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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Gorgeous One Shoulder Bodycon Mini Dress
Look like a gorgeous dream in this sleeveless mini dress for showers, brunch, or parties! The one shoulder neckline adds a chic look, while the side ruched seams enhance your curves. The bodycon fit hugs your figure in all the right places along the mini-length hem. Complete the look with statement earrings.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- One shoulder neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3478
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever Sweet Long Sleeve Drop Waist Skater Dress
Stay forever sweet in this skater dress featuring a sleek square neckline and ruching that flatters your figure. Pair with heels.
Fit & Features
- Stretchy smooth knit fabric
- Square neckline
- Long fitted sleeves
- Ruching
- Drop waist
- Mini-length tiered skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3745
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Showstopper Abstract Print Mesh Maxi Dress
Serve chic vibes in this airy-lined mesh maxi dress designed with a multi-colored abstract print for a bold allure. It features a strapless straight-across neckline, a high-cut side slit, and a long bodycon silhouette to showcase your stunning curves.
Fit & Features
- Abstract printed sheer mesh fabric with knit lining, plenty of stretch
- Strapless straight neckline
- High side slit
- Maxi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5982
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Vibes Tropical Print Asymmetric Midi Dress
Channel those island vibes on your summer vacay in this tropical print asymmetric midi dress! The stretchy slinky knit fabric is accented with an abstract tropical pattern, an iconic look for your getaway. The mid-length dress features a sleeveless cowl neckline with chic draped detailing, tie-back halter straps, an alluring open back, an asymmetric high-cut hem, and a bodycon silhouette to hug your gorgeous curves. Style with sleek hoops for a sunset happy hour.
Fit & Features
- Abstract tropical print
- Stretchy knit fabric, knit bust lining
- Cowl neckline, tie-back halter straps
- Open back
- Asymmetric hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5810
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Babe Drop Waist Bubble Hem Skater Dress
You'll be a total flirty babe in this adorable short dress featuring a sleeveless square neckline with spaghetti straps, a V-shaped drop waist design, and a pleated skater silhouette with the cutest bubble hem. Style with hoop earrings and mules for date night!
Fit & Features
- Ribbed knit bodice, poplin woven skirt with knit lining, moderate stretch
- Square neckline
- Spaghetti straps
- V-shaped drop waist
- Short pleated skater silhouette with bubble hem
- Runs true to size
Style Number/Barcode: 05102-5907
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sheer Exellence Mock Neck Bodycon Mesh Midi Dress
Experience sheer excellence in this stunning mesh midi dress perfect for dinners downtown or concerts. The sheer short sleeves and mock neckline add a touch of chic, while the bodycon silhouette flatters your figure. The sheer mesh fabric and smooth knit slip provide a luxurious feel, and adjustable spaghetti straps ensure a perfect fit. Complete the look with this midi dress in block heels and a hair clip for a fashion-forward style!
Fit & Features
- Sheer mesh fabric
- Includes a smooth knit slip, adjustable spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5540
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Weekend Feeling Sleeveless Bubble Hem Mini Dress
A sleeveless knit dress features a classic crew neckline, a form-hugging fit, and a trending drop waist seam with a bubble mini-length hem. Style with a denim jacket for casual plans.
Fit & Features
- Knit fabric, moderate stretch
- Crew neckline
- Form-hugging fit
- Drop waist seam, bubble mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5873
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Awaken Beauty A-Line Lace Short Dress
Transform into a vision of beauty in this lace short dress at every party! This stunning dress boasts a sleeveless square neckline with a tie, enhancing your feminine charm. The A-line silhouette and short-length hem flatter your figure, while the intricate lace fabric adds a touch of elegance. Complete the look in stiletto mules and a purse!
Fit & Features
- Lace fabric lined with stretchy knit
- Square neckline with tie
- Wide shoulder straps
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5552
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute In The City V-Neck Knit Midi Dress
You'll be looking cute in the city in this casual midi dress perfect for a dinner date! It features bell long sleeves, a front and back V-neckline, and a flattering bodycon silhouette on rib knit fabric with a sewn-in knit lining. Complete the look with a chic crossbody bag.
Fit & Features
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Bell long sleeves
- Front and back V-neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5192
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flouncin' Around Strapless Ruffle Mini Dress
Show off your fun and flirty side in this strapless mini dress at parties and on dates! Featuring a figure-hugging bodycon fit, side ruched seams, and a playful ruffled mini-length hem, this dress is perfect for any occasion. Complete the look with block heels.
Fit & Features
- Double-lined smooth knit stretchy fabric
- Strapless neckline
- Bodycon fit
- Ruffled
- Runs true to size
Style Number/Barcode: 05102-5771
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Of Details V-Neck Lace-Up Skater Dress
Fall in love with every chic detail of this lace skater dress sure to romance every room you walk into! With adjustable spaghetti straps and a flattering V-neckline, our dress features a lace-up mesh bodice and a playful skater silhouette. The asymmetrical ruffled trim adds a touch of flirty sophistication, making it the perfect for brides, birthday girls, or party guests! Complete the look with dainty earrings and heels.
Fit & Features
- Lace fabric line with stretchy knit
- Adjustable spaghetti straps, V-neckline
- Back zipper and hook-eye closure
- Mesh lace-up bodice
- Asymmetrical ruffles
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3436
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swoon Over You Strapless Lace Mini Dress
This stunning strapless lace mini dress will make everyone swoon over your beauty at summer parties! Crafted with an airy sheer lace fabric with a knit lining for coverage, this mini-length dress is the charming style you need for the season. It features a strapless straight-across neckline with a dainty trim, a ruched seam to accentuate your curves leading to an adjustable drawstring and side slit, a ruffled hem for a flirty vibe, and a bodycon fit to flaunt your figure. Complete your look with hoop earrings and espadrille sandals.
Fit & Features
- Sheer lace fabric with knit lining, moderate stretch
- Strapless straight neckline
- Ruched seam, adjustable drawstring
- Side slit
- Ruffled hem
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3405
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chicest Vibe Drop Waist Bubble Hem Mini Dress
This chic sleeveless mini dress brings flirtiness to the party or dressy dinner out! The dress boasts a trendy drop waist seam leading to the pleated bubble mini-length hem. Complete the look heels or knee-high boots.
Fit & Features
- Ribbed knit and woven fabrics, moderate stretch
- Mock neckline
- Tank shoulder straps
- Drop waist
- Mini-length pleated bubble hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5861
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Delightful View Collared Scenic Waist Skater Dress
You'll be such a delightful view in this collared skater dress strolling the streets of Silicy or downtown! Featuring long sleeves with buttoned cuffs and a collared V-neckline, hidden front hook and eye fasteners provide a seamless look, and a scenic printed waist and short skater silhouette add a touch of charm. Complete the look in heels and a crossbody purse.
Fit & Features
- Gauze woven fabric with lining, no stretch
- Collared V-neckline
- Hidden front hook and eye fasteners
- Scenic printed waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5638
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Marble Sleeveless Mesh Midi Dress
A sleeveless abstract marble print mesh midi dress features a sleek crew neckline, a flattering form-hugging fit, and a flirty side slit. Pair with heels.
Fit & Features
- Abstract marble printed sheer mesh fabric with brushed knit lining, plenty of stretch
- Sleeveless crew neckline
- Tank shoulder straps
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5869
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fall Flair Plaid Woven Bubble Hem Skater Dress
Add some flair to your fall 'fits in this chic skater dress designed with a plaid printed cotton woven fabric. It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, a trendy V-shaped waist, and a short skater silhouette with the cutest bubble hem.
Fit & Features
- Plaid cotton woven fabric with knit lining, minimal stretch
- Square neckline
- Adjustable spaghetti straps
- Back zipper with hook-eye closure
- V-shaped waist
- Short skater silhouette, bubble hem
- Runs true to size
Style Number/Barcode: 05102-5870
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Vibe Halter Drop Waist Skater Dress
Bring a cute vibe to brunch or a party in this halter skater dress showcasing a deep V-neckline and a pleated silhouette for flirty flare. Pair with earrings.
Fit & Features
- Poplin woven fabric with knit lining, minimal stretch
- Deep V-neckline, dart seams at bust
- Tie-back halter straps, partially open back, lower back zipper with hook-eye closure
- V-shaped drop waist
- Pleated short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3516
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ocean Breeze Cowl Neck Low Back Tropical Maxi Dress
Relax poolside with a drink in hand and this tropical mesh maxi dress on! Featuring a playful cowl neckline, adjustable spaghetti straps, and a low back with criss-cross straps for a touch of intrigue. Its curve-hugging silhouette and maxi-length hem will make you feel like a tropical goddess on vacation! Complete the look in sunnies and sandals!
Fit & Features
- Tropical palm print, mesh fabric lined with stretchy knit
- Cowl neckline
- Adjustable spaghetti straps
- Low back with criss-cross straps
- Curve-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5645
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Impression Crew Neck Tie-Dye Bodycon Mini Dress
This tie-dye mini dress will have you falling head over heels! It features classic short sleeves and a crew neckline, a bodycon fit to flaunt your curves, and a mini-length hem. Complete the look with earrings and stiletto heels for any occasion!
Fit & Features
- Tie-dye print, mesh fabric, partial lining
- Crew neckline
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5646
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fresh Lines Sleeveless Pinstripe Mini Tube Dress
Look fresh this season in this strapless pinstripe mini dress boasting a sleek bodycon silhouette and faux front pockets. Pair with chic flats.
Fit & Features
- Woven knit fabrication
- Sleeveless square neckline
- Pinstripe pattern
- Faux front pockets
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-5963
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Chic Icon Long Sleeve Knit Midi Dress
Become an instant chic icon in this bodycon midi dress adorned with flare cuff long sleeves with flirty tie accents and a V-neckline. Pair with mules.
Fit & Features
- Lined brushed knit fabric, plenty of stretch
- V-neckline
- Long fitted sleeves with ruched slit flare accents, adjustable drawstrings
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5895
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dainty-Chic Lace-Trim Woven Corset Skater Dress
This adorable lace-trim woven corset skater dress will bring a dainty-chic style to your party look. The sheer stretch woven fabric offers an airy, lightweight feel with a knit lining for coverage. The short dress features a square neckline with a scalloped lace trim and sheer lace cap sleeves for the prettiest detail. The ruched bust leads to a corset front with a lace-up design for a snatched look. The high waist flows out to a skater skirt with a fit and flare silhouette. Complete your outfit with rhinestone heels for that pop of sparkle.
Fit & Features
- Sheer stretch woven fabric with knit lining
- Square neckline with scalloped lace trim
- Sheer scalloped lace cap sleeves
- Ruched bust, corset bodice with lace-up front
- Back zipper, hook and eye closure
- High waist seam, skater skirt with fit and flare silhouette
- Runs true to size
Style Number/Barcode: 05101-3026
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Life's A Picnic Sweetheart Lace Gingham Mini Dress
Life's a picnic when you look oh-so-cute in this gingham mini dress at summer carnivals and day dates! The adjustable spaghetti straps provide a perfect fit while the lace trim sweetheart neckline adds adorable vibes. The high waist seam and slim fit create a flattering silhouette, while the lace trim mini-length hem adds a playful touch. Complete the look in platform sneakers.
Fit & Features
- Gingham print, cotton woven fabric, no stretch
- Adjustable spaghetti straps
- Lace trim sweetheart neckline
- Lace trim high waist seam
- Slim fit
- Lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5781
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Lady Tie-Dye Cutout Dress
Channel a certain pop culture character from everyone's favorite movie! Go as a Pretty Lady this Halloween wearing this iconic mini dress featuring a sleeveless scoop neck, tank-style straps, a cutout bodice with an o-ring insert, and a tie-dye skirt. Complete your costume with chic thigh-high boots and hoop earrings.
Fit & Features
- Sleeveless scoop neck
- Tank-style straps
- Cutout bodice, o-ring insert
- Tie-dye mini skirt
- Bodycon silhouette
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4745
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale