & Features
- Sleeveless square neckline
- Thin shoulder straps
- Complete button-down front
- Mini-length, form-hugging fit
- Denim fabric
- Runs true to size
Style Number/Barcode: 05102-0500
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrapped In Florals Chiffon Skater Dress
Wrap yourself in a fab floral dress this season for your next brunch! The dress features a floral print, plunging V-neckline, ruffled cap sleeves, an open back with a tie-back strap, and a skater silhouette with an asymmetrical ruffled trim. The dress is composed of a semi-sheer chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with sandals and duster earrings.
Fit & Features
- Wrap V-neckline
- Ruffled cap sleeves
- Open back with tie back ties
- Skater silhouette
- Ruffle trim
- Floral print
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1103
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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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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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
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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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Carefree Bohemian Chic Cutout Maxi Dress
Channel a carefree vibe with a maxi dress that is so bohemian chic! The dress features a bohemian print, a sleeveless V-neckline, spaghetti straps, dual cutouts at the waist, and a maxi-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit. Complete look with sandals and tassel earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual cutouts at the waist
- Knit fabric, bohemian print
- Maxi-length silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4063
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Dream Lace-Up Maxi Dress
Get carried away in this tropical maxi dress that will have you ready for that cabana life! The dress features a tropical floral print, a sleeveless V-neckline, a double row of spaghetti straps that cross at the back, a lace-up back, and a maxi-length 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 and hoops.
Fit & Features
- Tropical floral print
- Sleeveless V-neckline
- Double-row of spaghetti straps, cross at back
- Lace-up back
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-2104
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bold Stunner Cutout Mini Dress
Create a bold moment in a chic mini dress that stuns! The dress features a scoop neckline, short puff sleeves, dual cutouts at the waist, and an A-line silhouette. The dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Complete look with slides and hoops.
Fit & Features
- Scoop neckline
- Short puff sleeves
- Dual cutouts at the waist
- Mini length silhouette
- Lightweight woven fabric
- Form hugging fit, runs true to size
Style Number/Barcode: 05102-4188
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale