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
Discover New Skater Dress Styles
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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Perfectly Seasoned Plaid Crew Neck Mini Dress
Fabulous and flavor-filled, step into this plaid mini dress for the new season! The mini dress features fitted long sleeves, a classic crew neckline, and a flattering bodycon silhouette on stretchy knit fabric with a trendy plaid print. Complete the look in a moto jacket for a coffee shop hang!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5247
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Allure Long Sleeve Slit Midi Dress
Your new go-to for looking polished without even trying. This hacci rib knit midi dress serves up a body-skimming fit, cozy texture, and a side slit for just the right amount of edge. Perfect for everything from PSL runs to dinners downtown.
Fit & Features
- Soft hacci rib knit stretch fabric
- Sweetheart neckline
- Fitted long sleeves
- Side slit accent
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000301
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L, XL
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Fine Arts Abstract Mesh Midi Dress
A perfect blend of art and fashion, this mesh midi dress is sure to make everyone's heart race! Feel like a masterpiece in this midi-length dress featuring adjustable spaghetti straps, a V-neckline, a flattering bodycon silhouette, and a center back slit, crafted on abstract print mesh fabric with a knit lining. Complete the look in lace-up heels.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Bodycon silhouette, center back slit
- Midi-length hem
- Abstract print, mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5341
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Timeless Classic Cable Knit A-Line Dress
Bring beauty and charm in this short dress! The mini dress features a V-neckline, long sleeves with flared cuffs, a short-length hem, and a flattering a-line silhouette on lightweight cable knit fabric. Complete the look with a ring set and boots for a casual occasion!
Fit & Features
- Long sleeves, flared cuffs
- V-neckline
- A-line silhouette
- Short-length hem
- Lightweight cable knit fabric
- Runs true to size
Style Number/Barcode: 05102-5355
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Can I Have Your Attention Belted Mini Dress
Capture all the attention in this alluring belted mini dress that will draw in all the compliments! It features a strapless straight-across neckline, front hook and eye closures at the bodice, a high waist seam with a belted design to cinch your silhouette, vertical seams running down the front and back, and a mini-length hem with a bodycon fit. The lined woven fabric has a minimal stretch. Style this edgy-chic dress with hoop earrings and ankle booties!
Fit & Features
- Strapless straight-across neckline
- Front hook and eye closures at the bodice
- High waist seam, belted waist, double grommet design
- Vertical seams down the front and back, back zipper, hook and eye closure
- Mini-length hem, bodycon silhouette
- Woven fabric, full-length knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5382
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Winter Chic Mock Neck Long Sleeve Skater Dress
This chic short skater dress will elevate your casual winter looks! It features a mock neckline, long fitted sleeves, a high waist, a short-length hem, and an adorable fit and flare skater silhouette. The ribbed knit fabric offers plenty of stretch. Style this short dress with over-the-knee boots and hoop earrings for a coffee date!
Fit & Features
- Mock neckline
- Long fitted sleeves
- High waist seam
- Short-length hem
- Skater silhouette
- Lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5445
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Always Stylish And Classic Plaid Mini Dress
This stylish mini dress features a classic plaid print and a bodycon silhouette in soft knit fabric. Its square neckline, spaghetti straps, and mini-length hem make it perfect for a trendy, dressy look for layering. Style with a chic moto jacket and boots for an evening out!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Plaid print, knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5411
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Hottie Cutout Ruched Midi Dress
This curve-hugging cutout midi dress will show off your major hottie status! The mid-length dress features an off-the-shoulder straight-across neckline, long fitted sleeves, alluring front and back waist cutouts, ruching down the side seams, and a bodycon silhouette to flaunt your figure. The lined knit fabric offers plenty of stretch. Style this midi dress with layered chain necklaces and clear strap heels for a rooftop bar.
Fit & Features
- Off-the-shoulder straight-across neckline, elasticized hem
- Long fitted sleeves
- Front and back waist cutouts
- Ruched side seams
- Midi-length hem, bodycon silhouette
- Knit fabric, sewn-in knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5366
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stroll Along Surplice Tie Waist Mini Dress
Stroll along the city streets in this casual mini dress perfect for a day out! The mini dress features relaxed long sleeves with banded cuffs, a V-neckline with a surplice accent, a tie-waist belt, and a flattering bodycon fit on stretchy knit fabric. Complete the look with a crossbody bag.
Fit & Features
- Relaxed long sleeves, banded cuffs
- V-neckline, surplice accent
- Tie-waist belt
- Bodycon fit
- Mini-length hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5354
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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It's A Must Collared Denim Mini Dress
This denim mini dress is a must for curating a cute and trendy lineup this season! The short dress features long sleeves, a collar neckline, zipper front closure, dual flap pockets with snap-button closures and lower pockets, an elasticized waist with belt loop accents, a bodycon fit, and a mini-length hem. Complete the look in pointed-toe booties for a day out with friends!
Fit & Features
- Long sleeves, collar neckline
- Zipper front closure
- Flap pockets with snap-button closures
- Lower pockets
- Bodycon fit, mini-length hem
- Rigid denim fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-5364
Category Name: Casual Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Sale
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Make A Debut Plaid Strapless Pleated Mini Dress
Make a debut in classic plaid and on-trend silhouette! This plaid mini dress is sure to stand out from any crowd. Featuring a strapless neckline, form-hugging bodice, belt loop accents, and a flirty pleated mini-length hem. Complete the look in lug boots for an edgy vibe!
Fit & Features
- Strapless neckline
- Back zipper closure
- Form-hugging bodice
- Belt loop accents
- Pleated mini-length hem
- Plaid print, woven fabric, knit lining at the bust, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5415
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Preppy Posh Strapless A-Line Pleated Mini Dress
Look fabulously mod with this strapless mini dress! Made from smooth woven fabric, discover a next-level fashionista vibe in this dress featuring an A-line silhouette, belt loop accents along the waist, and a pleated mini-length hem for added flair. Complete the look in a blazer for weekend plans!
Fit & Features
- Strapless neckline
- A-line silhouette
- Belt loop accents along the waist
- Pleated mini-length hem
- Smooth woven fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5444
Category Name: Casual Dresses
Price: $6.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Impress Me Pinstripe Strapless Mini Dress
This pinstripe mini dress is sure to impress! Featuring a strapless foldover neckline with non-slip grip lining, a stretchy smocked back, form-hugging silhouette, and a flirty front slit along the hem. Complete the look in a cropped blazer for a posh vibe!
Fit & Features
- Strapless foldover neckline
- Non-slip grip lining
- Stretchy smocked back
- Form-hugging silhouette, front slit, mini-length hem
- Back zipper and hook-eye closure
- Pinstripe print, woven fabric, and lining
- Runs true to size
Style Number/Barcode: 05102-5469
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Must Have Strapless Twist Midi Dress
This midi dress is a must-have style for showing off your shoulder for a brunch or party! It features a strapless sweetheart neckline, a padded and twisted bust, a flattering bodycon silhouette, and a center-back slit on stretchy knit fabric. Complete the look with a chic crossbody bag and heels.
Fit & Features
- Strapless sweetheart neckline, non-slip grip lining
- Padded and twisted bust
- Bodycon silhouette
- Center back slit
- Midi-length hem
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5374
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Girl Energy Houndstooth Knit Mini Dress
Bring the chic girl energy to your fall wardrobe with this trendy mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, and a bodycon silhouette to showcase your curves. The knit fabric features an all-over houndstooth pattern for an elevated vibe. Style this mini dress with a faux leather moto jacket and combat boots!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length hem
- Bodycon silhouette
- Houndstooth pattern
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5410
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Soft Curves Ahead Cap Sleeve Maxi Dress
It’s giving sleek, sculpted, and effortlessly romantic. With a knotted bust, cap sleeves, and a chic back slit, this maxi is your low-key way to steal the spotlight at brunch, cocktail receptions, or date night!
Fit & Features
- Slinky knit fabric, soft knit stretchy lining
- Cap sleeves
- Sweetheart knotted neckline
- Form-hugging silhouette
- Center back slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000268
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Another Day Long Sleeve Sweater Midi Dress
Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Soft, stretchy sweater rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5305
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out For A Ride Denim Moto Belted Mini Dress
This moto denim mini dress brings edgy perfection for your next ride downtown! It features a sleeveless lapel collar neckline, a front exposed zipper closure, a flattering bodycon silhouette, and a belted waist with belt loop accents and buckle closure. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless lapel collar neckline
- Front exposed zipper closure
- Bodycon silhouette
- Belted waist, belt loop accents, buckle closure
- Mini-length hem
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5307
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check It Out Gingham Plaid Mini Dress
Make a statement in this gingham plaid mini dress! The square neckline and spaghetti straps make it the perfect dress for flaunting your curves, while the bodycon silhouette and mini-length hem radiate confidence. Complete the look by layering a long sleeve top for a preppy vibe!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Gingham plaid print
- Texture knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5243
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Things Cute Cable Knit Sweater Dress
Wrap yourself up in this cute and casual cable knit sweater dress perfect for pumpkin patches or festivals! It features long sleeves with banded cuffs, a plunge surplice V-neckline and V-cut back, a tie-waist belt, and a short form-hugging fit. Complete the look in trendy knee-high boots.
Fit & Features
- Long sleeves, banded cuffs
- Plunge surplice V-neckline, V-cut back
- Tie-waist belt
- Form-hugging fit
- Short-length hem
- Cable knit design, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5370
Category Name: Casual Dresses
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic In The City Turtleneck Mini Dress
You'll look chic as you take a stroll in the city in this trendy turtleneck mini dress! It features a turtleneck that you can fold over, long fitted sleeves, ruching down the side seams, a mini-length hem, and a bodycon silhouette to showcase your curves. The soft brushed knit fabric offers plenty of stretch for comfortable wear. Style this mini dress with a faux leather blazer and over-the-knee boots for a cute fall 'fit.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Ruched side seams
- Mini-length hem
- Bodycon silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5220
Category Name: Casual Dresses
Price: $17.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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See Through Me X-Ray Graphic Maxi Dress
See through the ordinary and showcase your unique style! This graphic maxi dress features a scoop neckline, adjustable spaghetti straps, an X-ray graphic bust and front design, a flattering bodycon silhouette, and a back slit on smooth knit fabric. Complete the look in a sassy crop denim jacket for day or night plans!
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps,
- Back zipper and hook-eye closure
- X-ray graphic bust and front design
- Bodycon silhouette, maxi-length hem, back slit
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5297
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Long Sleeve Bodycon Maxi Dress
The perfect maxi dress for looking sultry on casual outings! The long dress features fitted long sleeves, a square neckline, a flattering bodycon silhouette, and a fitted maxI-length hem on smooth modal knit fabric with a mesh lining. Complete the look with simple hoop earrings and a choker.
Fit & Features
- Fitted long sleeves
- Square neckline
- Bodycon silhouette
- Maxi-length hem
- Smooth modal knit fabric, mesh lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5339
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The 90s Are Calling Denim Strapless Mini Dress
This denim mini dress celebrates the fashion of the 90s! The short dress creates a timeless classic look with its strapless neckline, button closure, belt loop accents, and skirt seam detailing to make a bold statement and flattering bodycon silhouette. Complete the look with on-trend chunky platform heels for a party!
Fit & Features
- Strapless neckline
- Button closure, side zipper, belt loop accents
- Skirt seam detailing
- Bodycon silhouette
- Mini-length hem
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5442
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free