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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Knit Girl Turtleneck Mini Dress
You'll be a major it girl in this adorable ribbed knit mini dress! It features a cozy turtleneck, long fitted sleeves, and a mini length, curve-hugging silhouette. This dress is perf for a holiday party, styled with thigh-high boots for a chic look.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Short, form-hugging fit
- Ribbed knit fabric
- Moderate stretch
Style Number/Barcode: 05102-0589
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfect Look In Plaid Knit Mini Dress
Get a perfect look in this adorable plaid knit mini dress! It features a sleeveless bodice with spaghetti straps, a scoop neckline, and a short, curve-hugging fit. Pair this cute and casual dress with chunky sneakers and layer on a denim jacket.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- Plaid print
- Lightweight unlined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-1066
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Slay Ribbed Knit Mini Dress
Casually slay your everyday 'fit in this adorable ribbed knit mini dress! It features tank-like shoulder straps, a notch front V neckline, and a short, curve-hugging fit. Pair this dress with chunky sneakers and gold hoop earrings.
Fit & Features
- Tank-like shoulder straps
- Notch front V neckline
- Mini length silhouette
- Form-hugging fit
- Lined ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-1057
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Vibes Tie Dye Mini Dress
Get major trendy vibes in this must-have tie dye mini dress. It features long fitted sleeves, a short, curve-hugging silhouette, and has flattering ruched detailing with side ties at the hem. The dress is composed of a lightweight knit fabric with plenty of stretch. Complete your look with chunky sneakers and gold hoop earrings.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Ruched detailing
- Side ties at hem
- Stretchy knit fabric
- Tie dye print
Style Number/Barcode: 05102-1070
Category Name: Casual Dresses
Price: $14.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feelin' Trendy Tie Dye Mini Dress
Get an effortless and trendy look in this tie dye mini dress! It features long fitted sleeves, slashed detailing on the left side of the bodice and the right side by the bottom hem, and a neutral all-over tie dye print. Pair this dress with chunky sneakers and hoop earrings for a casual look to hang with the squad.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Slashed detailing
- Tie dye print
- Soft knit fabric
- Plenty of stretch
Style Number/Barcode: 06002-0680
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keeping Knit Casual Ribbed Mini Dress
Keep it cute and casual in a wrap mini dress that is perfect for dinner with the squad. The dress features an off the shoulder neckline, long Dolman sleeves, a bar strap accent at the back, a cinching tie waist belt, 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 ankle booties.
Fit & Features
- Off the shoulder neckline
- Bar strap at the back
- Long Dolman sleeves
- Tie waist belt with belt loops
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 06005-0804
Category Name: Casual Dresses
Price: $24.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sultry Style Snake Print Mini Dress
You'll definitely have that sultry style in this trendy snake print mini dress! It features spaghetti straps, a scoop neckline, and a short, curve-hugging silhouette. Pair this dress with a faux leather jacket for a girl's night out.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- All-over snake print
- Knit fabric with moderate stretch
Style Number/Barcode: 05102-1069
Category Name: Casual Dresses
Price: $19.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy And Cute Cable Knit Mini Dress
Get a cozy and cute look this season in this adorable cable knit mini dress! It features a wrap front and back design with a deep V-neckline, long loose sleeves with tapered hems, a tie-front waist, and a short, curve-hugging fit. Pair this dress with thigh-high boots for a date night.
Fit & Features
- Wrap front and back
- V-neckline
- Long sleeves
- Tie-front waist
- Mini-length silhouette, form-hugging fit
- Cable knit fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1003
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Sweetheart Ribbed Knit Midi Dress
Showcase the stylish sweetheart you are in this trendy ribbed knit midi dress! It features a sweetheart neckline with bust seam detailing, a mid-calf length and a curve-hugging silhouette. The ribbed knit fabric offers plenty of stretch for comfortable wear. Pair this dress with heeled booties and layer on a faux leather jacket for an edgy vibe.
Fit & Features
- Spaghetti straps
- Sweetheart neckline
- Bust seam detailing
- Mid-length, form-hugging fit
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-1040
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Babe Ribbed Knit Mini Dress
Being basic isn't a bad thing babe! Style up this essential ribbed knit mini dress for a cute everyday look. It features a mock neckline, long fitted sleeves, and a short, curve-hugging silhouette. The ribbed knit fabric has a soft, cashmere-like feel and offers plenty of stretch. Pair this dress with chunky sneakers for a casual vibe.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini length silhouette
- Form-hugging fit
- Brushed ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0947
Category Name: Casual Dresses
Price: $10.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Adorable Look Plaid Print Strapless Skater Dress
Adorably chic will be your vibe in this woven skater dress designed with a classic plaid print. It features a strapless subtle sweetheart neckline, a drop waist, and a short pleated skater silhouette for that cute flair.
Fit & Features
- Plaid printed woven fabric
- Strapless sweetheart neckline
- Back zipper closure
- Drop waist
- Mini-length pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5925
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Slay Square Neck Ruched Mini Dress
Casually slay in this adorable ruched dress! It features bungee spaghetti straps, a trendy square neckline, ruched side detailing, and a mini length, form-hugging silhouette to enhance your curves. Pair this dress with thigh-high boots for a majorly chic look.
Fit & Features
- Bungee spaghetti straps
- Square neckline
- Ruched side detailing
- Mini length silhouette
- Form-hugging fit
- Rayon fabric with plenty of stretch
Style Number/Barcode: 05102-1030
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Every Day Ribbed Knit Midi Dress
This knit dress is perfect for your everyday occasions! Layer with chunky sneakers and dainty rings to create a chic back to school outfit this season. The dress features a mock neck, long sleeves, a midi-length silhouette, and composed of a soft to the touch ribbed knit fabric that enhances curves.
Fit & Features
- Mock neck
- Long sleeves
- Midi length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0960
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Side Slit Ribbed Knit Mini Dress
Amp up your basic mini dress with a trendy side slit! This staple piece dress features a mock neck, long sleeves, and a side slit. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Mock neck
- Long sleeves
- Side slit
- Mini length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0966
Category Name: Casual Dresses
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Houndstooth Scoop Neck Mini Dress
Stay on-trend in a mini dress that slays this season. The dress features a sleeveless scoop neckline, sleek spaghetti straps, a houndstooth print, and a mini length silhouette. Complete your look with a faux fur jacket.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Houndstooth print
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 05102-1036
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Babe Alert Snake Print Mini Dress
Babe alert! You'll be looking majorly chic in this trendy mini dress! It features a mock neckline, long fitted sleeves with thumb holes, ruched detailing, and a short, curve-hugging silhouette. The dress is composed of a stretchy lightweight knit fabric with an allover snake print that would pair perfectly with chunky sneakers. Wear this dress to hang with the squad!
Fit & Features
- Mock neckline
- Long fitted sleeves with thumb holes
- Ruched detailing
- Short, form-hugging fit
- Stretchy lightweight knit fabric
- Allover snake print
Style Number/Barcode: 05102-1012
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Vibes Button Down Ribbed Mini Dress
Rock a basic mini dress to layer with your favorite denim jacket or moto jacket this season. The dress features a crew neckline, a button-down front, long sleeves, and a mini length silhouette with a raw edge hem. The dress is composed of a ribbed knit fabric.
Fit & Features
- Crew neckline
- Button-down front
- Long sleeves
- Mini length silhouette, raw edge hem
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0955
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Corset Cutie Denim Mini Dress
From brunch dates to fun at the fair, she always eats. This skater denim mini dress serves flirty and fierce with a corset bodice and sweet bust tie that gives major retro babe energy.
Fit & Features
- Denim fabric, lace trim woven lining
- Corset-style bodice with lace paneling, flexible boning
- Sweetheart neckline, bust tie, lace trim, underwire bust
- Adjustable lace trim shoulder straps
- Back lace-up detail, zipper and hook-eye closure
- Drop waist skater skirt with lace trim, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000157
Category Name: Casual Dresses
Price: $9.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleeveless Shaggy Knit Mini Dress
Keep it chic in a shaggy knit dress that brings flair to your wardrobe. The dress features a sleeveless scoop neckline, tank straps, and a mini length silhouette. The dress is composed of an unlined shaggy knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless scoop neckline
- Tank straps
- Mini length silhouette
- Shaggy knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0982
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Brushed Knit Sleeveless Crew Neck Midi Dress
Slip into this adorable sleeveless midi dress for a chic everyday look! It features a crew neckline and a mid-calf length, curve-hugging silhouette. The brushed knit fabric has a soft cashmere-like feel. Pair this dress with chunky sneakers for a casual vibe or heeled booties for a date night.
Fit & Features
- Crew neckline
- Tank-like shoulder straps
- Mid-length, form-hugging fit
- Brushed knit fabric
Style Number/Barcode: 05102-0984
Category Name: Casual Dresses
Price: $15.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keep It Chill Off The Shoulder Mini Dress
Keep your look casual and chill but still cozy for the cooler months in this off the shoulder mini dress! It features long fitted sleeves, a short, form-hugging fit, and a soft, cashmere-like fabric that offers plenty of stretch. Pair this dress with chunky sneakers for an adorable everyday look.
Fit & Features
- Off the shoulder fold-over neckline
- Long fitted sleeves
- Short, form-hugging fit
- Soft brushed knit fabric with plenty of stretch
- Stretchy knit lining
Style Number/Barcode: 05102-0951
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Back to Basics Knit Mini Dress
Bring it back to basics in a dress that keeps it casual and cute. The dress features a crew neckline, long sleeves, and a mini length silhouette with a rounded hem. The dress is composed of cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Crew neckline
- Long sleeves
- Mini length silhouette
- Rounded hem
- Cotton knit fabric
- Relaxed fit
- Moderate stretch
Style Number/Barcode: 06002-0654
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Plaid Knit Mini Dress
Get a pretty, picture-perfect look in this adorable plaid knit mini dress! It features a trendy square neckline and a short, curve-hugging silhouette. Layer on a chic jacket over this dress and style it up with heeled booties for a fall night out.
Fit & Features
- Spaghetti straps
- Square neckline
- Short, form-hugging fit
- Allover plaid print
- Knit fabric with plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-1049
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Better In Basics Ribbed Knit Sweater Dress
Sometimes, basic is better, like this adorable ribbed knit sweater dress! It features a flattering V neckline, a mid-length, curve-hugging silhouette, and a front slit. Pair this sweater dress with chunky sneakers for a casual-chic vibe.
Fit & Features
- Thin adjustable shoulder straps with gold metal detailing
- V neckline
- Mid-length silhouette
- Form-hugging fit
- Front slit
- Ribbed sweater knit fabric
- Plenty of stretch
Style Number/Barcode: 06005-0862
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance