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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Button Up In Style Midi Dress
Button up in a stylish midi dress! The dress features a sleeveless crew neckline, a midi length silhouette, and a mini side slit with multi-button-up closure. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops.
Fit & Features
- Sleeveless crew neckline
- Mini side slit
- Button-up closure
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1151
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Daydream Floral Mini Dress
You'll look like such a daydream in this adorable floral mini dress. It features a sleeveless V-neckline, bungee spaghetti straps, a mini-length fitted silhouette, and a slightly flared-out hem with a front slit. Complete the look with hoop earrings and strappy sandals.
Fit & Features
- V-neckline
- Bungee spaghetti straps
- Short, fitted silhouette
- Slightly flared-out hem, front slit
- Knit fabric, plenty of stretch
- Ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-4172
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Style Icon Gauze Cutout Maxi Dress
Create a stylish moment with a maxi dress that is perf for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, a high side slit, and a maxi silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Waist cutouts with bar straps
- Maxi silhouette
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1314
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirt Alert Floral Slit Midi Dress
Leg pop approved. With a pleated waist and wrap-front slit, this floral midi dress brings the flirty vibes for any night out or dressed-up moment.
Fit & Features
- Stretch knit fabric with floral print
- Square neckline, spaghetti straps
- Side pleated seam
- Front wrap slit
- Bodycon silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000199
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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For The Thrill Of Knit Mini Dress
Keep it stunning with a mini dress that wows! The dress features a sleeveless scoop neckline, spaghetti straps, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1154
Category Name: Casual Dresses
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally Fab Tie Dye Midi Dress
Keep it totally fab with a midi dress that channels those pretty vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tie-dye print, and a midi silhouette with a high side slit. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-dye print
- Midi silhouette
- High side slit
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1633
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Spotted In Style Leopard Mini Dress
Get spotted in this mini dress that brings the bold factor to your look! The dress features a sleeveless V-neckline, bungee spaghetti straps, a leopard print, a mini side slit, and a mini-length silhouette. The dress is composed of a lightweight knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Leopard print
- Mini side slit
- Mini length silhouette
- Lightweight knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-2138
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take Me Away Tropical Tie-Dye Maxi Dress
Get carried away in this laid-back maxi dress! The dress features a tropical tie-dye print, a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a smocked waist, 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 mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Smocked waist
- Maxi length silhouette, high side slit
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0576
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Mood Ruched Mini Dress
Channel a floral mood in this romantic mini dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a floral print, a ruched drawstring at the side, and a mini-length silhouette. The dress is composed of lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and a clutch.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Floral print
- Ruched drawstring at the side
- Lined mesh fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-1044
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Color Me In Glam Tie Dye Mini Dress
Keep it colorfully glam with a mini dress that is everything! The dress features a sleeveless square neckline, spaghetti straps, a tie-dye hue, a ruched body throughout, and a mini-length silhouette. Complete look with mules and statement cuff.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye hue
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4077
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual-Chic Sweater Knit Dress
Casual and chic, this sweater knit dress is perf for a weekend getaway. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, and a curve-hugging longline silhouette. Style this dress with a floppy hat and cute sunnies.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Cross-back design
- Form-fitting longline silhouette
- Ribbed sweater knit fabric
- Runs true to size
Style Number/Barcode: 06005-1150
Category Name: Casual Dresses
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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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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Feelin' Fierce Leopard Print Mini Dress
You'll be feelin' fierce and fashionable in this trendy leopard print mini dress! It features a strapless sweetheart neckline with a tie-front detail, a cutout under the bust, and a short, form-fitting style to hug your curves. Complete the look with chic mules.
Fit & Features
- Strapless sweetheart neckline
- Tie-front
- Cutout under the bust
- Mini-length, form-hugging fit
- Smocked woven fabric
- Leopard print
- Runs true to size
Style Number/Barcode: 05102-1327
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Trendy In Tie-Dye Satin Mini Dress
Showcase your trendy style this summer season in this adorable satin mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back design, ruched detailing with side ties, a short, curve-hugging silhouette, and a fab all-over tie-dye print. Complete the look with hoop earrings and clear heels.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Cross-back design
- Ruching, side ties
- Mini-length, form-hugging fit
- Satin fabric, tie-dye print, mini skirt length knit lining
- Runs true to size
Style Number/Barcode: 05102-1322
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Palm Ruched Maxi Dress
Keep it pretty underneath the palm trees in a maxi dress that will have you vacay-ready! The dress features a sleeveless square neckline, adjustable spaghetti straps, a pretty tropical palm leaf print, a high ruched side slit, and a maxi length silhouette. 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 square neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- High ruched side slit
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0639
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Pop Ruffled Mini Dress
Add a pop of florals to your look with a mini dress that brings the romance! The dress features an off-the-shoulder neckline, a sweetheart bust with ruffled trim, short sleeves, and a ditsy floral print. The dress is composed of a lined mesh fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Off the shoulder neckline, padded cups
- Sweetheart bust, ruffled trim
- Short sleeves
- Ditsy floral print
- Mini length silhouette
- Lined mesh fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05101-1009
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Electric Strapless Jean Denim Mini Dress
Unlock the power of style in this strapless denim jeans with a jean-like design and bodycon fit that stands out from the crowd!
Fit & Features
- Denim acid wash fabric with stretch
- Strapless neckline, button closure, belt loops
- Front zipper closure
- Jean-like design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6045
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: DENIM, DARK
Available Size: XS, S, M, L
Product Badge:- Sale
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Basic And Trendy Collared Mini Dress
Basic and trendy, this knit mini dress is a summer must-have. It features a sleeveless collared V-neckline, a button-down front, ruched detailing, and a short, curve-hugging silhouette. Style this dress with casual sneakers for the perf everyday look.
Fit & Features
- Sleeveless collared V-neckline
- Button-down front
- Ruching
- Mini-length, form-hugging fit
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4238
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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Totally Fab Tie Dye Ruched Mini Dress
Keep it totally fab with a ruched mini dress! The dress features a sleeveless square neckline, spaghetti straps, tie-dye print, a ruched body, 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
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye print
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4078
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Basic Ruched Midi Dress
Keep it basic with a midi dress that can be dressed up for your next date night! The dress features a sleeveless square neckline, tank-shoulder straps, a ruched high side slit with a drawstring and a midi length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and hoops.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Ruched high side slit
- Drawstring
- Midi length silhouette
- Ribbed knit fabric
- Form hugging, moderate stretch, runs true to size
Style Number/Barcode: 05102-2181
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Basics Sleeveless Midi Dress
Keep it stylish with a midi dress that can be dressed up! The dress features a sleeveless V-neckline, spaghetti straps, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules and a metal cuff.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0947
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale