Casual Dresses
Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.
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STYLE SPOTLIGHT
Effortlessly Chic Casual Dresses for Spring and Summer
Refresh your warm-weather wardrobe with stylish and easygoing casual dresses from Windsor. Whether you're heading to brunch, running errands, or meeting friends for a relaxed day out, our collection offers effortless styles that keep you looking put-together with minimal effort.
This season, embrace breezy silhouettes and lightweight fabrics designed for comfort and movement. Choose from flowy midi and maxi dresses in fresh floral prints, playful minis in vibrant hues, and sleek knit dresses perfect for everyday wear. Stay on-trend with tunic and t-shirt dresses featuring stylish necklines, cutouts, and ruching details that elevate your casual looks.
Looking for a dress that easily transitions from day to night? A flattering midi dress in a soft, breathable fabric is your go-to for a chic yet comfortable outfit. Style it with white sneakers for a casual afternoon or swap them for strappy sandals to take your look into the evening.
Long casual dresses are a must-have for those easy summer days. Opt for flowy maxi styles in soft pastels or classic neutrals for an effortlessly polished vibe. Go for classic black for an ultra-versatile look. Pair your casual maxi with a denim jacket and trendy slides for a stylish yet relaxed ensemble.
If you love cozy yet chic styles, these styles are polished yet cozy, perfect for a casual yet refined outfit during transitional weather. Pair it with ankle booties for an effortless spring-to-summer transition.
No matter your plans, finding a versatile dress that fits your personal style has never been easier. From relaxed weekend outings to spontaneous getaways, our selection of everyday dresses is designed to keep up with your plans while keeping you stylish and comfortable. Explore our casual dresses online, in-app, or in-store today!
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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Flawless Style Knit Off-The-Shoulder Long Sleeve Mini Dress
Show off your stunning curves in this form-hugging mini dress made with pointelle knit fabric with plenty of stretch. It features a chic off-the-shoulder neckline with a fold-over design, long fitted sleeves, and ruched side seams along the short bodycon silhouette.
Fit & Features
- Pointelle knit fabric with knit lining, plenty of stretch
- Off-the-shoulder neckline with fold-over design
- Unlined long fitted sleeves
- Ruched side and back seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5917
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M
Product Badge:- Sale
- Pointelle knit fabric with knit lining, plenty of stretch
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Sharp Lines Asymmetrical Long Sleeve Midi Dress
Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look!
Fit & Features
- Ribbed knit fabrication
- Asymmetrical off-the-shoulder neckline
- Pleated popover accent at the neckline
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5947
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: In Stock
Available Color: IVORY
Available Size: L
Product Badge:- Sale
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Luxe Charm Cashmere Knit Hanky Hem Mini Dress
Channel a luxe aura in a ribbed cashmere-like knit dress that features a boat neckline, long fitted sleeves, a partially open back design, and a short hanky hem with an A-line silhouette. Complete the look with knee-high boots and leg warmers for a chic moment!
Fit & Features
- Ribbed cashmere-like knit fabrication, moderate stretch
- Boat neckline
- Long fitted sleeves
- Partial open back, tie-back spaghetti straps
- Mini-length hanky hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6053
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Vibes Long Sleeve Ruched Midi Dress
Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour!
Fit & Features
- Smooth knit fabrication, double-lined
- Boat neckline
- Long sleeves with thumb holes
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3954
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Glam Ribbed Knit Long Sleeve Mini Dress
The ribbed knit dress features a mock neck, long sleeves accented with thumb holes, and a mini-length hem. For a casually glam vibe, complete the look with ankle booties.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Mock neckline
- Long fitted sleeves with thumb hole accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6014
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Button-Down Drop Waist Mini Dress
So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.
Fit & Features
- Textured knit fabric, sewn-in knit lining
- Square neckline
- Tank shoulder straps
- Button-down front
- Drop waist
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3842
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Sleek Vibes Off The Shoulder Knit Midi Dress
Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch!
Fit & Features
- Lined ribbed knit fabrication
- V-neckline and off-the-shoulder
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5942
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: IVORY
Available Size: L, XL
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Adorable Stunner Strapless A-Line Mini Dress
You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.
Fit & Features
- Crepe fabric, stretchy knit lining
- Contrast color block outline
- Strapless straight neckline
- High waist seam
- Back zipper closure
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3801
Category Name: Casual Dresses
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cosmic Chic Tie-Dye Knit Midi Dress
The ribbed knit dress features a scoop neckline, fitted long sleeves, a tie-dye pattern, and a midi-length hem accented with a center slit at the hem. Complete the look with ankle booties for a casually chic vibe.
Fit & Features
- Ribbed knit fabrication
- Scoop neckline
- Long sleeves
- Tie-dye pattern
- Center slit at back of hem
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2132
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Best Seller
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All Things Cozy High Slit Knit Midi Dress
Oh-so-cute and cozy, this knit midi dress is a seasonal staple. It features a mock neckline, long fitted sleeves, an asymmetric mid-length hem creating a thigh-high side slit, and a form-hugging silhouette. The ribbed hacci knit fabric has an ultra-soft feel with plenty of stretch. Style this midi dress with knee-high boots for a latte date.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Asymmetric mid-length hem
- Thigh-high side slit
- Form-hugging fit
- Ribbed hacci knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5333
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: COGNAC
Available Size: S
Product Badge:- Sale
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Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress
Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5894
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: HEATHERGRAY
Available Size: L
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: $46.90
Availability: In Stock
Available Color: TAUPE
Available Size: XS, S, M, L
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Casual Perfection Long Sleeve Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Ribbed knit fabric, knit lining, plenty of stretch
- Square neckline
- Long fitted bell sleeves, flared hems
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5889
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Staple Ribbed Knit Bell Sleeve Mini Dress
This adorable ribbed knit mini dress will be your fave staple of the season featuring a square neckline, long bell sleeves, and a short form-hugging silhouette. Style with knee-high boots for a casual party.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Square neckline
- Long bell sleeves
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2086
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Embrace Cable Knit Midi Dress
Embrace a cozy vibe in a cable knit dress that features a trendy v-neckline, fitted long sleeves, and a midi-length hem. Complete look with ankle booties!
Fit & Features
- Unlined cable knit fabrication
- V-neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2097
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Layered In Glam Ribbed Knit Long Sleeve Maxi Dress
Nail that layered look in a ribbed knit dress featuring a plunging square neckline, a bralette inset with lace trim, fitted long sleeves, and a maxi-length hem with a back slit accent. Complete the look with trendy ankle booties for the ultimate vibe.
Fit & Features
- Ribbed knit fabrication, plenty of stretch
- Square neckline
- Bralette inset with lace trim
- Fitted long sleeves
- Long hem length
- Back slit
- Runs true to size
Style Number/Barcode: 05102-5848
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Glam Abstract Ruched Midi Dress
Step out and mesmerize in a midi dress that features a sleeveless square neckline, ruching throughout to enhance curves, and an abstract marble print. Complete look with strappy heels for a look that's ready for date night!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Ruching
- Abstract marble print
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5937
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
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Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.
Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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: $44.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Social Butterfly Square Neck Floral Mini Dress
A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!
Fit & Features
- Woven fabric lined with stretchy knit
- Butterfly floral print
- Adjustable spaghetti straps
- Ribbon trim, front metal closures
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5623
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Leopard Print Woven A-Line Midi Dress
Trendy and elevated, this leopard-printed woven midi dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, and a partially smocked back for added stretch. The high front slit adds a bold vibe to the mid-length A-line silhouette.
Fit & Features
- Leopard-printed woven fabric, no stretch
- Square neckline, underbust seam
- Adjustable spaghetti straps
- Partially smocked back design
- High front slit
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5923
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twist Of Chic High-Slit Knit Midi Dress
Bring a twist of chic to the every day with a midi dress that features an asymmetrical one-shoulder neckline with a trendy twist shoulder accent and a daringly high side slit. Complete look with slingback shoes to take you from the office to happy hour!
Fit & Features
- Stretchy knit fabrication
- Asymmetrical one-shoulder neckline
- Twist shoulder strap accent
- High side slit
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5983
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: S, M, L
Product Badge:- Sale
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On The Down Low Denim Strapless Midi Dress
Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!
Fit & Features
- Strapless neckline
- Stretchy smocked back
- Button-down front closures
- Bodycon silhouette, midi-length hem
- Belt loop accents, three-pocket styling
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5283
Category Name: Casual Dresses
Price: $5.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale