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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Total Sweetheart Floral Mini Dress
Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.
Fit & Features
- Short sleeves
- V neckline
- Ruching at the bust with a front drawstring
- Small cutout under the bust
- Ruching down the sides
- Mini-length, form-hugging fit
- Unlined knit fabric with plenty of stretch
- Floral print
- Runs true to size
Style Number/Barcode: 05102-0679
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Smocked Floral Mini Dress
Bring a sweet vibe to your spring style with this adorable floral mini dress! It features an off-the-shoulder square neckline, short ruffle sleeves, and a curve-hugging, mini-length silhouette with a smocked design. Complete the look with hoop earrings and new heels.
Fit & Features
- Off-the-shoulder square neckline
- Short ruffle sleeves
- Short, form-hugging fit
- Floral print
- Chiffon fabric, smocked design
- Runs true to size
Style Number/Barcode: 05102-0339
Category Name: Casual Dresses
Price: $20.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Flirt Ditsy Floral Skater Dress
You'll be a major flirt in this adorable ditsy floral dress! It features tie-shoulder spaghetti straps, a V neck and back, a high waist seam, and a flowy skater silhouette. The floral printed knit fabric offers plenty of stretch. Complete your outfit with gold hoop earrings and strappy sandals.
Fit & Features
- Tie-shoulder spaghetti straps
- V neck and back
- Elastic high waist seam
- Short skater silhouette
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-0222
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Floral Ruffled Chiffon Skater Dress
Get an effortlessly romantic look for a daytime date with this floral chiffon skater dress. It features ruffle detail shoulder straps, a wrap-front V neckline, a backless design with a thin tie-back accent, a high waist with a tie-front, and a flowy skater silhouette with tiered ruffle detailing. Complete the outfit with hoop earrings and a new purse.
Fit & Features
- Ruffle detail shoulder straps
- Wrap-front V neckline
- Open-back design, zipper closure, tie-back closure
- High waist, tie-front
- Short skater silhouette, ruffle details
- Floral chiffon fabric
- Runs true to size
Style Number/Barcode: 05102-0454
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Chic Ruffled Eyelet Mini Dress
You'll be looking too chic with a mini dress that brings all those cute deets! The dress features an elastic square neckline, short puff sleeves, a lace-up front, an eyelet design, and a mini-length silhouette with a ruffled hem. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Elastic square neckline, puff short sleeves
- Front lace-up
- Form-fitting, mini-length, ruffle hem
- Eyelet lace fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1163
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Going Out Strapless Lace Mini Dress
Occasions made easy! This strapless lace mini dress is here to make you stand out at brunch or parties with a twirl-worthy hanky hem.
Fit & Features
- Lace fabric lined with stretchy knit
- Strapless neckline
- Side ruched seams, fitted bodice
- Flared hanky mini length hem
- Runs true to size
Style Number/Barcode: 05102-000015
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Free-Spirited Darling Tie-Dye Mini Dress
Channel your boho side with a tie-dye dress that keeps it chic and casual. The dress features a sleeveless V-neckline with a halter neck tie, a tie-dye pattern, an open back with tie-back straps, and a mini-length A-line silhouette with tiered ruffles. The dress is composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Halter neck-tie
- Tie-dye pattern
- Open back with tie back straps
- Mini length A-line silhouette
- Ruffles
- Lined linen, relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1952
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Brunch Babe Smocked Floral Dress
This adorable floral dress will have you looking so cute for brunch with the girls! It features a sleeveless bodice with tie shoulder spaghetti straps, a square neckline, a stretchy smocked bust, and a high waist with a flowy short skirt with an A-line silhouette. The floral printed dress is composed of a lightweight woven fabric with a stretchy skirt lining. Style this dress with a denim jacket and wedges.
Fit & Features
- Tie shoulder spaghetti straps
- Square neckline
- Stretchy smocked bust
- High waist leading to a flowy short skirt
- A-line silhouette
- Floral-printed woven fabric
- Stretchy knit skirt lining
- Runs true to size
Style Number/Barcode: 05102-0441
Category Name: Casual Dresses
Price: $20.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Cutie Linen Skater Dress
Get a casual cute look in this lightweight linen skater dress. It features adjustable spaghetti straps, a lined crochet bodice with a V neckline, an open back with a tie closure, and a flowy, skater silhouette. The gauze and linen fabric has a knit lining. Complete your outfit with adorable wedges and a chic shoulder bag.
Fit & Features
- Adjustable spaghetti straps
- Lined crochet bodice with a V neckline
- Open back with a tie closure
- Short skater silhouette
- Gauze and linen fabric with no stretch
- Knit lining
- Runs true to size
Style Number/Barcode: 05102-0233
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Ruffles Chiffon Dress
Charm them all with romantic ruffles in this super gorge mini dress!
Fit & Features
- Plunging V-Neckline | Ruffle Trim
- Adjustable Spaghetti Straps | Cross-Back
- Multi-Tiered Ruffle Accents
- Lined Chiffon Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0498
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Vibes Cutout Maxi Dress
Rock those basic vibes with a maxi dress that keeps its lowkey. The dress features a sleeveless scoop neckline, adjustable spaghetti straps, a sexy lower back cutout, and a maxi-length silhouette. The dress is composed of a lined cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with t-strap sandals.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Lower back keyhole
- Maxi length silhouette with a high side slit
- Cotton knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1961
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Must-Have Everyday Ribbed Knit Dress
This must-have ribbed knit dress is perf for an everyday outfit! It features bungee spaghetti straps, a square neckline, ruching, and dual drawstrings at the hem. Style the dress as a mini and pair it with sneakers for a casual brunch with friends, or make the dress a midi length and style with clear heels for a date night.
Fit & Features
- Bungee spaghetti straps
- Square neckline
- High waist seam and side ruched detailing
- Dual drawstrings
- Style as a mini or midi dress
- Ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1455
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tie Dye Ruched Mini Dress
Keep it ruched and stylish with a dress that channels those retro vibes. The dress features a sleeveless square neckline, spaghetti straps, dual drawstrings, a tie-dye print, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Dual drawstrings
- Tie-dye print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1438
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All My Heart Ruched Mini Dress
Give all your love with this fluttery mini dress! The dress features an off the shoulder neckline with a sweetheart bust, a fab lace-up front, off the shoulder flutter sleeves, and a ruched body. The dress is composed of a double-lined cotton-blend fabric that offers a form hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Off the shoulder neckline
- Lace-up front
- Off the shoulder flutter sleeves
- Ruched body
- Mini length silhouette
- Double-lined cotton blend fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-1124
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Chic Ruched Knit Mini Dress
Keep your style sweet and chic in this adorable ruched knit mini dress! It features a sweetheart neckline with a mini keyhole cutout and tie at the bust, short sleeves, ruching down the sides, and a short, curve-hugging silhouette. Complete your look with wedges and a cute handbag.
Fit & Features
- Sweetheart neckline
- Mini keyhole cutout and tie at the bust
- Short sleeves with cinched hems
- Ruching
- Mini-length, form-hugging fit
- Lined stretchy knit fabric
Style Number/Barcode: 05102-1123
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love At First Sight Mini Dress
With you in this adorable ditsy floral dress, it will be love at first sight. The dress features thin ruffle shoulder straps, a V neckline with subtle ruching, and a short, curve-hugging silhouette. The lightweight knit fabric offers plenty of stretch. Complete your look with a classic denim jacket and sneakers.
Fit & Features
- Thin ruffle shoulder straps
- V neckline with ruching
- Mini-length, form-hugging fit
- Knit fabric with plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-1429
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Charm Puff Sleeve Floral Mini Dress
Keep it charming and chic in a floral mini dress that keeps you looking gorge! The mini dress features an elastic square neckline, short puff sleeves, a ditsy floral 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 mules.
Fit & Features
- Square neckline
- Short puff sleeves
- Ditsy floral print
- Mini length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-0787
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set It Off Ruched Mini Dress
Set off your look with a dress that showcases your luxe style! The dress features a sleeveless square neckline, tank straps, a ruched side seam, 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 mules.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Ruched side seam
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1120
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love At First Bloom Ditsy Floral Mini Dress
Fall headfirst for this floral dress that showcases your sweet side. It features adjustable spaghetti straps, a ruffled sweetheart neckline with a center cutout and tie-front, a stretchy smocked back, and a short, curve-hugging fit. Complete your look with strappy sandals and a cute handbag.
Fit & Features
- Adjustable spaghetti straps
- Ruffled sweetheart neckline
- Center cutout and tie-front
- Stretchy smocked back
- Mini-length, form-hugging fit
- Sheer chiffon fabric with a ditsy floral print, woven lining
- Runs true to size
Style Number/Barcode: 05102-0756
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Sweetheart Floral High Slit Maxi Dress
Show off your sweet side with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a floral print, and a maxi length silhouette accented with a high side slit. The dress is composed of a smooth knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Floral print
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 05102-0773
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Energy Strapless Floral Mesh Maxi Dress
Bring major energy in this strapless floral mesh maxi dress design to flaunt your figure in a bodycon fit and show some skin with a high-side slit. Pair with mules.
Fit & Features
- Floral print, mesh fabric, soft and stretchy knit lining
- Strapless neckline
- High-side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-000780
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: PLUM, PLUM-2
Available Size: XS, S, M, L, XL
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Romantic Ruched Knit Maxi Dress
Get a gorgeous look for a romantic date night in this sultry ruched maxi dress. It features spaghetti straps, a square neckline, ruched side detailing, and a maxi length with a high side slit. The knit fabric offers plenty of stretch and provides a curve-hugging fit. Style this dress with a new pair of earrings and strappy heels.
Fit & Features
- Spaghetti straps
- Square neckline
- Ruched side detailing
- Maxi length
- High side slit
- Stretchy knit fabric with a short lining
- Form-hugging fit
Style Number/Barcode: 05102-0331
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Fab Ruffled And Smocked Mini Dress
Keep it so fab in a smocked dress that keeps your look effortlessly cute! The dress features an off-the-shoulder neckline, a sweetheart bust with a tie-front, and short sleeves with a ruffled hem. The back features a stretchy smocked fabric to provide a relaxed fit. The dress is composed of a lined lightweight woven fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Off-the-shoulder neckline
- Short sleeves with a ruffled hem
- Sweetheart bust with a tie-front
- Smocked back
- Lightweight woven fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1106
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Stunner Puff Sleeve Mini Dress
You'll be a total stylish stunner in this adorable floral mini dress! It features short puff sleeves, a square neckline with a front keyhole cut out and tie at the bust, and a short, curve-hugging silhouette. The all-over floral print makes the dress a perfect option for brunch dates and shopping trips with your girls. Complete the look with a pair of cute wedges.
Fit & Features
- Short puff sleeves, elasticized hems
- Elastic square neckline
- Front keyhole cut out and tie at the bust
- Back zipper, hook and eye closure
- Mini-length, form-hugging fit, moderate stretch
- Floral print
- Smooth knit fabric, fully lined
- Runs true to size
Style Number/Barcode: 05102-4339
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale