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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Set For Vacay Tropical Floral Strapless Midi Dress
You'll be set for vacay in this strapless knit midi dress featuring a large tropical floral print for a bold allure. The form-hugging silhouette will flaunt your gorgeous curves.
Fit & Features
- Sleek knit fabric with full-length knit lining, high stretch
- Large tropical floral print
- Strapless straight-across neckline, no-slip strip
- Midi-length hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-6097
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blissful Cutie Eyelet Bodycon Midi Dress
Enter every room like a blissful cutie in this eyelet bodycon midi dress perfect for brides-to-be or brunch!
Fit & Features
- Eyelet fabric lined with stretchy knit
- Square neckline, ruffle trim, bust tie
- Wide shoulder straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6098
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slay All Day Paisley Mesh Maxi Dress
Look good from every angle—this paisley mesh dress understood the assignment. The halter square neckline and high side slit bring all the heat for a night out or glam rooftop vibes.
Fit & Features
- Paisley print, mesh-lined fabric, moderate stretch
- Halter square neckline with spaghetti straps
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6099
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
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Ravishing Florals High-Slit Ruched Maxi Dress
Usher in romance in a maxi dress that features a sleeveless square neckline with spaghetti straps, an abstract floral pattern, ruching throughout to enhance curves, and a high side slit. Complete the look with block heels that will have you ready for your next brunch date!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Spaghetti straps
- Abstract floral pattern
- Ruching
- High side slit
- Maxi length hem
- Runs true to size
Style Number/Barcode: 05101-3859
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Trend Striped Knit Long Sleeve Mini Dress
This trendy striped knit mini dress features a scoop neckline, long fitted sleeves, an open lower back accent, and a short bodycon silhouette to hug your curves. Perfect for casual chic styling, pair with knee-high boots.
Fit & Features
- Striped ribbed knit fabric
- Scoop neckline
- Long fitted sleeves
- Open lower back
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2119
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweetest Outing Tie Back Ruffled Skater Mini Dress
Have the sweetest look in this tie back ruffled skater dress at bridal showers or graduations!
Fit & Features
- Woven fabric lined with stretch knit
- Sweetheart neckline with bust tie
- Adjustable spaghetti straps
- Tie-back cutout design, zipper and hook-eye closure
- Skater ruffled silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6101
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feel The Sunshine Sweetheart A-Line Mini Dress
Step into the sunshine in this adorable sleeveless mini dress! With a captivating sweetheart neckline and hoop insert, this dress flatters your figure in an A-line silhouette and mini-length hem.
Fit & Features
- Woven fabric, stretchy knit lining
- Sweetheart neckline with hoop insert
- Wide shoulder straps
- Back zipper closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6100
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Turn Heads Abstract Print Strapless High Slit Maxi Dress
Unveil a chic allure in this lined airy mesh maxi dress designed with an eye-catching abstract print to turn heads. It features a strapless straight-across neckline, a high-cut side slit to reveal some leg, and a fitted silhouette on the maxi-length hem.
Fit & Features
- Sheer mesh fabric with soft brushed knit lining, plenty of stretch
- Abstract print
- Strapless straight neckline
- High side slit
- Maxi-length fitted silhouette
- Runs true to size
Style Number/Barcode: 05102-6105
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Cute Tie-Front Pleated Mini Dress
With just the snap of a finger you'll look simply cute in this tie-front pleated mini dress designed to make a statement!
Fit & Features
- Woven fabric, woven lining
- Square neckline with dual tie-front
- Spaghetti strap ties, side zipper and hook-eye closure
- Drop waist seam
- Fitted silhouette
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000119
Category Name: Casual Dresses
Price: $7.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cosmic Chic Tie-Dye Knit Midi Dress
The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe.
Fit & Features
- Ribbed knit fabrication
- Scoop neckline
- Long sleeves
- Tie-dye pattern
- Center slit at back of hem
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2132
Category Name: Casual Dresses
Price: $6.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Kiss The Sun Tropical Lace-Up Slit Maxi Dress
Sipping a mai tai oceanside has never looked cuter in this tropical maxi dress! Made to turn heads, this maxi dress boasts a sexy lace-up back, form-hugging silhouette that shows off your curves, and a high front slit giving major allure.
Fit & Features
- Tropical print, mesh-lined fabric
- V-neckline
- Spaghetti straps
- Lace-up back
- Form-hugging silhouette, high front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6103
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft And Chic Ribbed Knit Off-The-Shoulder Mini Dress
Soft and chic, this mini dress is made with ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder straight neckline with a long fold-over design for a trendy look and a short bodycon silhouette to highlight your curves.
Fit & Features
- Ribbed knit fabric
- Off-the-shoulder straight neckline
- Long fold-over design
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-2259
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Falling For You Tropical Floral Slit Maxi Dress
Get the golden hour glow in this tropical floral maxi dress while on vacation! Featuring a chic square halter neckline and a form-hugging fit with a high side slit, this dress beautifully accentuates your silhouette.
Fit & Features
- Tropical floral print, mesh-lined fabric
- Square halter neckline, adjustable spaghetti straps
- Criss cross back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6113
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Hidden Treasure Lace-Up Shell Accent Midi Dress
Discover your new signature look with this irresistible midi dress featuring a unique shell accent neckline, lace-up back offers undeniable allure, and a sultry side slit creates movement.
Fit & Features
- Texture knit fabric, moderate stretch, stretchy knit lining
- V-neckline with shell accent trim
- Spaghetti straps
- Lace-up back
- Side slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6119
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Destination Summer Tropical Linen Mini Dress
This cute mini dress was made for summer vacays featuring a contrast tropical print on lightweight linen fabric. The lace-up strappy back design offers a customized fit and a head-turning vibe.
Fit & Features
- Linen-blend woven fabric, woven lining
- Tropical print
- Sleeveless square neckline
- Spaghetti straps
- Open cross-back lace-up strappy design
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6115
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Girlie Halter Bead Crochet Mini Dress
Your next getaway calls for this crochet mini dress! This dress has a stunning halter bead neckline that adds a touch of boho, a cutout accent, and a flattering bodycon silhouette.
Fit & Features
- Crochet lined fabric
- Halter beaded neckline, spaghetti strap ties
- Padded bra cups
- Back zipper hook-eye closure, lower ruched seam
- Cutout front accent
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6116
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spring Fling V-Neck Paisley Skater Dress
Swing into spring in this paisley skater dress for an adorable look all season! With a flirty halter V-neck and a flowy mini-length hem, this dress is ready for brunch or day dates.
Fit & Features
- Paisley print, chiffon fabric, woven lining
- Halter V-neck
- Spaghetti strap ties with tassels
- Stretchy smocked bodice
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5994
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Maui Nights Strapless Tropical Midi Dress
Booked a vacation? This tropical midi dress is here to make you look stylish for your getaway! Designed with a flattering bodycon silhouette and side slit for effortless sultriness.
Fit & Features
- Tropical print, mesh knit-lined fabric
- Strapless neckline
- Bodycon silhouette
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6120
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Hottie Tropical Halter Slit Maxi Dress
Look hot to trot around the island on vacation in this tropical maxi dress! This stunning maxi features a crisscross halter neckline for a touch of elegance and a front slit to show off those curves.
Fit & Features
- Tropical palm print, stretchy knit fabric, bust knit lining
- Crisscross halter neckline, beaded
- Front slit
- Curve-hugging fit
- Flowy maxi length hem
- Runs true to size
Style Number/Barcode: 05102-6117
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Era Woven A-Line Midi Dress
Enter your effortless era in this woven A-line midi dress featuring a stretchy smocked bodice, hidden side pockets, and a pleated flowy silhouette with a side slit.
Fit & Features
- Poplin smooth cotton woven fabric with full-length woven lining
- Sleeveless square neckline, adjustable spaghetti straps
- Stretchy smocked bodice
- V-shaped waist
- Pleating, hidden side pockets
- Midi-length flowy A-line silhouette, high side slit
- Runs true to size
Style Number/Barcode: 05102-000001
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Into The Sun V-Neck Maxi Dress
Sun goddess maxi dress boasting a V-neckline with a unique metal accent and a body-skimming silhouette. Style with strappy sandals for a sunset dinner.
Fit & Features
- Textured knit fabric, soft knit stretchy lining
- V-neckline with metal accent
- Spaghetti straps
- Body-skimming silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000002
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Girl Abstract Halter Slit Maxi Dress
Need an unforgettable look? This abstract maxi dress will be the perfect companion for rooftop cocktails and parties, boasting a sultry halter neckline, cutout bodice, and high slit giving major sultry energy.
Fit & Features
- Abstract print, stretchy knit fabric, short knit stretch lining
- Halter neckline with tie straps, hoop insert
- Cutout bodice
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000003
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Twist Ribbed Knit Mini Dress
Add a stylish twist to your look with a mini dress that features a plunging sweetheart neckline with a twisted accent at the center and fitted long sleeves. Complete look with knee-high boots.
Fit & Features
- Ribbed knit fabrication
- Sweetheart neckline
- Twist accent at the center of a bust
- Fitted long sleeves
- Mini length hem
- Runs true to size
Style Number/Barcode: 06005-2182
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Days A-Line Midi Tube Dress
Effortless days call for this woven midi tube dress designed with a smocked bodice with a geometric pattern and a flowy pleated A-line silhouette. Perfect for weekend plans, style with strappy sandals.
Fit & Features
- Poplin cotton woven fabric
- Strapless sweetheart neckline
- Smocked bodice, geometric pattern
- High-rise waist
- Side pockets
- Midi-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000007
Category Name: Casual Dresses
Price: $11.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free