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.

Casual Dresses Made for Everyday Fall Plans

Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.

Easy Prints, Textures & Layers for the Season

Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.

What Makes a Dress Casual?

A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.

How Do You Transition a Casual Dress From Summer to Fall?

Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.

Which Fabrics Work Best for Everyday Dresses?

Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.

How Can You Style One Casual Dress for Different Plans?

Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.

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
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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
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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
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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:
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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:
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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:
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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:
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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:
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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
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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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:
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Vacay Vibe Tropical Floral Halter Maxi Dress
You'll be a total vibe on your summertime vacay in this tropical floral print maxi dress. The plunging halter neckline, ruched side seams, and curve-hugging fit are all alluring details you'll love.

Fit & Features
- Knit fabric with knit bust lining, high stretch
- Tropical floral print
- Sleeveless plunge V-neckline
- Tie-back halter straps, partially open back
- Ruched side seams
- Maxi-length hem, curve-hugging fit
- Runs true to size
Style Number/Barcode: 05102-6056

Category Name: Casual Dresses

Price: $9.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free

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