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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Paint The Night Abstract Open Back Midi Dress
It’s giving art, elegance, and effortless wow. This slinky slip dress was made to glide through gallery nights, rooftop drinks, and every “who is she?” moment in between.
Fit & Features
- Abstract print, woven fabric
- V-neckline
- Spaghetti straps
- Open strappy back
- Curve-hugging silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-000615
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Perfect Vacation Long Sleeve V-Neck Cutout Mini Dress
This V-neck mini dress pairs perfectly with your next vacation or pool party! This playful and stylish dress features long sleeves with flare cuffs, a V-neckline with a hoop insert, and cutout details on the bodice and back. Its bodycon fit and mini-length hem will highlight your curves while you explore exotic destinations or the resort bar! Complete the look with sunnies.
Fit & Features
- Texture knit fabric, sewn-in knit lining, minimal stretch
- V-Neckline with hoop insert
- Cutout bodice and back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5705
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Buckled Beauty Off-The-Shoulder Knit Mini Dress
An off-the-shoulder mini dress perfect for everyday slays. It features long sleeves and a foldover neckline with trendy buckled accents and a bodycon silhouette. Complete the look with boots.
Fit & Features
- Stretchy rib knit fabric
- Off-the-shoulder neckline, folded with buckled accents
- Long sleeves
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5992
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 Charm Off-The-Shoulder Floral Mesh Mini Dress
Showcase your sweet charm at spring and summer parties in this floral mesh mini dress! The airy sheer mesh fabric is accented with a dainty floral print for the prettiest vibe and includes a full-length knit lining for coverage. The off-the-shoulder sweetheart neckline gives the dress a feminine touch, and features sheer short-sleeved cuffs and a V-cut bust design with a tie-front detail. The ruching down the side seams will accentuate your gorgeous curves along the bodycon silhouette. Style this adorable mini dress with clear heels.
Fit & Features
- Stretchy sheer mesh fabric with knit lining
- Floral print
- Off-the-shoulder sweetheart neckline, short sleeve cuffs
- V-cut bust design with tie-front detail
- Ruched bust and side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-3050
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artsy Babe Paisley Bodycon Slit Midi Dress
Strut like an artsy babe in this paisley mesh midi dress showcasing a flattering bodycon silhouette with a flirty front slit. Complete the look with a handbag.
Fit & Features
- Paisley print, mesh fabric, stretchy knit lining
- Square neckline
- Spaghetti straps
- Bodycon silhouette
- Front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5932
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Day Ruffled Ditsy Floral Skater Dress
You'll love every moment spent in this ditsy floral skater dress! The square neckline and spaghetti tie straps add a flirty touch, while the stretchy smocked bodice ensures a comfortable fit. With a playful ruffled skater silhouette and a mini-length hem, this dress is perfect for any occasion. Complete the look in wedges.
Fit & Features
- Ditsy floral print, woven fabric lined with knit
- Spaghetti tie strap
- Square neckline
- Ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5425
Category Name: Casual Dresses
Price: $20.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorable Looks Tie Front Bodycon Midi Dress
All of your adorable looks this season will include this eyelet midi dress with a flirty tie front and bodycon silhouette. This dress is perfect for shower celebrations or graduations!
Fit & Features
- Eyelet fabric
- Tie front sweetheart neckline
- Spaghetti straps
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6008
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Breeze Tropical Cutout Slit Maxi Dress
Feel the island breeze in this tropical maxi dress while on vacation! With a square neckline, spaghetti straps, and a form-hugging fit, this maxi dress is perfect for a day in the sun. The cutout bodice and high front slit add a touch of playfulness to your island look. Complete the look with sandals.
Fit & Features
- Tropical palm print, smooth stretchy knit fabric, sewn-in knit lining
- Square neckline
- Spaghetti straps
- Cutout bodice, high slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5670
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Breezes Halter Boho Satin Maxi Dress
Enter the room in this chic boho satin maxi dress to make a bold impression! The sleeveless dress boasts a halter neckline and a flowy silhouette adorned with a high front slit. Style with stiletto heels.
Fit & Features
- Boho print, satin woven fabric. sewn-in woven lining
- Halter neckline
- Spaghetti strap
- Flowy silhouette
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5865
Category Name: Casual Dresses
Price: $12.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty Picture Striped Midi Dress
With an ice cream in hand and strappy sandals on, this striped midi dress will have you looking pretty everywhere you go! Featuring a flattering square neck and curve-hugging fit, this dress accentuates your figure down to the midi hem.
Fit & Features
- Striped print, stretchy knit fabric, sewn-in knit lining
- Square neckline
- Wide shoulder straps
- Curve-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5860
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Lovely Floral Eyelet Mini Dress
Oh-so-lovely, this floral eyelet knit mini dress is perfect for weekend brunch. You'll adore the short puff sleeves, sweet tie-front detail, and pretty A-line silhouette.
Fit & Features
- Sheer eyelet knit fabric with knit lining, plenty of stretch
- Dainty floral print
- Sweetheart neckline, ruched bust
- Keyhole cutout, tie-front detail
- Short puff sleeves, elastic cinched hems
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6050
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Preppy Edit Pinstripe Mini Dress
The perfect dress for fall—this strapless pinstripe mini dress blends polished structure with playful pleats. Toss on a blazer or knee-high boots for seasonal chic.
Fit & Features
- Pinstripe pattern, woven fabric
- Strapless collared neckline
- Button front
- Fitted bodice
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5993
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: GRAY
Available Size: XS, S, M, L
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Alluring Silhouette Off-The-Shoulder Maxi Dress
Show off your alluring curves in this off-the-shoulder maxi dress crafted from a rib knit fabric that fits like a glove!
Fit & Features
- Rib knit stretchy fabric
- Off-the-shoulder neckline
- Twisted strap details
- Bodycon silhouette
- Flared maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6020
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Talker Strappy Back Halter Skater Mini Dress
Sweeten any room with your vibe in this halter skater dress, which flaunts a strappy open back that turns heads with every wear!
Fit & Features
- Woven fabric, stretchy knit lining
- Halter V-neckline with spaghetti strap tie
- Open back with tie-back detail
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6029
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Cutesy V-Neck Gingham Skater Dress
Get cutesy in this gingham skater dress for a dreamy look this spring to summer! With a lace trim neckline and flattering drop waist seam that accentuates your figure, this short dress looks like a dream.
Fit & Features
- Gingham print, poplin woven fabric, lined
- Laced trim V-neckline
- Spaghetti straps
- Button front details
- Drop waist seam
- Skater silhouette, short-length hem
- Runs true to size
Style Number/Barcode: 05102-5990
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Just For Fun Strapless Floral A-Line Mini Dress
A floral mini dress made for fun and compliments! With a flattering strapless neckline and A-line silhouette, you'll look and feel your best.
Fit & Features
- Floral print, eyelet fabric lined with stretchy knit
- Strapless neckline
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6040
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plaid Mood Sleeveless A-Line Mini Dress
The plaid mesh mini dress features a sleeveless sweetheart neckline, adjustable spaghetti straps, and an A-line silhouette. Complete the look with loafers for a preppy vibe.
Fit & Features
- Sheer mesh fabric with knit lining, plenty of stretch
- Plaid print
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5987
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Bliss Tie-Back Slit Maxi Dress
Ideal for making a statement at any occasion, this artsy print maxi dress combines chic with effortless style. Featuring a flattering A-line silhouette and a stylish front slit, this dress offers a breezy look that turns heads with a tie-back design.
Fit & Features
- Artsy print, woven fabric, stretchy knit lining
- V-neckline
- Adjustable spaghetti straps
- Tie-back design
- A-line silhouette
- Front slit, flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6039
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutest Spirit Short Sleeve Knot Tie Mini Dress
This short sleeve mini dress is the cutest for casual outings! Made from soft and stretchy rib knit fabric, this dress will keep you comfy and stylish all day long. With a flattering bodycon fit and a unique front knot tie detail, this dress exudes charm. The asymmetrical mini-length hem adds a touch of playfulness, making this a must-have. Complete the look in platform sneakers.
Fit & Features
- Rib knit fabric, moderate stretch
- Crew neckline
- Bodycon fit
- Front knot tie detail
- Runs true to size
Style Number/Barcode: 05102-5762
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreamy Look Abstract Print Mesh Midi Dress
Create a dreamy look to catch all the stares in this abstract print mesh midi dress designed with a high front slit on a curve-hugging bodycon silhouette.
Fit & Features
- Sheer mesh fabric with full-length brushed knit lining, high stretch
- Abstract print
- Sleeveless square neck and back
- Spaghetti straps
- Midi-length hem, high front slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5876
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Street Chic Faux Suede Mini Dress
A little jacket inspo, a lot of city attitude. This faux suede mini dress brings structure and edge to your fall lineup. Perfect for styling with a long sleeve top and boots on crisp autumn days.
Fit & Features
- Soft, smooth faux suede fabric
- Mock neckline, dual snap-button closures
- Front zip-up closure
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000202
Category Name: Casual Dresses
Price: $59.90
Availability: In Stock
Available Color: TAUPE
Available Size: S, M, L
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Easy And Breezy Lace-Up Midi Dress With Pockets
So effortlessly breezy for any plans, this A-line midi dress will turn heads with a lace-up bust and back detail, while the hidden side pockets are perfect for stashing your phone or lip gloss in.
Fit & Features
- Poplin woven fabric, woven lining
- Sweetheart neckline, lace-up front, stretchy smocked bust
- Spaghetti straps
- Lace-up back, lower zipper and hook-eye closure
- Drop waist seam, hidden side pockets
- A-line silhouette, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6023
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Many Admirers Open Back Bodycon Midi Dress
Crafted in a smooth knit fabric that hugs every curve, this cap sleeve midi dress will leave your admirers speechless! The dress boasts a showstopping open back while the bodycon silhouette flaunts your figure along the slit midi-length hem. Pair with stiletto heels.
Fit & Features
- Smooth knit stretchy fabric
- Cap sleeves
- Scoop neckline
- Open back
- Bodycon silhouette
- Midi-length hem, side slit
- Runs true to size
Style Number/Barcode: 05102-5984
Category Name: Casual Dresses
Price: $14.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Charm Crew Neck Bodycon Midi Dress
The perfect basic midi dress for any occasion! It features a classic crew neck, cap sleeves, and a bodycon silhouette that flatters your curves. Pair with sleek heels and earrings.
Fit & Features
- Smooth jersey knit fabric, double-lined
- Crew neck
- Cap sleeves
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5661
Category Name: Casual Dresses
Price: $28.90
Availability: Out of Stock
Product Badge:- Sale