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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Attention-Worthy Camo Print Bodycon Mini Dress
Create an attention-worthy 'fit in this camo-printed woven mini dress featuring a strapless straight-across neckline accented with dual flap pockets, a secure back zipper closure, cargo-style pockets on each side, and a bodycon silhouette to showcase your curves. Complete the look with a bomber jacket and combat boots!
Fit & Features
- Camouflage printed twill woven fabric
- Strapless straight neckline, dual flap pocket accents
- Back zipper hook-eye closure
- Dual cargo flap pockets
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5909
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tie Dye Frenzy Brushed Knit Mini Dress
Make a splash in a tie-dye dress that brings the style to your next outing! The mini dress features a round neckline, a slash accent on the left side of the bodice, and a tie-dye print. Style this fun print with chunky sneakers and sleek hoops.
Fit & Features
- Round neckline
- Slashed detail on the left side of the bodice
- Short sleeves
- Tie-dye print
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 06002-0581
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Knit Retro Tie Dye Ruched Mini Dress
Keep it retro in a tie-dye dress to brighten up your outfits! The mini dress features a mock neck with a zipper front, a tie-dye print, and a mini length silhouette complemented with ruched side seams. Complete your look with clear mules.
Fit & Features
- Mock neck with zippered front
- Long sleeves
- Tie-dye print
- Mini length silhouette
- Ruched side seams
- Form hugging fit
- Moderate stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-1013
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keeping Knit Chic Mock Neck Ruched Mini Dress
Keep it chic in a ruched dress that elevates your night out outfit! The dress features a mock neck, fitted long sleeves, and a ruched side drawstring. Complete your night out look with clear heels.
Fit & Features
- Mock neck
- Fitted long sleeves
- Ruched side drawstring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0904
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Knit Real Ruched Mini Dress
Keep it real in this chic mini dress for your next outing with the squad! The dress features a crew neckline, ruched side seams with drawstrings at the hem, and a curve-hugging mini-length silhouette. Complete your look with mules.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched side seams
- Drawstrings at the hem
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
Style Number/Barcode: 05102-0921
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Major Influence Mock Neck Ruched Mini Dress
Hey, trendsetter! Stun in this mini dress that is so chic and casual! The mini dress features a sleeveless mock neck, a ruched body and a mini length silhouette that hugs curves in all the right places. Style with chunky sneakers to nail those lowkey vibes.
Fit & Features
- Sleeveless
- Mock neck
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0886
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feline Fashionista Leopard Mesh Mini Dress
Keep it fierce in a leopard dress that shows off your affinity for style! The mini dress features a leopard print, a sleeveless square neckline, and sleek spaghetti straps. Complete your night-out look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Leopard print pattern
- Mini-length silhouette
- Lined mesh fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-0927
Category Name: Casual Dresses
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Get Knit Right High Slit Maxi Dress
Get your look right in a knit dress that is perfect for keeping it casual! The dress features a sleeveless crew neckline and a maxi length silhouette with a high side slit. Complete your look with chunky sneakers for a cute coffee run outfit.
Fit & Features
- Crew neckline
- Sleeveless
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 05102-0883
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty In Plaid Woven Mini Dress
Keep it pretty in a plaid dress that is so on trend this season! The dress features a sleeveless square neckline, a plaid print, and a mini length silhouette. Complete your cute date night look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Woven fabric
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 05102-0891
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovin' Knit Basic Midi Dress
We love a knit dress to keep on trend this season! Throw on this must-have dress for a casual day out. The dress features a trendy square neckline, fitted long sleeves, and a midi length silhouette. Complete look with chunky sneakers for a casual vibe.
Fit & Features
- Square neckline
- Long sleeves
- Midi length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0853
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good Vibes Basic Ribbed Knit Maxi Dress
Bring the good vibes in a maxi dress that can be dressed up for a chic day out. The dress features a scoop neckline, sleek bungee straps, and a maxi length silhouette with a high side slit. Style dress with chunky sneakers and sleek hoops.
Fit & Features
- Sleeveless scoop neckline
- Bungee spaghetti straps
- Maxi length silhouette
- High side slit
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0863
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buttoned In Sassy Stripes Midi Dress
Button up in a striped dress that keeps your look so casually cute! The dress features a fab button-down front, tie spaghetti straps, and a striped pattern. Complete your look with clear mules for a stylish look.
Fit & Features
- Sleeveless scoop neckline
- Tie spaghetti straps
- Button-down front
- Striped pattern
- Midi length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0569
Category Name: Casual Dresses
Price: $9.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's A Showstopper Ruched Midi Dress
Make them stop and stare at this stunning dress that commands attention! The sleek midi dress features a trendy square neckline, sleek bungee straps, and a curve-hugging ruched midi silhouette. Complete your look with duster earrings for your night-out outfit.
Fit & Features
- Sleeveless square neckline, bungee straps
- Strapless bra recommended
- Side ruched detailing
- Midi-length bodycon silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0848
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 Casual Off the Shoulder Ribbed Mini Dress
Keep it casual and fab in a mini dress that is so easy to style for your next day out with the squad. The dress features an off the shoulder neckline with a popover detail and composed of a ribbed knit fabric that enhances curves with a moderate stretch. Complete your casual outfit with ankle booties and hoop earrings.
Fit & Features
- Off the shoulder neckline
- Popover detail
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0859
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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So Into You Basic Knit Midi Dress
We're so into this dress that can be dressed up for a date night or keep it casual with layers. The dress features a sleeveless square neckline, tank-straps that offer support, and a curve-hugging midi-length silhouette. Complete look with ankle booties or mules.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Midi length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0912
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Western Style Horse Tapestry Mini Dress
Channel that western-chic style in this mini dress designed with a detailed horse tapestry fabric. The lace-up back offers a customized fit, while the short A-line silhouette is perf for pairing with cowboy boots.
Fit & Features
- Horse tapestry woven fabric, no stretch, knit lining
- Strapless straight-across neckline, no-slip strip
- Lace-up back design
- Lower back cutout, hidden zipper with hook-eye closure
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000200
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bohemian Chic Lace Off-The-Shoulder Skater Dress
Channel that bohemian chic aesthetic in this airy sheer lace skater dress featuring an off-the-shoulder straight neckline with a fold-over design and sheer long fitted sleeves. The trendy V-shaped drop waist seam leads to a short uneven hem with a flowy skater silhouette.
Fit & Features
- Sheer lace fabric with partial knit lining, plenty of stretch
- Off-the-shoulder straight neckline with fold-over design
- Sheer long fitted sleeves
- V-shaped drop waist seam
- Short uneven hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3714
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Slay Every Day Basic Scoop Neck Midi Dress
Slay every day in a basic midi dress that is effortlessly chic. The dress features a sleeveless scoop neckline, tank-straps, and a midi length silhouette. The double lined smooth knit fabirc offers a comfortable feel. Complete your look with chunky sneakers and stud earrings to nail low-key vibes.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Midi length silhouette
- Double lined smooth knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0908
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Essential Ribbed Tube Mini Dress
Keep it casual in a tube dress that keeps your look effortlessly on point. The dress features a sleeveless straight neckline and a tube silhouette. Complete look with sneakers and shimmering hoops.
Fit & Features
- Sleeveless square neckline
- Tube silhouette
- Mini length
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0887
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Every Day Basic Knit Mini Dress
Keep cute in a basic mini dress that is perfect for dressing up or dressing down for a casual day out. The dress features a sleeveless square neckline, tank-like straps that offer support, and a mini length silhouette. Complete your casually cute outfit with sneakers and door knocker earrings.
Fit & Features
- Sleeveless square neckline
- Tank-like straps
- Mini length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0854
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off The Shoulder Ribbed Cutout Mini Dress
Stun in a mini dress that showcases curves in all the right places. Perfect for your next date night, this ribbed dress is a must! The dress features an off the shoulder neckline, fitted long sleeves, and a mid-drift cutout to show off a hint of skin. The dress is composed of a ribbed knit fabric with vertical seams that streamline the silhouette. Complete your night out outfit with hoop earrings.
Fit & Features
- Off the shoulder neckline
- Fitted long sleeves
- Mid-drift cutout
- Vertical seams
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0820
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In Knit For A Good Time Basic Mini Dress
Throw on this basic mini dress and let the good vibes flow! This knit dress is perfect to dress up or dress down for your next date night or for GNO with the squad. The dress features a trendy square neckline, sleek bungee straps, and a mini-length silhouette. Dress up with mules or keep it casual in sneakers.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0873
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Ribbed Knit Basic Mini Dress
Basic yet still so chic, this ribbed knit mini dress is an everyday essential! It features a doubled ribbed knit fabric for comfortable wear and a form-hugging fit to enhance your curves. Pair this adorable dress with some chunky sneakers to get that effortless vibe.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Doubled ribbed knit fabric
Style Number/Barcode: 05102-0841
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flowy Fall Feels Off The Shoulder Tunic
Get those fall feels in this adorable flowy off the shoulder tunic! It features long flowy flared sleeves and a cinched elastic waist. The lightweight woven fabric features a gorgeous allover bohemian floral print. Pair this tunic with some heeled mules for the perfect date night look.
Fit & Features
- Off the shoulder boat neckline
- Long flowy flared sleeves
- Cinched elastic waist
- Short, ruffle hem
- Woven fabric with allover floral print
Style Number/Barcode: 06003-1017
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance