Casual Dresses
Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, 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 outing, these casual dresses are built to move with your mood—and your calendar.
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STYLE SPOTLIGHT
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Everyday Ease: Casual Dresses for Cool-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.
Laid-Back & Versatile
Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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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Stay Cozy Cable Knit Mini Dress
Keep it cozy with a mini dress that is perf for a casual date night! The dress features a wrap V-neckline, long balloon sleeves with ribbed cuffs, a cinching tie waist with belt loops, and a mini-length silhouette. The dress is composed of cable knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties.
Fit & Features
- Wrap V-neckline
- Long balloon sleeves, ribbed cuffed hems
- Tie-waist belt with belt loops
- Mini-length silhouette
- Cable knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4250
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Sassy Chiffon Mini Dress
Sweet and sassy will be your go-to style in this adorable chiffon mini dress. It features a sweetheart neckline, a tie-front detail at the bust, long sheer bishop sleeves, a stretchy smocked back design, a short, form-hugging silhouette, and an all-over leopard print pattern. Complete the outfit with clear mules and a trendy shoulder bag.
Fit & Features
- Sweetheart neckline
- Tie-front detail at the bust
- Long sheer bishop sleeves, elastic cinched hems
- Stretchy smocked back design
- High waist seam, mini-length, form-fitting silhouette
- Sheer chiffon fabric, knit lining, leopard print
- Runs true to size
Style Number/Barcode: 05101-1267
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Silhouette Long Sleeve Maxi Dress
Create a chic silhouette in this curve-hugging maxi dress. It features a crew neckline, long fitted sleeves, a stylish cutout at the lower back, and a floor-length form-hugging fit with a side slit. Style this dress with clear heels.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Cutout at the lower back
- Floor-length, form-hugging fit
- Side slit
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4137
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keep It Trendy Collared Mini Dress
Keep your everyday fall look trendy and on point with this casual-chic mini dress! It features a collared V-neckline, long fitted sleeves with slit details at the hems, a vertical seam detail running down the center with ruching, and a short, curve-hugging silhouette. Style this dress with knee-high boots.
Fit & Features
- Collared V-neckline
- Long fitted sleeves, slit details at the hems
- Vertical seam detail down the center, ruching
- Mini-length, form-fitting silhouette
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4266
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Glam Button Down Mini Dress
Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Shoulder pads
- Mini length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4265
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Moves Mesh Mini Dress
Make stylish trendy moves in this must-have mesh mini dress. It features a sleeveless square neckline, spaghetti straps, side ruching, and a short, curve-hugging silhouette. The sheer mesh fabric has a full knit lining and showcases an all-over subtle zebra print. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper and hook and eye closure
- Side ruching, mini-length, form-fitting silhouette
- Sheer mesh fabric, full knit lining, moderate stretch
- Zebra print
- Runs true to size
Style Number/Barcode: 05102-4211
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off-The-Shoulder Ribbed Knit Mini Dress
Channel those effortless chic vibes with this sweater mini dress that slays! The dress features an off-the-shoulder neckline, a faux button-down front, long sleeves, 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.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Off-the-shoulder neckline
- Faux button-down front
- Long fitted sleeves
- Lettuce edge hems
- Mini-length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1015
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get A Clue Plaid Blazer Dress
Showcase a trendy look with this effortlessly fab dress that will give you an all-in-one outfit! It features a blazer-designed top with a V-neckline and a lapel collar, shoulder pads, long sleeves, a dual snap-button front, a waist cutout, and a short fitted skirt with a high waist and a faux button-down design. The plaid woven fabric has a smooth lining and no stretch. Pair this dress with strappy mules.
Fit & Features
- Blazer-designed top
- V-neckline, lapel collar
- Shoulder pads, long sleeves
- Dual snap-button front
- Waist cutout, hidden side zipper closure
- Short fitted skirt, high waist, faux button-down design
- Woven fabric, smooth lining, no stretch, plaid print
- Runs true to size
Style Number/Barcode: 05102-4209
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Glam Button Down Mini Dress
Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Shoulder pads
- Mini length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4264
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daring Button Up Midi Dress
Dare to button up in a midi dress that showcases your curves. The dress features a collared neckline, a button-down front, long sleeves, dual waist cutouts, and a midi-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.
Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Dual waist cutouts
- Midi length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4268
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Kiss and Tell Sweetheart Cutout Midi Dress
She’s sweet but knows how to steal the spotlight. This bodycon midi dress brings the heat with a front twist, flirty cutout, and high side slit that does the most (in the best way).
Fit & Features
- Rib knit fabric, sewn-in mesh lining, moderate stretch
- Sweetheart neckline, cutout accent
- Spaghetti straps
- High side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000208
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: GREEN
Available Size: XS, S, M, L
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Bad To The Bone Halloween Mini Dress
Get a bad-to-the-bone spooky look with this mini dress that brings the ghoul factor to your costume! The mini dress features a mock neck, short sleeves, a skeleton graphic, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with over-the-knee boots and adhesive face gems.
Fit & Features
- Mock neck
- Short sleeves
- Skeleton graphic
- Mini length silhouette
- Cotton knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.
Style Number/Barcode: 05102-4247
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cross Out The Drama Bodycon Dress
Cut the drama from your life in a dress that features a halter neck, cross-straps at the bodice, a sexy cutout at the midriff, a bold open back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Halter neck
- Cross-straps at bodice
- Cutout at the midriff
- Open back
- Mini-length silhouette
- Cotton knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4392
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Street Rider Graphic Lace-Up Tee
Show off your need for speed with a graphic tee that gives your look an edgy feel. The tee features a crew neckline, short sleeves, a graphic that reads: " The Street Riders", an image of a skull with a helmet, and a lace-up front. The tee is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots.
Fit & Features
- Crew neckline
- Short sleeves
- Graphic: "The Street Riders"
- Image of a skull with helmet
- Lace-up front
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1024
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hauntingly Stylish Mesh Mini Dress
You'll look hauntingly stylish in this form-hugging mini dress! It features a sleeveless crew neckline, tank shoulder straps, and a mini-length bodycon silhouette. The sheer mesh fabric includes a full lining and showcases an all-over spiderweb print, perf for spooky season! Wear this dress with sleek hoop earrings.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Short, form-hugging silhouette
- Sheer mesh fabric, full knit lining, moderate stretch
- Spiderweb pattern
- Runs true to size
Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.
Style Number/Barcode: 05102-4141
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ride Or Die Baddie Mini Dress
Here's looking at you baddie! Keep it bold in a mini dress that features a sleeveless scoop neckline, tank shoulder straps, a graphic that reads: "Old Motorcycle, Extraordinary Performance", an image of a motorcycle with wings, ruched drawstrings at the hem, 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 a moto jacket and ankle booties.
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Graphic: "Old Motorcycle, Extraordinary Performance"
- Image of a motorcycle with wings
- Ruched drawstrings at hem
- Mini length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
Style Number/Barcode: 06002-0802
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Fave Flowy V-Neck Midi Dress
This breezy lightweight midi dress will be your new casual fave for weekend plans. Designed with a sleeveless V-neck, low back, and mid-length flowy fit, style with a layered necklace and strappy sandals.
Fit & Features
- Gauze woven fabric, mini-length stretchy knit lining
- Sleeveless V-neckline
- Adjustable spaghetti straps, low back
- Hidden side pockets
- High side slit
- Midi-length flowy silhouette
- Runs true to size
Style Number/Barcode: 05102-000185
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Glam Ghoul Skeleton Print Mini Dress
Get a spooky glam look that will have your whole squad jealous in this fab mini dress! It features a sleeveless scoop neckline, spaghetti straps, a front skeleton print, and a short, form-hugging silhouette. Complete your Halloween costume with dazzling face gems and strappy heels.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Front skeleton print
- Mini-length, form-fitting silhouette
- Cotton fabric, moderate stretch
- Runs true to size
Halloween Costumes are considered final sale merchandise. FINAL SALE merchandise may not be returned or exchanged.
Style Number/Barcode: 05102-4149
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Style Plaid Mini Dress
Showcase a chic and perfect style in this plaid mini dress that is a must-have for fall. It features a sleeveless square neckline, spaghetti straps, and a short, curve-hugging fit. Complete the outfit with a faux leather jacket to add an edgy vibe to the look.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-fitting silhouette
- Knit fabric, moderate stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 05102-1864
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Cut Out Mini Dress
Create a perf casual-chic look with this must-have mini dress. It features a sweetheart neckline, long fitted sleeves, an adjustable drawstring at the bust, a sultry waist cutout, ruching, and a short, form-hugging silhouette. Style this dress with sneakers.
Fit & Features
- Sweetheart neckline
- Long fitted sleeves
- Adjustable drawstring at the bust
- Waist cutout, ruching
- Mini-length, form-fitting silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4095
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Fab Sleeveless Plaid Mini Dress
Keep it so fab in a plaid dress that impresses! The dress features a sleeveless square neckline, spaghetti straps, a plaid 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 combat boots and layer with a long sleeve top.
Fit & Features
- Sleeveless square neckline
- Plaid print
- Spaghetti straps
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4231
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Up With Knit Colorblock Mini Dress
Keep up this season in a fab mini dress that is perf to layer on the style! The dress features a crew neckline, long sleeves, a colorblock pattern, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with ankle booties!
Fit & Features
- Crew neckline
- Long sleeves
- Colorblock pattern with exposed seams
- Mini-length silhouette
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4300
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Crazy About Ruche Collared Mini Dress
Keep on trend with a mini dress that shows off your love for ruching! The dress features a collared neckline, a multi-button down front, long sleeves, a ruched body, and a mini-length silhouette. The dress is composed of a slinky knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Collared neckline
- Long sleeves
- Multi-button down front
- Ruched body
- Mini length silhouette
- Slinky knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05101-1314
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bring On Basics Sleeveless Midi Dress
Bring on those basic vibes with a dress that is perf for every day! The dress features a sleeveless V-neckline, tank shoulder straps, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Midi-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4221
Category Name: Casual Dresses
Price: $32.90
Availability: Out of Stock
Product Badge:- Sale