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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Everyday Ease: Casual Dresses for Transitional-Weather Plans
From weekend brunches to spontaneous coffee runs, Windsor’s casual dresses deliver easygoing style with just the right amount of polish. These effortlessly chic looks move with you—whether you’re off to the farmers’ market or catching golden hour with friends. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler days. Slip into playful mini dresses, flowy midi styles, or long casual dresses in warm neutrals, jewel tones, and classic plaids. T-shirt and tunic dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.
Chic from Day to Night
Swap sneakers for ankle boots to take your favorite midi dress from errands to evening hangs. A flowy maxi in nuetral or black adds relaxed elegance—just add a faux leather jacket and heeled booties for an effortless finish.
Ready to refresh your everyday looks? Explore Windsor’s full collection of casual dresses online, in-app, or in-store.
What Makes a Dress Casual?
Casual dresses are defined by their effortless styling, comfortable fabrics, and laid-back details. Fabrication plays a key role—soft knits, cotton blends, and breezy silhouettes naturally create an easygoing look. Prints like ditsy florals or neutral-tone patterns, such as snake print, also make great everyday choices. Knit and sweater dresses are perfect for relaxed settings, whether you're heading to work or dressing up for a casual date night.
Styling is just as important in making a dress feel casual. Swap heels for sneakers, lug boots, or strappy sandals to instantly dress down your look. Layering is another effortless way to create a relaxed aesthetic—throw on a denim jacket, cropped sweater, or oversized cardigan for a cool, laid-back vibe. Details like drawstrings, button fronts, and tie accents also add to the casual appeal. Accessories, makeup, and hair styling can further influence the look, so opt for dainty jewelry, natural waves, or a simple ponytail to complete your effortlessly stylish outfit.
How Do I Style a Dress Casually?
Styling a dress casually is all about choosing relaxed layers and accessories that balance comfort with fashion. Denim jackets, graphic tees, scrunchies, crossbody bags, and sneakers all contribute to an effortlessly cool aesthetic. Try pairing a ruched mini dress with a lariat necklace and chunky sneakers for a sporty yet chic look. A basic knit midi dress layered under a cropped denim jacket with slides is perfect for a casual-chic feel.
For road trips or weekend getaways, maxi and midi dresses offer an easy styling solution. Layer a lightweight sweater over a flowy maxi or knot a t-shirt at the waist for a trendy, carefree vibe. Combat boots can add an edgy touch, while simple strappy sandals keep the outfit light and airy. No matter your style, Windsor has a versatile collection of casual dresses and must-have accessories to complete your look. Need styling help? Visit us in-store, and our expert stylists will help you find your perfect outfit!
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Back To Basics Ribbed Knit Midi Dress
Bring your look back to basics with a knit midi dress that can be dressed up or dressed down for whatever mood you're in. The dress features a sleeveless V-neckline, tank-like shoulder straps, and a midi length silhouette. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Tank-like shoulder straps
- Midi length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0932
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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: 05101-001515
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: 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