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.

HomeCasual Dresses

STYLE SPOTLIGHT

Cute Sweater Dresses

Floral Print Dresses

Discover New Skater Dress Styles

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!

Basic Scoop Mini Dress
Basic never looked so good in this essential mini dress! It features a light blue color, a scoop neckline, tank-like straps and a mini length silhouette. Dress is composed of a double lined smooth knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3350

Category Name: Casual Dresses

Price: $13.91 $23.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
On The Button Denim Mini
Streamlined and sweetly sophisticated, this lavender mini draws all eyes to you. Dress features a soft V neckline, button front, and adjustable spaghetti straps. Dress is made from a cotton-denim fabric and has minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-0116

Category Name: Casual Dresses

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Button Down In Style Dress
Button down in style in this cute midi dress! The white dress features a square neckline, wide shoulder straps, a button down front, a tie waist belt, side pockets and a center high slit. Dress is composed of an unlined denim-like fabric that offers a form hugging fit with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-0059

Category Name: Casual Dresses

Price: $31.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Striped With Style Midi Dress
Get all striped with style with this adorable summer ready midi dress! It features a sleeveless bodice, a V neckline created by a wrap front, a partially stretchy and smocked back with a hidden zipper and hook and eye closure, a faux button down front, a waist tie, and a front slit. The mustard yellow dress is composed of lightweight woven fabric with no stretch and a short lining.
Model is 5'8" with a 33" bust, 24" waist and 33.5" hips. She is wearing a size small.

Style Number/Barcode: 05102-0032

Category Name: Casual Dresses

Price: $15.00 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Sunny Side Up Skater Dress
This mustard yellow skater sundress is a definite must-have for this season! It features a sleeveless bodice, adjustable spaghetti straps, a square neckline, a hidden back zipper and hook and eye closure, a high waist seam, and a wrap skater skirt with a chic side tie. The dress is composed of a woven fabric with no stretch.
Model is 5'8" with a 33" bust, 24" waist, and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-0054

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Buttoned Up In Stripes Dress
Button up in stylish stripes! This pretty dress features a plunging V neckline, kimono sleeves, a cinching tie waist accent and a multi button down front with tortoise shell hued buttons that lead to an A-Line silhouette. The back features a matching plunging V shape, an adjustable bar strap detail and a hidden zipper closure. The all over stripe pattern features blue and white hues. Dress is composed of a lined gauze fabric that offers a relaxed fit with minimal stretch.

Style Number/Barcode: 05102-0040

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
All Eyes On You Mini Dress
All eyes will be on you in this adorable eyelet mini dress! It has short puffy sleeves with elastic cuffs, a square neckline, faux button down details, a hidden zipper and hook and eye closure, a high waist seam, and a short, fitted look. The ivory dress is composed of a woven sheer eyelet fabric with a full lining.
Model is 5'8" with a 33" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-0001

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Floral Frenzy Open Back Maxi
Get caught up in pretty florals! This gray maxi dress features a sleeveless bodice, a square neckline, narrow shoulder straps and an open back with a narrow bar strap accent. The relaxed fit bodice leads to a curve hugging maxi length silhouette. The all over floral print is all you need to create a sweet look! Dress is composed of a knit fabric that offers a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05102-0004

Category Name: Casual Dresses

Price: $13.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Hourglass Mini Dress
Get those golden hour selfies with this perf mustard yellow mini dress! It features a square neckline and back, short ruffle sleeves, a hidden back zipper and hook and eye closure, a high waist seam with two cut outs, and a woven lining. The dress is composed of a woven fabric with a floral eyelet pattern and no stretch.

Style Number/Barcode: 05102-0003

Category Name: Casual Dresses

Price: $10.00 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ruffled Floral Mini Dress
This ruffled floral mini dress couldn't be more spring-ready! It features an off the shoulder sweetheart neckline with light padding and a ruffle overlay, a high waist seam, and a short, form hugging fit. The ivory dress is composed of a scuba knit fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8713

Category Name: Casual Dresses

Price: $10.00 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring With Florals Maxi Dress
Step out this season in pretty florals to make a charming impression! The ivory maxi dress features an off the shoulder neckline with the off the shoulder strap accents, a straight bust, a cinching tie waist belt and maxi length silhouette with a high side slit. The back features a lower back keyhole. The all over floral print features pink hues. Dress is composed of a lightweight woven fabric that offers a form hugging fit with minimal stretch. Includes an additional mini skirt length lining.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small

Style Number/Barcode: 05101-8699

Category Name: Casual Dresses

Price: $19.97 $48.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
What's Up Buttercup Maxi Dress
You're lookin' like a ray of sunshine in this mustard yellow maxi dress! It has an off the shoulder neckline with draped ruffle sleeves, a high waist seam with a tie belt and back cut out, and a flowy, floor-length wrap skirt that creates a high leg slit. Dress is composed of a gauze fabric. Includes exposed back zipper closures and a short knit lining.
Model is 5'8" with a 32" bust, 24.5" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8658

Category Name: Casual Dresses

Price: $10.00 $52.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
In Your Pipe Dreams Midi Dress
You're the ultimate dream girl in this flattering midi dress! It has a deep V neckline, spaghetti straps leading to a square back and exposed zipper and hook and eye closure, and perfectly placed piping throughout to create a shape that complements this dress' body-hugging silhouette. Midi dress is composed of a natural-colored knit fabric and offers moderate stretch.
Model is 5'9" with a 31.5" bust, 24.5" waist and 35.5" hips. She is wearing a size small.

Style Number/Barcode: 05101-8666

Category Name: Casual Dresses

Price: $15.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sassy Sweet Floral Chiffon Ruffled Skater Dress
Sassy and sweet, this floral chiffon skater dress will be your new brunch go-to! The strapless smocked bodice and ruffled skater silhouette are feminine details you'll adore.

Fit & Features
- Chiffon fabric, stretchy knit lining
- Small floral print
- Strapless straight neckline
- Smocked bodice
- High waist seam
- Tiered ruffled design, short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5967

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Passionate About Florals Maxi Dress
Show your passion for pretty florals in this captivating maxi dress! It features a navy blue hued smocked bodice with a sweetheart neckline and leads to a sweeping maxi length silhouette. The skirt features a head turning floral print with coral and blue hues that contrast with the ivory hued background. Dress is composed of a combination smock and chiffon knit fabric that offers a relaxed fit.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-8178

Category Name: Casual Dresses

Price: $10.00 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Ruffle My Feathers Mini Dress
Channel effortless warm-weather style in this fun, flirty dusty pink mini dress. Dress has thick straps, a sweetheart neckline with a small V, side smocking, a hook-and-eye zip closure, and a flared hem. Dress is made from a linen-like fabric with generous stretch at sides.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05101-0090

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Blair One Shoulder Cut Out Dress
Special Occasion
Stand out in our statement making Blair dress! She features a chic black hue, a one shoulder neckline, a sexy waist cut out to create a cropped illusion and a curve hugging floor length silhouette that is accented with a high side slit and ruching. Dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Includes a mini skirt length knit lining.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.

Style Number/Barcode: 05002-6749

Category Name: Casual Dresses

Price: $29.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Basic Essentials Midi Dress
Sometimes less is more! This basic midi length can be kept casual or paired with accessories to dress it up!

Fits & Features
- Tank Shoulder Straps
- Scoop Neckline
- Midi Length Silhouette
- Soft Knit Composition I Fully Lined
- Curve Hugging Fit I Ample Stretch
Black & Ivory: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-3587

Category Name: Casual Dresses

Price: $24.90

Availability: Out of Stock
Product Badge:
- Clearance
Sun Coast Dream Paisley Bodycon Slit Maxi Dress
Enjoy a vacay or day out by the sunshine coast in this paisley maxi dress with a flattering bodycon fit and side slit for effortless movement!

Fit & Features
- Paisley boho print, mesh fabric, sewn-in brushed knit lining
- Square neckline
- Spaghetti straps, criss cross back
- Bodycon silhouette
- High side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-5928

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Fave Floral Ruffled Skater Dress
This adorable ditsy floral skater dress will be your new flirty fave to style up all season! You'll love the tiered ruffled design and flowy fit-and-flare silhouette.

Fit & Features
- Woven fabric
- Ditsy floral print
- Strapless straight neckline
- Smocked bodice
- Tiered ruffled skater silhouette
- Short-length hem
- Runs true to size
Style Number/Barcode: 05102-6052

Category Name: Casual Dresses

Price: $9.97 $54.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Flirty Effect Cap Sleeve Bodycon Floral Mini Dress
You'll have a flirty effect in this floral bodycon dress boasting pretty details like flattering cap sleeves, a tied bust, and a ruffled mini hem.

Fit & Features
- Floral print, eyelet knit fabric, stretchy knit lining
- Cap sleeves
- Sweetheart neckline, tied bust
- Bodycon silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6051

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Vacay Bound Tropical Floral Ruched Knit Maxi Dress
Make sure to pack this tropical floral knit maxi dress for your next sunny vacay! The ruched bodycon silhouette will flaunt your stunning curves as you pose for those getaway pics.

Fit & Features
- Ribbed knit fabric, high stretch
- Tropical floral print
- Sleeveless cowl neckline
- Spaghetti straps
- Ruching
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6054

Category Name: Casual Dresses

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
The Essential High-Slit Ribbed Knit Midi Dress
The ribbed knit dress features a turtleneck, fitted long sleeves, and a midi-length hem accented with a high side slit. Pair it with ankle booties to complete the look.

Fit & Features
- Ribbed knit fabrication, stretchy knit lining
- Turtleneck
- Long sleeves
- High side slit
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5959

Category Name: Casual Dresses

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Somewhere Tropical V-Neck Cutout Abstract Maxi Dress
This maxi dress plus you somewhere tropical equals the chicest vacation! The dress boasts a trendy cutout with a decor accent and a sultry side slit for effortless movement.

Fit & Features
- Abstract print, stretchy knit-lined fabric
- V-neckline with decor accent
- Spaghetti straps
- Cutout bodice, side slit
- Bodycon silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6055

Category Name: Casual Dresses

Price: $20.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

Reset Your Password

Email Sent

Order Status

Casual Dresses