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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Look So Sweet Floral Applique Skater Party Dress
Effortlessly steal the show in this skater party dress at graduations or showers! Made with organza sheer fabric and adorned with delicate floral applique, this dress is sure to turn heads and make you feel like the belle of the ball. Designed with a flattering square neckline and adjustable spaghetti straps, the skater silhouette and short-length hem exude flirty charm so everyone will fall for you! Complete the look in strappy platform heels.
Fit & Features
- Floral appliques
- Sheer organza fabric with woven lining
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3084
Category Name: Casual Dresses
Price: $56.90
Availability: Out of Stock
Product Badge:- Sale
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True Devotion Strapless Ruffle Skater Mini Dress
Express your true devotion to flirty style in this strapless skater dress perfect for strolling a beach city or a brunch! Featuring a flattering strapless neckline with a tie and stretchy elasticized bands for a comfortable, secure fit. The skater silhouette and ruffled mini-length hem add a touch of flirty fun. Complete the look in strappy sandals.
Fit & Features
- Cotton woven fabric with non-stretch lining
- Strapless neckline with tie
- Skater silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-5711
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Upgrading V-Neck Lace Up Bodycon Mini Dress
Upgrade your style with this sleeveless mini dress for weekend plans! The sleek V-neckline and spaghetti straps accentuate your feminine figure, while the front lace-up and slit add a touch of allure to the mini-length hem. Complete the look with a sleek layered necklace.
Fit & Features
- Stretchy ribbed knit fabric
- Spaghetti straps
- V-neckline
- Lace-up front and slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2004
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Slay Halter Cowl Neck Ribbed Knit Maxi Dress
This sleek halter cowl neck maxi dress is a simple chic style that will make your casual outfits slay! Made with a lightweight stretchy ribbed knit fabric, it features a sleeveless draped cowl neckline with tie-back halter spaghetti straps, an alluring open back with a lower tie-back strap, and a form-hugging maxi-length silhouette to flaunt your stunning figure. Pair with slip-on sandals for a relaxing weekend getaway.
Fit & Features
- Stretchy ribbed knit fabric, partial front knit lining
- Cowl neckline, halter spaghetti straps
- Open back, tie-back strap
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5685
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Strolls In The Sand V-Neck Tropical Skater Mini Dress
Getaway in this tropical skater mini dress to the beach or on vacay! Featuring adjustable spaghetti straps and a flattering V-neckline, this dress hugs your silhouette with an elasticized waist and side cutouts. Its skater silhouette and mini-length hem make it perfect for any daytime adventure. Complete the look in cute sandals.
Fit & Features
- Tropical print, woven fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline
- Elasticized waist with side cutouts
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5656
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wildflower Hour Lace A-Line Mini Dress
Flirty meets sultry in one perfect dress. With a draped cowl neck and delicate floral lace, this A-line mini dress hugs every curve, serving up major after-dark romance.
Fit & Features
- Floral print, lace fabric lined with stretch knit
- Cowl neckline, padded bra cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000477
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Oh So Sweet Tie Back A-Line Mini Dress
You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Square neckline
- Tie back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5682
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set To Amaze Mock Neck Abstract Mini Dress
Everyone will admire your amazing self in this abstract mini dress all over town! Made with a unique abstract print on airy lined mesh fabric, this dress is sure to turn heads. The sleeveless design and mock neckline add a chic touch, while the ruched side seams, bodycon fit, and mini-length hem show off your curves. Complete the look with earrings.
Fit & Features
- Abstract print
- Sheer mesh fabric with knit lining, plenty of stretch
- Mock neckline
- Ruching
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5783
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Miami Nights Sleeveless Tropical Slit Maxi Dress
Turn up the heat in Miami in this tropical maxi dress on vacay! The square neckline and spaghetti straps accentuate your curves in a form-hugging fit while the high side slit adds a touch of sassy sophistication. Let the tropical print and maxi-length hem transport you to a paradise getaway! Complete the look in sandals.
Fit & Features
- Tropical print, knit fabric, stretchy short lining
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5624
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Darling Appeal Sleeveless Ruffled Midi Dress
You'll always give off a darling appeal in this sleeveless midi dress for casual occasions! With a classic square neckline and dual spaghetti straps, this dress is perfect for any occasion. The stretchy smocked bodice ensures a comfortable fit while the A-line silhouette and ruffled midi-length hem add a flattering touch. Complete the look in sandals and a crossbody bag.
Fit & Features
- Woven fabric, no stretch
- Square neckline
- Dual spaghetti straps
- Stretchy smocked bodice
- A-Line ruffled silhouette
- Runs true to size
Style Number/Barcode: 05102-5457
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Walk On The Wild Side Leopard Mesh Mini Dress
Walk on the wild side in this leopard mesh mini dress perfect for brunch or dates! This daring dress features a flattering square neckline, delicate spaghetti straps, and a surplice bodice for a flattering look. The side ruched seams accentuate your curves, giving you a bodycon fit that will make you stand out in any crowd. And with its mini-length hem and fierce leopard print, this dress is perfect for a night out on the town. Complete the look in platform block heels and earrings!
Fit & Features
- Leopard print, stretchy mesh fabric, sewn-in knit lining
- Spaghetti straps
- Side ruched seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5696
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Flawless Crew Neck Textured Midi Dress
Getting ready is a breeze with this casual crew neck midi dress for an effortlessly flawless vibe! Featuring classic cap sleeves and a flattering crew neck, this bodycon dress will hug your curves in all the right places down to the alluring midi-length hem on textured mesh fabric. Complete the look in platform sneakers.
Fit & Features
- Textured sheer mesh fabric
- Stretchy slip lining with adjustable spaghetti straps
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5625
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fit To Bloom Scoop Neck Ditsy Floral Midi Dress
Sweet summer events are calling and this ditsy floral midi dress is here to make you look cute! Adjustable spaghetti straps and a drawstring scoop neckline provide versatile style, while the form-hugging fit and side slit add a touch of sass. Complete the look in high heels.
Fit & Features
- Ditsy floral print, bust lining, knit fabric, moderate stretch
- Spaghetti straps
- Drawstring adjustable scoop neckline, bust tie
- Form-hugging fit
- Side slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5774
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Occasion Strapless Denim Mini Dress
Impress with your OOTD in this strapless denim mini dress to channel iconic moments! The strapless neckline flaunts some skin, the flattering bodycon fit with flexible boning hugs your curves, and the mini-length hem adds a touch of playfulness. Complete the look in chic pointed-toe boots and a purse!
Fit & Features
- Denim fabric, stretchy knit lining
- Strapless neckline
- Back zipper and hook-eye closure
- Flexible boning
- Bodycon fit
- Style runs large
Style Number/Barcode: 05102-5484
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set For Cuteness Twist Back Slit Rib Knit Maxi Dress
You and this maxi dress are set for cuteness all season long! Made with rib knit fabric, this dress is both comfortable and stylish, perfect for any occasion. Featuring a square neckline and shoulder straps, this dress offers a form-hugging fit that will accentuate your curves. The twist-back design adds a trendy touch while the high side slit and maxi-length hem provide an alluring appeal. Complete the look with sandals and sunnies!
Fit & Features
- Stretchy rib knit fabric
- Square neckline
- Shoulder straps
- Twist back design
- High side slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5577
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Blis Sleeveless Bodycon Knit Midi Dress
Sit back and watch the compliments roll in when you're seen in this knit midi dress over the weekend! Crafted from a unique knit fabric offering a stretchy knit lining for comfort. It features adjustable spaghetti straps, a square neckline with a flirty bust tie, and a flattering bodycon midi-length silhouette. Complete the look in strappy sandals and a purse.
Fit & Features
- Unique knit fabric, stretchy knit lining
- Adjustable spaghetti straps
- Square neckline, bust tie
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5712
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Loving Halter Strappy Floral Mini Dress
You'll love this floral mini dress all summer for brunch, picnics, and casual parties! Featuring a halter V-neckline with spaghetti strap ties, an open back with spaghetti strap ties, this bodycon dress is perfect for a fun and flirty look. Style this dress with trendy flat sandals.
Fit & Features
- Floral print, knit fabric with stretchy knit lining
- Halter V-neckline with spaghetti strap ties
- Open back with spaghetti strap ties
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5807
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweeten Up Strappy Back Floral Chiffon Skater Dress
Sweeten up any moment in this floral chiffon skater dress perfect for celebrations and showers! With a square neckline, spaghetti straps, and a playful strappy back design, this dress is perfect for any occasion. The skater silhouette and ruffled short-length hem add a flirty touch, while the ditsy floral print and chiffon fabric keep it light and whimsical. Complete the look in wedges.
Fit & Features
- Ditsy floral print, chiffon fabric lined with stretchy knit
- Spagehtti straps, square neckline
- Strappy back design
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5450
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In A Daze Strapless Cutout Striped Knit Mini Dress
The perfect striped mini dress for summer dazes and effortless styling! Crafted from a stretchy ribbed knit fabric with a trendy striped print, this dress features a strapless straight-across neckline and cutout design at the waist for an alluring vibe. The bodycon fit on the mini-length silhouette will accentuate your gorgeous curves. Style this dress with sunglasses and sandals!
Fit & Features
- Striped pattern
- Stretchy ribbed knit fabric
- Strapless straight neckline
- Waist cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1971
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Times Bodycon Abstract Print Mini Dress
A mini dress that calls for good times only at casual parties or weekend plans! Designed with an alluring abstract print on mesh fabric, this dress is both chic and versatile. The sleeveless crew neckline and bodycon silhouette highlight your curves, while the side ruched seams flatter your figure. Complete the look with a mini shoulder bag and heels.
Fit & Features
- Abstract print
- Mesh fabric, sewn-in knit lining, stretchy
- Side ruched seams
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5606
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Painted Muse Tube Slit Maxi Dress
Like wearing a work of art, this strapless maxi dress stuns with a marbled print and a curve-hugging silhouette. The sleek side slit adds just the right touch of drama for gallery nights, rooftop hotel bars, or dinner downtown.
Fit & Features
- Marbled print stretchy mesh fabric, sewn-in lining
- Tube strapless neckline
- High side slit
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000247
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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On The Prowl V-Neck Leopard A-Line Mini Dress
This leopard mini dress calls for a night on the prowl for the best cocktail! Boast a fierce-sultry vibe in this sleeveless dress featuring a flattering V-neckline, adjustable spaghetti straps for the perfect fit, and an A-line silhouette that gracefully shows off your curves along the mini-length hem. Complete the look in an edgy faux leather jacket.
Fit & Features
- Leopard print, mesh fabric line with stretchy knit
- Adjustable spaghetti straps
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5615
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Beauty Printed Slit Midi Dress
Embrace your inner beauty in this abstract printed slit midi dress for any casual occasion! Featuring a flattering sleeveless square neckline perfect for layering, delicate spaghetti straps, and a bodycon fit, this dress flatters every figure. The front slit and midi-length hem add a touch of elegance, while the abstract print and mesh fabric create a unique style. Complete the look in mules and a cropped jacket.
Fit & Features
- Abstract print, stretchy mesh fabric, sewn-in knit lining
- Spaghetti straps
- Bodycon fit
- Front slit
- Runs true to size
Style Number/Barcode: 05102-5736
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vibrant Strapless Butterfly Print Mini Dress
Set hearts aflutter in this vibrant butterfly print mini dress at parties or concerts! This dress is designed with a retro butterfly print on mesh fabric and boasts a strapless neckline and flattering bodycon fit. The short ruffled hem has a satin bow for added charm to your look! Style with platform shoes.
Fit & Features
- Butterfly print, mesh fabric lined with stretchy knit
- Bodycon fit
- Ruffled mini-length hem with satin bow
- Runs short, size up if desired
Style Number/Barcode: 05102-5775
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale