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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Fall In Love Floral Eyelet A-Line Mini Dress
A flirty floral mini dress to attend parties, brunch, and day dates! This sleeveless dress boasts a classy V-neckline and a flattering a-line silhouette on pretty eyelet woven fabric with a dainty floral print. Pair with mules.
Fit & Features
- Dainty floral print
- Eyelet woven fabric lined with stretchy knit
- V-neckline, adjustable spaghetti straps
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6038
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweeter Than Pie Scoop Neck Gingham Mini Dress
So on trend and sweeter than pie, this gingham mini dress is essential for spring-to-summer fun! This mini-length dress is made from woven fabric and features a charming gingham print that exudes effortless style. The scoop neckline and tank shoulder straps flatter your figure, while the form-hugging fit accentuates your curves. Complete the look in cute sandals and a mini purse!
Fit & Features
- Gingham print, woven fabric, slight stretch
- Back zipper closure
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5568
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Days Floral Chiffon Skater Dress
Swing into the sunnier days ahead in this floral chiffon dress! It features a sleeveless square neck, adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffle short-length skater silhouette. Complete the look in cute espadrille wedges for a family picnic!
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Stretchy smocked bodice
- Skater silhouette, tiered ruffles
- Short-length hem
- Floral print, airy chiffon, knit lining
- Runs true to size
Style Number/Barcode: 05102-4936
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Blissful Cutie Floral Bodycon Midi Dress
Enter a state of blissful cuteness in this floral midi dress boasting a flattering bodycon fit perfect for layering with denim jacket.
Fit & Features
- Eyelet knit stretchy fabric, sewn-in knit lining
- Strapless neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6044
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Subtle Charm V-Neck Ruffled Floral Skater Dress
Embrace your inner charm in this floral skater dress at showers or birthdays! The flattering V-neckline and adjustable spaghetti straps provide a perfect fit, while the tiered ruffled skater silhouette adds a touch of feminine flair. With its tie-back design, short-length hem and beautiful floral print, this dress will make you feel effortlessly stylish. Complete the look in mules and earrings!
Fit & Features
- Ditsy floral print
- Chiffon fabric lined with stretchy knit
- Adjustable spaghetti straps
- Tie-back design
- Tiered ruffled skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3022
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Style Leopard And Floral Print Mini Dress
Create a weekend look exuding trendy style with this multi-print mini dress! The stretchy sheer mesh fabric is detailed with a leopard and rose print for a sweet and sassy vibe. The short dress features a sleeveless V-neckline accented with a dainty sheer lace trim, spaghetti straps, and a flowy A-line silhouette with a mini-length hem. Style with cowgirl boots!
Fit & Features
- Leopard and rose-print
- Stretchy sheer mesh fabric with knit lining
- V-neckline with sheer lace trim
- Spaghetti straps
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5764
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Exquisite Charm A-Line Floral Mini Dress
The perfect floral mini dress pick for your weekend plans! Showcasing a flattering sweetheart ruffle neckline and a-line silhouette, this dress will capture your heart. Pair with heels.
Fit & Features
- Ditsy floral print, cotton knit fabric lined
- Strapless sweetheart ruffle neckline
- Padded bra cups
- Back zipper and hook-eye closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6033
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bright Beauty Halter Cutout Tropical Maxi Dress
You'll look bright and beautiful in this tropical maxi dress on vacation or at a weekend pool party! The halter neckline with a spaghetti strap tie highlights your shoulders, while the U-ring insert adds some structure. The cutout back with smocked detail flatters your figure along the flowy maxi-length silhouette. Complete the look with sunglasses and sandals for a chic vibe!
Fit & Features
- Tropical print, chiffon fabric, short stretchy knit lining
- Halter neckline with spaghetti strap tie, U-ring insert
- Cutout back with smocking
- Flowy maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5791
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Unforgettably Bold Abstract Mesh Mini Dress
Bold and unforgettable—this halter mini dress brings the heat with a plunging neckline and layered ruffle skirt in a fiery abstract print.
Fit & Features
- Abstract print, mesh-lined fabric, moderate stretch
- Halter plunge neckline, tie closure
- A-line form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000243
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Fabulous Destination Tropical Cowl Neck Maxi Dress
Look fabulous heading to your destination in this tropical maxi dress for the cutest look on the island or beach resort! The cowl neckline creates a flattering drape and spaghetti strap tie while the low cowl back adds a touch of allure. The flowy maxi silhouette will make you feel like you're on a tropical escape! Complete the look in sunnies.
Fit & Features
- Tropical palm print, stretchy knit fabric
- Cowl neckline
- Low cowl back, spaghetti strap tie
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5727
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Note To Self Ribbed Knit A-Line Mini Dress
Note to self, this sleeveless mini dress is a must-have for every day! Perfect for any occasion, this stretchy ribbed knit dress will surely become a staple in your wardrobe. It features a crew neckline with tank straps and a flattering A-line silhouette with a flirty front slit on the mini-length hem. Complete the look with an oversized blazer and a sleek necklace.
Fit & Features
- Soft and stretchy ribbed knit fabric
- Crew neckline
- Tank shoulder straps
- Front slit
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5632
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cutest Look Ditsy Floral Ruched Knit Mini Dress
Create the cutest look for your weekend plans in this floral ruched knit mini dress! The adorable ditsy floral print on the soft and stretchy brushed knit fabric will give your casual look a flirtatious vibe! The short dress features a sleeveless square neckline with tie-shoulder spaghetti straps for a trendy detail and customized fit. The ruching down the side seams will show off your curves on the bodycon silhouette. Style this dress with hoop earrings and strappy mules for brunch with your girls!
Fit & Features
- Ditsy floral print
- Stretchy brushed knit fabric
- Sleeveless square neckline
- Tie-shoulder spaghetti straps
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5533
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Striking Impression Sleeveless Slit Mesh Maxi Dress
Impress with your striking style in this sleeveless mesh maxi dress perfect for dressy occasions! This dress will show off your curves with a square neckline, adjustable spaghetti straps, and a form-hugging fit. The sheer slit maxi-length hem adds a touch of elegance and allure. Complete the look with strappy stiletto heels.
Fit & Features
- Sheer mesh fabric, partial knit lining
- Square neckline
- Adjustable spaghetti straps
- Form-hugging fit
- Sheer slit mesh maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5583
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Ditsy Floral V-Neck Mini Dress
This ditsy floral mini dress will have you dreaming of sunshine days! Flaunt your figure with the bodycon fit of this dress showcasing a flattering V-neckline, dainty spaghetti straps, a tie-front bust for added detail, and a mini-length hem on ditsy floral print mesh fabric. Complete the look in sandals and a mini tote bag.
Fit & Features
- Ditsy floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Slit accent
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5571
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Days Square Neck Tie-Back Skater Short Dress
Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!
Fit & Features
- Lightweight cotton fabric with woven lining
- Stretchy smocked bodice
- Tie-back waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5417
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Impressive Blossom Strapless Floral Maxi Dress
Impress in this floral maxi dress showcasing a sleek strapless neckline and a column silhouette that flatters your figure. Style the dress with a choker.
Fit & Features
- Statement floral print
- Mesh fabric lined with soft, stretch knit
- Column silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5953
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's Stylish Mock Neck Cable Knit Midi Dress
A stylish sleeveless midi dress featuring a mock neck, a flattering form-hugging fit, and a side slit for movement. Complete the look with strappy heels.
Fit & Features
- Cable knit fabric, stretchy knit lining
- Mock neck
- Side slit
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5897
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Cute In Plaid Strapless Plaid A-Line Mini Dress
Look and feel cute in this plaid strapless dress with a flattering A-line silhouette and a mini-length hem. Complete the look with a choker necklace.
Fit & Features
- Plaid print, woven fabric, woven lining
- Strapless neckline
- Back zipper closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5980
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Currently In Paradise V-Neck Tropical Midi Dress
This tropical midi dress will be with you paradise for a stylishly chic vacation! Featuring a V-neckline adorned with spaghetti straps and a tie-back design, it's the perfect form-hugging dress for any island adventure. With a side slit and midi-length hem, you'll be sure to turn heads! Complete the look in wedge sandals and earrings.
Fit & Features
- Tropical print, stretchy knit fabric, sewn-in knit lining
- Spaghetti straps
- V-Neckline
- Tie-back design
- Side slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5633
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Ways V-Neck Floral Crepe A-Line Dress
All eyes and hearts will be on you in this floral crepe mini dress all season! With puff sleeves and a mini-length hem, this dress is perfect for a playful day out. The A-line silhouette will flatter your figure, making you stand out in style. Complete the look in wedge sandals.
Fit & Features
- Floral print, crepe fabric, moderate stretch
- V-neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5700
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fabulous Icon Sleeveless Ribbed Knit Midi Dress
An iconic knit midi dress that can go from day to night! Crafted from soft and stretchy ribbed knit fabric, this sleeveless dress offers a stylish square neckline, a flattering underbust seam, and a bodycon silhouette that will hug your curves in all the right places. Complete the look with a moto jacket and stiletto heels for a chic style.
Fit & Features
- Soft, stretchy ribbed knit fabric
- Square neckline
- Underbust seam
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-1853
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fun In Floral Lace Mini Dress
So fun in floral print, this lace dress is featured in a form-hugging A-line silhouette and playful mini-length hem. Pair with cute wedge sandals for a cute summer look!
Fit & Features
- Floral print, lace fabric, stretchy knit lining
- Square neck with bust tie
- Adjustable spaghetti straps
- Form-hugging A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6015
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Charmer Basic Rib Knit Maxi Dress
A basic maxi dress that brings everyday charm! This long rib knit dress features a square neckline, spaghetti straps, and a flattering bodycon silhouette, you'll love this maxi dress for any occasion. Complete the look in a cute crop jacket and your favorite sneakers!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5522
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cherry On Top Lace-Up Cutout Chiffon Skater Dress
Nothing says wow like this chiffon skater dress that puts the cherry on top of your look at brunch, birthdays, or shower celebrations! Designed with a V-neckline, adjustable ruffled straps, and a pleated bust, this dress accentuates your curves. The cutout waist and back with lace-up detailing add a playful touch, while the skater silhouette and tiered ruffled hem give a flirty and flattering fit! Complete the look in fashionable platform sneakers.
Fit & Features
- Chiffon fabric lined with woven fabric
- Adjustable ruffled straps
- Lace-up, back zipper hook-eye closure
- Cut out sides and back
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2947
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale