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

Cute Work Dresses

Floral Print Dresses

Everyday Ease: Casual Dresses for Warm-Weather Plans

From weekend brunches to spontaneous getaways, 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 farmer’s market or catching golden hour with friends.

Laid-Back & Versatile

Lightweight cotton, knit, and chiffon dresses bring comfort and style to sun-filled days. Slip into playful mini dresses, breezy midi styles, or long casual dresses in soft florals, neutrals, and vibrant hues. Tunic and t-shirt dresses with trendy necklines, ruching, or cutouts make “throw on and go” feel totally styled.

Chic from Day to Night

Swap sneakers for strappy sandals to take your favorite midi dress from errands to evening hangs. A flowy maxi in a muted pastel or black adds relaxed elegance—just add a denim jacket and slides for an effortless finish.

Ready to reset your daily 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!

Whimsical Cutie Butterfly Polka Dot Satin Maxi Dress
Soar toward any celebration in this whimsical and cute polka dot satin maxi dress! Featuring cap sleeves and a gorgeous butterfly lace trim sweetheart neckline, this dress adds a touch of elegance. The button-down back with a cutout accent completes the maxi silhouette, making you the center of attention! Complete the look in strappy block heels and a necklace.

Fit & Features
- Polka dot print, satin fabric, no stretch
- Butterfly lace trim sweetheart neckline
- Button-down back and zipper hook-eye closures
- Cutout back accent
- Maxi length silhouette
- Runs true to size
Style Number/Barcode: 05101-3555

Category Name: Casual Dresses

Price: $19.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Effortlessly Chic Button Front Tunic
Create an effortlessly chic everyday look with this classic tunic. It features a collared neckline, a complete button-down front, long sleeves, and a cinched waist effect for a figure-flattering silhouette. Style this tunic with sleek hoops and clear mules.

Fit & Features
- Collared neckline
- Button-down front
- Long sleeves, single-button details
- Cinched waist effect
- Pleating detail
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1497

Category Name: Casual Dresses

Price: $18.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress
An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!

Fit & Features
- Smooth knit fabric lined with stretchy knit
- Spagehtti straps
- Square neckline
- Lace-up
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5689

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Picture Perfect V-Neck Smocked A-Line Midi Dress
You'll be the picture of perfection in this adorable A-line midi dress at showers or birthday brunch! With its flattering V-neckline and stretchy smocked bodice, this dress hugs your body in all the right places. The tie spaghetti straps add a touch of delicacy, while the V-cut waist seam and A-line silhouette create a flattering look along the midi-length hem. Complete the look in espadrille wedges.

Fit & Features
- Woven fabric lined with non-stretch woven
- Tie spaghetti straps
- V-neckline
- Stretchy smocked bodice
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05101-3560

Category Name: Casual Dresses

Price: $11.97 $64.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Perfect Match Sleeveless Striped Ribbed Knit Mini Dress
You and this striped knit mini dress are the perfect match for sunny days! With a playful scoop neckline and cutout back, this mini dress is a cute piece for any fun occasion. Its bodycon fit flatters your figure while the striped pattern adds a touch of quirkiness. The ribbed knit fabric offers a moderate stretch for comfortable wear. Complete the look with flat sandals.

Fit & Features
- Striped pattern
- Ribbed knit fabric with moderate stretch
- Scoop neckline
- Tank shoulder straps
- Cutout back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1940

Category Name: Casual Dresses

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
In The Details Basic Ruched Midi Dress
The true style of this basic midi dress lies in the detail! Features a sleeveless square neckline, sleek bungee spaghetti straps, ruched seams down the sides to accentuate your curves, and a flattering bodycon silhouette. The dress is composed of a brushed soft knit fabric with a full-length lining. Complete the look with a chic handbag for a dinner date.

Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched side seams
- Bodycon silhouette
- Midi-length hem
- Brushed soft knit fabric, lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5146

Category Name: Casual Dresses

Price: $19.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Artsy Play Abstract Mock Neck Mini Dress
Play up your artsy side in this mesh mini dress totally giving those Y2K vibes! The mini dress features fitted long sleeves with split cuffs, a mock neckline, and a bodycon silhouette on mesh abstract printed fabric with a sheer mesh stretchy lining. Complete the look in chunky platform heels for a party!

Fit & Features
- Fitted long sleeves, split cuffs
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Abstract print on mesh fabric, sheer mesh stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5398

Category Name: Casual Dresses

Price: $19.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress
Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.

Fit & Features
- Ribbed knit fabric with moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Twisted bust, cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5280

Category Name: Casual Dresses

Price: $19.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Smooth Silhouette Mock Neck Mini Dress
Turn heads in this essential mini dress! Crafted with a double-lined smooth seamless knit fabric, the mini-length dress fits your body like a glove and features a mock neckline, fitted long sleeves, and a flattering bodycon silhouette. Make a statement and get compliments wherever you go styling this mini dress with combat boots and jacket.

Fit & Features
- Fitted long sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Double mesh lined smooth seamless knit fabric
- Buttery soft and stretchy
- Runs true to size
Style Number/Barcode: 05102-5384

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sensational City Girl Strapless Cargo Mini Dress
Hit the streets with a strapless mini dress that'll make you an instant sensational city girl! The strapless straight-across neckline and bodycon silhouette flatter any figure, while the front button closure and belt loop accents add a trendy touch. With a hidden front zipper, cargo flap pockets, and a mini-length hem, this woven dress is both fashionable and functional. Complete the look in lug boots for casual plans!

Fit & Features
- Cotton-blend woven fabric, minimal stretch
- Strapless straight neckline with belt loop detailing
- Front button closure
- Hidden front zipper closure
- Cargo flap pockets
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5503

Category Name: Casual Dresses

Price: $19.97 $42.90

On Sale: Yes

Availability: In Stock

Available Color: BROWN

Available Size: S, XS
Product Badge:
- Sale
The Best Yet Sleeveless Crew Neck Slit Maxi Dress
The best has come with this stylish basic maxi dress perfect for dressing up or down for any occasion! Crafted from a soft knit fabric, you'll adore this sleeveless dress for its comfort and versatility. The crew neckline gives off a classic vibe while the bodycon silhouette flaunts your curves down to the maxi-length hem with a flirty side slit for movement. Complete the look with a jacket, heels, and a crossbody bag!

Fit & Features
- Soft knit fabric, short lining, plenty of stretch
- Sleeveless crew neckline
- Tank straps
- Side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5588

Category Name: Casual Dresses

Price: $32.90

Availability: In Stock

Available Color: BLACK

Available Size: XS, S, M, L
Make It Sexy Off-The-Shoulder Mini Dress
Show off your curves in this sexy mini dress for weekend outings! The short dress features an off-the-shoulder neckline with a flirty bust keyhole tie, long sleeves with flared cuffs, side ruched seams to accentuate your figure, a bodycon silhouette, and a mini-length hem. Complete the look in lace-up stiletto heels and dare to be bold!

Fit & Features
- Off-the-shoulder neckline, bust keyhole tie
- Long sleeves with flared cuffs
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5212

Category Name: Casual Dresses

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunset Happy Hour Ruffled Skater Dress
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.

Fit & Features
- Sleeveless V-neckline
- Halter tie-back straps, open back
- Stretchy smocked high waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Twill fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-5531

Category Name: Casual Dresses

Price: $46.90

Availability: In Stock

Available Color: YELLOW

Available Size: XS, S, M, L
Cute And Casual Everyday Ribbed Knit Midi Dress
This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.

Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-4934

Category Name: Casual Dresses

Price: $9.97 $22.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Showstoppin' Staple Long Sleeve Maxi Dress
Put your curves on display in this basic maxi dress perfect for dressing up or down! The long dress features fitted long sleeves, a classic crew neck, and a flattering bodycon silhouette on hacci rib knit fabric. Complete the look with strappy heels and a purse!

Fit & Features
- Hacci rib knit fabric, plenty of stretch
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5331

Category Name: Casual Dresses

Price: $6.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Truly Chic High Slit Bodycon Midi Dress
Create a truly chic look for dinner and drinks in this high slit bodycon midi dress! It features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, ruching down the side seams, an asymmetric midi-length hem creating a thigh-high side slit, and a bodycon fit to showcase your stunning silhouette. The lined smooth knit fabric offers plenty of stretch. Style with rhinestone fringe earrings to add a touch of glam!

Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Ruched side seams
- Asymmetric midi-length hem, thigh-high side slit
- Bodycon silhouette
- Smooth knit fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5521

Category Name: Casual Dresses

Price: $6.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
So Fab Marble Print Mesh Mini Dress
Oh so fab, you'll turn heads in this alluring marble print mesh mini dress. It features a sleeveless cowl neckline, adjustable spaghetti straps to customize the fit, a mini-length hem with a cute lettuce-edge trim, and a bodycon silhouette that will hug your natural curves. The airy sheer mesh fabric includes a full knit lining and features an all-over marble print pattern. Style with lace-up heels.

Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Mini-length hem, lettuce-edge trim
- Bodycon silhouette
- Marble print
- Sheer mesh fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5509

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Sweetest Look Ditsy Floral Chiffon Babydoll Dress
Create the sweetest look for your summer plans with this adorable babydoll dress! The airy sheer chiffon fabric is detailed with a ditsy floral print and includes a full-length lining for coverage. The short dress features a sleeveless scoop neckline with ruching at the bust, adjustable spaghetti straps for a customized fit, a smocked back for added stretch, and a ruffled tiered A-line silhouette with an effortless flowy fit. Style with sneakers for a cute and casual summer outfit.

Fit & Features
- Ditsy floral print
- Sheer chiffon fabric with stretchy knit lining
- Ruched scoop neckline
- Adjustable spaghetti straps
- Smocked back
- Ruffled tiered A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5451

Category Name: Casual Dresses

Price: $6.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Right Impression V-Neck Floral Ruffle Skater Dress
A cutie like you will always make the right impression in this floral skater dress on dates or at brunch! Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.

Fit & Features
- Floral print, chiffon fabric with woven lining, no stretch
- V-neckline, V-cut back with spaghetti strap tie
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-2894

Category Name: Casual Dresses

Price: $6.97 $56.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.

Shop More Sweater Dresses: Sweater Dress Collection

Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167

Category Name: Casual Dresses

Price: $16.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Paradise Pick V-Neck Cutout Tropical Maxi Dress
Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.

Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline, keyhole
- Cutout back
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5692

Category Name: Casual Dresses

Price: $24.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Casual Scene Crew Neck Midi Dress
Your next casual plans call for this t-shirt midi dress for grabbing coffee or running errands in style! It features a classic crew neck, short sleeves, a cutout waist with a knot accent, a bodycon silhouette, and a flirty front slit on smooth cotton knit fabric. Complete the look in cute strappy sandals.

Fit & Features
- Crew neck, short sleeves
- Cutout waist, knot accent
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth cotton knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5765

Category Name: Casual Dresses

Price: $9.97 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Cute And Casual Knit Hoodie Dress
This cute and casual knit hoodie dress is perfect for styling up for your weekend plans! It features a hoodie with a front drawstring, long fitted sleeves, and a mini-length, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch for ultra comfortable wear. Complete the look in this short dress with a plaid shacket and combat boots.

Fit & Features
- Hoodie, front drawstring
- Long fitted sleeves
- Mini-length hem
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4798

Category Name: Casual Dresses

Price: $9.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The One You Need Mini Dress
Step out in style with this sexy ribbed knit mini dress, perfect for brunch with your besties or a relaxed weekend outing. Its minimalist bodycon silhouette pairs effortlessly with an oversized denim jacket or a fitted blazer for a look that's polished yet effortlessly chic. The dress's flattering V-neckline is ideal for showcasing delicately layered necklaces, adding a sweet and enchanting touch to your ensemble.

Fit & Features
- Sleeveless V-neckline
- Thin bungee straps
- Strapless bra recommended
- Mini-length bodycon silhouette
- Ribbed knit fabric
- Figure-hugging fit, plenty of stretch
- Runs true to size
Style Number/Barcode: 06002-0500

Category Name: Casual Dresses

Price: $6.97 $24.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale

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