Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, 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 dinner date, these casual dresses are made to move with your mood—and your calendar.
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Everyday Ease: Casual Dresses for Transitional-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. Layer your favorite long sleeve to keep the chill out, or pick your Windsor shoes and accessories, and you're ready for the day.
Laid-Back & Versatile
Knit, ribbed, crochet, and sweater dresses bring comfort and style to cooler 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 nuetral 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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Absolute Bombshell Cutout Mini Dress
This sultry mini dress will have you looking like an absolute bombshell! It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to a back cutout, and a mini-length, curve-hugging silhouette. Complete the look with hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual waist cutouts that lead to a back cutout
- Short, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4166
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Nights Like This Cutout Mini Dress
Nights like this call for a stunning dress to celebrate with the squad! The dress features a sleeveless sweetheart neckline, waist cutouts, a double row of O-rings, a ruched body, and a mini-length silhouette. Complete look with rhinestone heels and statement earrings.
Fit & Features
- Sleeveless sweetheart neckline
- Waist cutouts
- O-Rings accents
- Ruched body
- Mini-length silhouette, form-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4060
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Second Take Denim Lace-Up Mini Dress
Make them all take a second look at you in this stunning mini dress! The dress features a sleeveless square neckline, a backless design with a lace-up back, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Backless, lace-up straps
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0577
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Island Glam Tropical Maxi Dress
Dazzle with an island-inspired look in this maxi dress that brings those vacay vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tropical floral print, a high side slit, and a maxi length silhouette. Complete look with wedges and a floppy hat.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tropical floral print
- High side slit
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-0318
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic And Captivating Mesh Maxi Dress
Keep it chic and captivating with a mesh dress that wows! The dress features a sleeveless square neckline, adjustable spaghetti straps, a ruched drawstring at the hem, a high side slit, and a mini length lining with a sheer mesh maxi-length hem. Complete look with rhinestone heels.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched drawstring at the hem
- High side slit
- Mini length lining, maxi-length hem
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0594
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunset Stunner Asymmetrical Midi Dress
This dress will have you looking stunning as you watch the sunset on your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a beautiful tropical floral print, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with hoop earrings and strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back cross-back design
- Ruched detailing
- Mid-length, form-hugging fit, asymmetrical hem
- Knit fabric, moderate stretch, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-1860
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Fever Ribbed Knit Mini Dress
Keep it stylish with a floral dress that is all the rage! The dress features a sleeveless sweetheart neckline, spaghetti straps, a tie-front at the bust, a ditsy floral print, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless sweetheart neckline
- Spaghetti straps
- Tie-front
- Ditsy floral print
- Mini-length silhouette
- Ribbed knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2032
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic High-Slit Basic Maxi Dress
Basic yet oh-so-chic, this sleeveless maxi dress will be your new go-to. It features a crew neckline, tank shoulder straps, a sultry thigh-high side slit, and a floor-length fitted silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Thigh-high side slit
- Floor-length fitted silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4090
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Vibes Sleeveless Maxi Dress
Bring on the effortless vibes this season with this pretty maxi dress! It features a sleeveless square neckline, spaghetti straps, side pockets, and a flowy silhouette with an asymmetrical hem. Cinch the dress with a belt and style it with mules for an adorable look.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side pockets
- Flowy, relaxed fit
- Asymmetrical hem
- Smooth knit fabric
- Runs true to size
Style Number/Barcode: 05102-4171
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Jetsetter Tropical Print Maxi Dress
Nail your vacay-bound look with a maxi dress that brings those tropical vibes! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a high side slit, and a tropical palm leaf print. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and sunglasses.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back
- High side slit
- Tropical palm leaf print
- Maxi length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0542
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Boho-Chic Crochet Midi Dress
Bring the boho-chic vibes to your stylish summer look with this stunning midi dress! It features a sleeveless scoop neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a sheer crochet fabric with a trendy fringe hem. Wear this dress as a cover-up over your fave bikini for the perf poolside outfit.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Mid-length, form-hugging fit
- Sheer crochet fabric, fringe hem
- Runs true to size
Style Number/Barcode: 06005-0949
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stunner Ribbed Knit Midi Dress
Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, O-ring accent
- Midi-length
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4071
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Meant To Be Ruffled Mini Dress
You and this dress are totally meant to be! The dress features a sleeveless V-neckline, spaghetti straps, lace-up back, a mini-length silhouette with a faux-wrap overlay, and ruffles. The dress is composed of a mesh fabric that offers a form-hugging fit with a moderate stretch. Complete the look with platform wedges and a butterfly necklace.
Fit & Features
- Sleeveless V-neckline
- Lace-up back
- Mini length silhouette
- Faux-wrap overlay
- Ruffles
- Lined mesh fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0758
Category Name: Casual Dresses
Price: $38.90
Availability: Out of Stock
Product Badge:- Ships Free
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All About Floral Lace Skater Dress
Showcase your love for lace with a skater dress that says it all! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a sheer floral lace back, and a flirty and flowy skater silhouette. Complete the look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, sheer floral lace back
- Hidden side zipper and hook and eye closure
- Skater silhouette
- Lined chiffon fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-0832
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cut It Out Babe Midi Dress
Effortless, but make it extra. With a bold cutout bodice and sleek side slit, this midi dress hugs in all the right places for dates, brunch, or casual plans.
Fit & Features
- Stretchy rib knit fabric, contrast trim
- Square neck, tank shoulder straps
- Cutout bodice
- Side slit
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000045
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All My Love Ditsy Floral Mini Dress
Keep it lovely and gorge with a mini dress that shows off your sweet side! The dress features a ditsy floral print, a sleeveless square neckline, spaghetti straps, a lower back keyhole with tie-back straps, and a skater silhouette with a ruffled hem. Complete look with chunky sneakers.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Lower back keyhole
- Tie-back straps
- Skater silhouette, ruffled hem
- Lightweight woven fabric, ditsy floral print
- Relaxed fit, no stretch
- Runs true to size
Style Number/Barcode: 05102-4147
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Vacay Vibes Crochet Knit Maxi Dress
Channel those vacay vibes with a maxi dress that brings those resort vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, a lower back keyhole with tie-back straps, and a maxi length silhouette. The dress is composed of a lined gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Lower back keyhole with tie-back straps
- Maxi length silhouette
- Lined gauze knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-0297
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Mesmerizing Beauty Puff Sleeve Eyelet Skater Dress
Mesmerize with a skater dress that is perf for your next photoshoot! The dress features a square neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet pattern
- Skater silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4073
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Let Beauty Bloom Floral Midi Dress
Let your beauty bloom with a midi dress that is perf for the season! The dress features a sleeveless cowl neckline, adjustable spaghetti straps that lead to a cross-back, a tropical floral print, ruching, and a midi-length silhouette with an asymmetrical hem. Complete look with wedges.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Cross-back
- Tropical floral print
- Midi length silhouette
- Asymmetrical hem
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0328
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laid Back Glamour Crochet Knit Midi Dress
Keep it effortlessly glam with a crochet-knit dress! The dress features a sleeveless V-neckline, a mini side slit, and a midi length silhouette. The dress is composed of a crochet knit fabric that offers a relaxed fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Mini side slit
- Midi length silhouette
- Crochet knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0674
Category Name: Casual Dresses
Price: $15.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Total Knockout Knit Midi Dress
Step up in this knockout midi dress that is all the rage! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a crew neckline, cap sleeves, and a midi-length silhouette accented with a high side slit. Elevate your look with square toe strappy mules and statement-making earrings!
Fits & Features
- Crew neckline
- Cap sleeves
- Midi length hem
- High side slit
- Ribbed knit fabric
- Plenty of stretch, form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-0897
Category Name: Casual Dresses
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Crew neckline
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Perfect Pick Ditsy Floral Mini Dress
This adorable ditsy floral mini dress is the perfect pick to add to your summer wardrobe! It features a sleeveless square neckline, thin ruffled shoulder straps, ruched detailing with a front drawstring, and a mini-length, curve-hugging silhouette. Style this dress with cute wedges for a weekend brunch.
Fit & Features
- Sleeveless square neckline
- Thin ruffled shoulder straps
- Ruched detailing, front drawstring
- Short, form-hugging fit
- Ribbed knit fabric, ditsy floral print
- Runs true to size
Style Number/Barcode: 05102-2963
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Me Back Tropical Maxi Dress
Get taken back to that dream vacay with a fab maxi dress! The dress features a sleeveless V-neckline, adjustable spaghetti straps that cross at the back, a tropical print, an open back, a smocked waist, and a flowy maxi length silhouette. Complete with wedges.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross at back
- Tropical print
- Open back
- Smocked waist
- Maxi length silhouette
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-0572
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty And Flowy Halter Skater Dress
Showcase your flirty style in this adorable flowy skater dress! It features a sleeveless deep V-neckline, halter straps, dual tie-back accents, a high waist, and a flared-out skater skirt. Complete the look with rhinestone earrings and clear heels.
Fit & Features
- Sleeveless V-neckline
- Halter straps, dual tie-back accents
- High waist
- Flowy skater skirt, fit and flare silhouette
- Chambray fabric
- Runs true to size
Style Number/Barcode: 05102-0488
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale