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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Sweet As Honey Strapless Floral Skater Dress
Look and feel oh-so-sweet in this strapless floral skater dress with a flirty ruffled hem perfect for day dates or parties!
Fit & Features
- Floral print, woven fabric, stretchy knit lining
- Strapless neckline
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-3881
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Ruched Snake Print Mini Dress
You'll look so sultry and stylish in this trendy snake print mini dress. It features a V neckline, long fitted sleeves, front ruched detailing, and a short, curve-hugging fit. Pair this dress with sleek gold hoop earrings and a chic clutch for a night out.
Fit & Features
- V neckline
- Long fitted sleeves
- Front ruched detailing
- Mini length
- Form-hugging fit
- Snake print
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-1073
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Real Ruched Mini Dress
Keep it real in this dress that keeps it chic! The dress features a mock neck, long sleeves, ruched side seams, and a mini length silhouette. The dress is composed of knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sleek mules.
Fit & Features
- Mock neck
- Long sleeves
- Ruched side seams
- Mini length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0870
Category Name: Casual Dresses
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Chic Mini Dress
Style up this trendy mini dress for a casually chic look! It features tank-like shoulder straps, a scoop neckline, and a short, curve-hugging fit. Pair this ribbed knit dress with the matching jacket and chunky sneakers for the perf everyday 'fit.
Shop Matching Jacket: Casually Chic Cropped Jacket
Fit & Features
- Tank-like shoulder straps
- Scoop neckline
- Short, form-hugging fit
- Ribbed knit fabric
- Moderate stretch
Style Number/Barcode: 05102-1061
Category Name: Casual Dresses
Price: $19.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Easily Stunning Strapless Cutout Striped Mini Dress
Take a stroll looking stunning in this striped mini dress with a sexy cutout and bodycon silhouette to flaunt your figure!
Fit & Features
- Striped print, stretchy knit fabric
- Strapless sweetheart neckline
- Button accents, cutout bodice
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2233
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Good Vibes Word Screen Ruched Dress
Showcase those good vibes in this trendy ruched dress! It features tank-like shoulder straps, a round neckline, side ties, and can be worn as a mini or midi dress. The knit fabric has an all-over word screen print for a cool look. Pair this dress with chunky sneakers to keep it casual or strappy heels for an elevated 'fit.
Fit & Features
- Tank-like shoulder straps
- Round neckline
- Ruched detailing
- Side ties at the hem
- Word screen print
- Knit fabric with plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1071
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Mood Ribbed Knit Maxi Dress
We're in the mood for basics! Slay in this dress that keeps it effortlessly chic. The dress features a trendy turtle neck, long sleeves, and a maxi length silhouette with a high center back slit. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with sneakers to nail those low-key vibes.
Fit & Features
- Turtle neck
- Long sleeves
- Maxi length silhouette
- High center back slit
- Ribbed knit fabric
- Plenty of stretch
- Form-hugging fit
Style Number/Barcode: 05102-1117
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Must-Have Ribbed Knit Mini Dress
This must-have ribbed knit mini dress needs to be in your closet this season! It features a mock neckline, long fitted sleeves, a short, form-hugging fit, and a cute merrow edge trim. Pair this dress with chunky sneakers for a casual 'fit to hang with the squad.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini length silhouette
- Curve-hugging fit
- Ribbed knit fabric with plenty of stretch
- Merrow edge trim
Style Number/Barcode: 05102-0928
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cozy Knit Long Sleeve Tunic
You'll be so cozy and chic in this adorable knit tunic! It features a ribbed crew neckline, long sleeves with ribbed hems, a low V back with a strap detail, side slits, and a relaxed and comfortable fit. Pair this tunic with leggings and ankle booties or wear it as a dress with thigh-high boots.
Fit & Features
- Ribbed crew neckline
- Long sleeves with ribbed hems
- Low V back with strap detail
- Side slits
- Relaxed fit
- Knit fabric with minimal stretch
Style Number/Barcode: 06005-0716
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off the Shoulder Long Sleeve Mini Dress
Stun in a basic off the shoulder dress that keeps it casual and cute. The dress features an off the shoulder neckline, long ruched sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with plenty of stretch. Complete the look with clear mules.
Fit & Features
- Off the shoulder neckline
- Long ruched sleeves
- Mini length silhouette
- Knit fabric
- Form-hugging fit
- Plenty of stretch
Style Number/Barcode: 05102-0937
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortlessly Chic Sleeveless Mini Dress
You'll look so effortlessly chic in this simple yet stylish mini dress! It features a sleeveless bodice, a high neckline, and a mini length, curve-hugging silhouette. The knit fabric is lined and offers plenty of stretch for comfortable wear. Pair this dress with a denim jacket for a casual look or a blazer for an elevated vibe.
Fit & Features
- High neckline
- Short, form-hugging fit
- Lined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0994
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sporty-Chic Long Sleeve Mini Dress
Give your everyday look a sporty-chic vibe by styling up this adorable mini dress! It features long fitted sleeves, a mock neckline with a partial zip front, and a short, form-hugging fit. Pair this dress with chunky sneakers to casually slay your 'fit!
Fit & Features
- Long fitted sleeves
- Mock neckline
- Partial zip front
- Mini length
- Curve-hugging silhouette
- Double-lined brushed knit fabric
- Plenty of stetch
Style Number/Barcode: 05102-0930
Category Name: Casual Dresses
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Basic Midi Dress
Bring it back to basics in a ribbed dress that showcases your curves in all the right places. The dress features a scoop neckline, long sleeves, 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 look with ankle booties.
Fit & Features
- Scoop neckline
- Long sleeves
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0800
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slay In Basics Ribbed Knit Mini Dress
Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Mock neck
- Long sleeves
- Rounded mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0852
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keepin' Knit Cute Ruched Mini Dress
Keep your 'fit cute and stylish in this knit mini dress! It features a crew neckline, long fitted sleeves, a high waist seam, front ruched detailing with dual adjustable drawstrings at the hem, and a short, curve-hugging silhouette. Pair this dress with chunky sneaks for a casual feel, or dress it up with heels and a layered necklace.
Fit & Features
- Crew neckline
- Long fitted sleeves
- High waist seam
- Front ruched detailing
- Dual adjustable drawstrings at the hem
- Short, form-hugging fit
- Brushed knit fabric with plenty of stretch
Style Number/Barcode: 05102-1047
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep Knit Cozy Mini Sweater Dress
Keep your look cozy and chic in this mini sweater knit dress! It features a trendy mock neckline, long fitted sleeves, and a short, curve-hugging silhouette. Pair this dress with thigh-high boots for an adorable date night 'fit.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Front seam detailing
- Short, form-hugging fit
- Sweater knit fabric with moderate stretch
Style Number/Barcode: 06005-0717
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Casual Hoodie Mini Dress
Keep it casual in a mini dress that is part cozy and part glam. The hoodie mini dress features a corset bodice with piping detail, long sleeves, a hoodie, and a mini length silhouette. The mini dress is composed of a knit fabric that offers a form hugging fit. Complete look with chunky sneakers.
Fit & Features
- Corset-like bodice with piping seams
- Hoodie
- Long sleeves with ribbed cuff
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 06002-0670
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Play On Sleeveless Plaid Mini Dress
Keep it playful and poised in a dress that is totally on-trend, babe! The dress features a sleeveless scoop neckline, a plaid print, and a mini length silhouette. The dress is composed of a brushed knit fabric. Complete look with ankle booties.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Plaid print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1067
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Knit Cute and Casual Ribbed Midi Dress
Keep it cute and casual in a knit dress that is perfect for a quick coffee run or a casual date with bae. The dress features a scoop neckline, long sleeves, a midi length silhouette, and composed of a ribbed brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers.
Fit & Features
- Scoop neckline
- Long sleeves
- Midi length silhouette
- Ribbed
- Brushed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1042
Category Name: Casual Dresses
Price: $15.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Flair Striped Knit Off-The-Shoulder Mini Dress
Showcase a cozy flair in this mini dress made with striped ribbed knit fabric offering plenty of stretch for comfortable wear. It features an off-the-shoulder neckline with a fold-over design, long fitted sleeves, and a short A-line silhouette for an adorable vibe.
Fit & Features
- Striped ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5883
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Basic Ribbed Knit Mini Dress
Rock a basic mini dress for that next coffee date with bae or layer up for a casual shopping spree. The dress features a notched V-neckline, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit that offers a moderate stretch. Complete look with ankle booties.
Fit & Features
- Notched V-neckline
- Long sleeves
- Mini length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-1060
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Crush Cozy Mini Dress
You'll absolutely love this cozy crush-worthy mini dress! It features an off the shoulder fold-over neckline, long blouson sleeves with tapered hems, and a mini length, curve-hugging silhouette. The lightweight knit fabric has a cashmere-like feel and offers plenty of stretch. Pair this dress with thigh-high boots for the perf holiday look.
Fit & Features
- Off the shoulder fold-over neckline
- Long blouson sleeves
- Short, form-hugging fit
- Soft knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0970
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Babe Off The Shoulder Sweater Dress
Showcase your major babe status in this chic sweater dress! It features an off the shoulder neckline with a fold-over detail, long fitted sleeves, and a mini length, curve-hugging silhouette. Pair this dress with thigh-high boots for an adorable date night look.
Fit & Features
- Off the shoulder neckline
- Fold-over detail
- Long fitted sleeves
- Short, form-hugging fit
- Angora knit fabric
- Plenty of stretch
Style Number/Barcode: 06005-0811
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylish Babe Scoop Neck Mini Dress
You'll be a total stylish babe in this chic mini dress! It features a wide scoop neckline, long fitted sleeves, and a curve-hugging, mini length silhouette. The dress is composed of a brushed knit fabric with plenty of stretch for comfortable wear. Pair this dress with thigh-high boots to elevate it to a night out look!
Fit & Features
- Wide scoop neckline
- Long fitted sleeves
- Short, form-hugging fit
- Brushed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0986
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance