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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Cozy Fave Cable Knit Long Sleeve Mini Dress
Cozy up in the cutest cable knit mini dress featuring a V-neckline, a surplice wrap front and back design, and long dolman-style sleeves. The tie-front high waist and form-hugging fit will highlight your curves, making it your fave dress of the season.
Fit & Features
- Cable knit fabric with plenty of stretch
- V-neckline, surplice front and back design
- Back bar strap
- Long dolman sleeves
- Tie-front waist
- Mini-length form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2101
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
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Sleek Essential Ribbed Knit High Slit Midi Dress
Accessorize a ribbed knit midi dress for the perfect fall outfit. The dress features a plunging V-neckline, long fitted sleeves, and a bold high slit. Complete your outfit with thigh-high boots.
Fit & Features
- Ribbed knit fabric with plenty of stretchÂ
- V-neckline
- Long fitted sleeves
- High side slit
- Midi-length hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-2079
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic And Sleek Knit Off-Shoulder Long Sleeve Midi Dress
Classic and sleek, this stretchy knit midi dress features an asymmetric off-shoulder neckline with long fitted sleeves, ruching at the waist to accentuate your curves, and a bodycon silhouette. Style with stiletto heels for a chic outing!
Fit & Features
- Jersey knit fabric with plenty of stretch
- Asymmetric off-shoulder neckline
- Long fitted sleeves
- Ruched waist
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5977
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
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So Adored Sleeveless Bow Trim Crepe Mini Dress
Embrace romance in this crepe mini dress that features a sleeveless square neckline with tank-like straps, a charming bow accented trim under the bust, and a flared mini-length hem with an A-line silhouette. Complete your look with sleek flats!
Fit & Features
- Crepe fabric with knit lining, moderate stretch
- Sleeveless square neckline, dart seams
- Tank-like shoulder straps
- Bow accented trim under bust
- Back zipper closure
- Flared mini-length hem, A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3840
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
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Out And About Long Sleeve Short Dress
This adorable long sleeve short dress is ideal for those casual days where you're out and about! It features a square neckline with a ruched bust and an adjustable tie-front drawstring, long fitted sleeves, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The lined brushed crepe fabric offers plenty of stretch. Style this short-length dress with a chunky knit cardigan and over-the-knee boots for a coffee date!
Fit & Features
- Square neckline
- Ruched bust, tie-front drawstring
- Long fitted sleeves
- High waist seam
- Short-length hem, A-line silhouette
- Brushed crepe fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5886
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: IVORY
Available Size: L
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Elevated Chic Off-The-Shoulder A-Line Mini Dress
Elevate any casual day in this off-the-shoulder mini dress! This stunning dress features a twisted bust accent for a trendy touch, an A-line silhouette, and a mini-length hem that creates a flattering fit on the smooth knit-lined fabric. Complete the look with luxe earrings for a dinner party!
Fit & Features
- Smooth knit lined fabric, moderate stretch
- Off-the-shoulder neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5755
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: BLACK
Available Size: M, L
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Chic Moment Off-The-Shoulder Bell Sleeve Mini Dress
An off-the-shoulder mini dress that'll give you many chic moments! The crepe dress is designed with long fitted bell sleeves with flirty tie accents and a front slit for movement. Complete the look with a necklace.
Fit & Features
- Viscose crepe knit fabric with knit lining, moderate stretch
- Off-the-shoulder sweetheart neckline, can be worn on the shoulder
- Long fitted bell sleeves, tie accents
- Front slit
- Mini-length hem
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5881
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
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Casual Muse Scoop Neck Mini Dress
A casual mini dress that's sure to become your fashion muse! The mini-length dress features fitted long sleeves, a scoop neckline, a built-in shelf bra for extra support, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look in a moto jacket and boots for day or evening plans!
Fit & Features
- Fitted long sleeves
- Scoop neckline
- Built-in shelf bra
- Bodycon silhouette, mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5244
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
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Standout Staple Crew Neck Cutout Midi Dress
This midi dress may just become that special staple piece in your lineup! It features fitted long sleeves, a crew neck with a button-back closure and keyhole accent, a flattering bodycon silhouette and front slit, and a flirty cutout back design. Complete the look with statement earrings for a cocktail hour.
Fit & Features
- Fitted long sleeves
- Crew neck, back button closure, keyhole
- Bodycon silhouette, front slit
- Cutout back design
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5335
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S
Product Badge:- Sale
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Sleek Silhouette Ribbed Knit Off-The-Shoulder Midi Dress
Showcase a sleek silhouette in this ribbed knit midi dress featuring an off-the-shoulder neckline with a fold-over design and a mermaid silhouette to highlight your curves. Style with knee-high boots for a chic look.
Fit & Features
- Ribbed knit fabric, plenty of stretch
- Off-the-shoulder neckline
- Fold-over design, short sleeves
- Midi-length mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5896
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simply Amazing Long Bell Sleeve Mini Dress
A simply amazing little black dress you'll adore wearing on dressy occasions! It features a square neckline, long bell sleeves with trendy ruched adjustable ties and slit accents, a flattering bodycon silhouette, and a mini-length hem. The dress is composed of a double-lined soft brushed knit fabric. Complete the look with a chic mini purse and heels.
Fit & Features
- Double-lined soft brushed knit fabric
- Moderate stretch
- Square neckline
- Long bell sleeves, ruched adjustable ties, slit accents
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5890
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: L
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Endlessly Effortless Crew Neck Abstract Midi Dress
You'll always look and feel perfect in this sleeveless midi dress for parties or going out! Crafted from an abstract print mesh fabric, this dress boasts a crew neckline, a flattering bodycon silhouette, and a midi-length hem. Complete the look in stiletto heels and a purse!
Fit & Features
- Abstract print, mesh fabric, soft knit lining
- Crew neckline
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5819
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Expression Sleeveless Plaid Mini Dress
A sleeveless plaid mini dress features a flattering square neckline with a satin bow, shoulder straps, and a bodycon silhouette. Perfect for back-to-school styling.
Fit & Features
- Plaid woven fabric, bust lining, minimal stretch
- Square neckline with satin bow
- Shoulder straps
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-5825
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
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High Appeal Mock Neck Bodycon Mini Dress
A must-have basic for the upcoming season! This dress features fitted long sleeves, a mock neck, a flattering bodycon silhouette, and a mini-length hem. It's composed of a cotton-blend knit fabric with a moderate stretch for comfort. Complete the look in strappy heels for a birthday brunch!
Fit & Features
- Fitted long sleeves
- Mock neck
- Bodycon silhouette
- Mini-length hem
- Cotton-blend knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5152
Category Name: Casual Dresses
Price: $26.90
Availability: In Stock
Available Color: CHARCOAL
Available Size: S, M, L
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Lost In Love Strappy Back A-Line Mini Dress
Everyone will be lost in love once they catch sight of you in this strappy A-line mini dress! Perfect for any occasion, this dress will have you feeling fabulous. This playful A-line mini features a flattering sweetheart neckline, shoulder straps for added support, and a strappy back for flirty fun. Complete the look in block heels.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Sweetheart neckline
- Shoulder straps
- Strappy back
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5544
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chicly Femme Bodycon Abstract Mesh Midi Dress
A sleeveless midi dress features a square neckline and a bodycon silhouette that flaunts your curves. The abstract print mesh fabric offers an artsy look. Perfect for styling with stilettos.
Fit & Features
- Abstract print, mesh fabric
- Square neckline
- Spaghetti straps
- Bodycon midi-length fit
- Runs true to size
Style Number/Barcode: 05102-5580
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L, XL
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Stunning Sweetie Open Back Bow Skater Dress
Arrive like the stunning sweetie you are in this short skater dress as the bride-to-be, graduate, or birthday girlie! This dress features a square neckline and shoulder straps, with an attention-grabbing open back and statement bow detail. The drop waist skater silhouette is flattering, and the short-length hem is perfect for showing off your legs. Complete the look in block heels.
Fit & Features
- Woven fabric, tulle and stretchy knit lining
- Square neckline, shoulder straps
- Open back, statement bow
- Back zipper and hook-eye closure
- Drop waist seam, skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3410
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Colorful Essence Sleeveless Marble Print Mini Dress
You'll be the most colorful babe on the scene in this marble print mini dress! Perfect for art gallery openings and date nights, this sleeveless dress boasts a square neckline, adjustable spaghetti straps for a custom fit, and side ruched seams and a bodycon fit to accentuate your curves. Complete the look with a clutch and stiletto heels.
Fit & Features
- Marble print, mesh fabric, sewn-in knit lining, moderate stretch
- Square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5691
Category Name: Casual Dresses
Price: $42.90
Availability: Out of Stock
Product Badge:- Sale
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Easy Bliss Turtleneck Striped Mini Dress
This sleeveless knit mini dress boasts a turtle neckline and a bodycon silhouette with a trendy striped pattern. Style with simple hoop earrings for any casual plans.
Fit & Features
- Striped pattern, stretchy knit fabric
- Turtle neckline
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 06005-2045
Category Name: Casual Dresses
Price: $7.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Long Sleeve Ruched Mini Dress
Embrace your curves in this must-have mini dress! The short dress features fitted long sleeves and a scoop neckline for a flattering look, while the side ruched seams and bodycon silhouette accentuate your curves. Crafted from a double-lined buttery soft fabric that fits like a glove with plenty of stretch. Layer with a jacket and a trendy shoulder bag to complete the look!
Fit & Features
- Fitted long sleeves
- Scoop neckline
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Double-lined buttery soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5519
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: PINK
Available Size: L
Product Badge:- Sale
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Casual Luxe Long Sleeve Ribbed Knit Mini Dress
Part casual, part luxe, this long-sleeved mini dress is perfect for your next date night! The ribbed knit dress features a square neckline, long sleeves, and a mini-length hem. Complete look with knee-high boots!Â
Fit & Features
- Ribbed knit fabric with knit lining, plenty of stretch
- Square neckline
- Long fitted sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5899
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Carefree Chic Long Sleeve Ribbed Knit Midi Dress
An off-the-shoulder midi dress perfect for those carefree days! It features fitted long sleeves and a bodycon fit that shows off your curves. Pair with sneakers.
Fit & Features
- Ribbed knit fabrication, stretchy knit lining
- Off-the-shoulder neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5924
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: In Stock
Available Color: DARK, MARSALA
Available Size: S, M, L
Product Badge:- Sale
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Cute Flirt Drop Waist Ruffled Hem Mini Dress
Show off your stunning figure in this smooth knit mini dress featuring a boat neckline, long fitted sleeves, a cute scoop back, a drop waist design, and a short tiered ruffled hem with an A-line fit for that flirty flair. Style with strappy mules!
Fit & Features
- Smooth nylon knit fabric, plenty of stretch
- Boat neckline
- Long fitted sleeves
- Scoop back
- Drop waist
- Tiered ruffled mini-length hem, A-line fit
- Runs true to size
Style Number/Barcode: 05102-5938
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Sale
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Serving Chic Long Bell Sleeve A-Line Mini Dress
Serve chic looks in this A-line mini dress featuring a halter V-neckline with flirty cutouts and long fitted bell sleeves to give coverage. Style with earrings.
Fit & Features
- Smooth knit fabric with partial lining, plenty of stretch
- Halter V-neckline, tie-back spaghetti straps
- Cutout shoulder design
- Long fitted bell sleeves, slit accents
- Lower back cutout
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3657
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: M
Product Badge:- Sale