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.

Babe In Denim Mini Dress
Made for a babe like you! Stow away those jeans and rock this denim mini dress. For chillier days, pair it with a long sleeve tee and some matching sneakers!

Fits & Features
- Adjustable Spaghetti Straps
- Sweetheart Neckline
- Linear Seams & Stitching Down Front
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Denim Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0740

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Sweetest Look Floral Off Shoulder High Low Skater Dress
Enchant everyone with the sweetest of looks! Look flowy and fresh in this captivating dress. Complement your attire with cute earrings and a pair of clear strap mules!

Fits & Features
- Off Shoulder Neckline & Sleeves
- Subtle High Low Hem I Skater Silhouette
- Smooth Scuba Fabric I Floral Print
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0142

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Breezy Babe Crochet Maxi Dress
Enchant them all in this maxi dress! It's the perf vacay dress you need to pack before that trip!

Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Lined Crochet Front Design
- Tie Open Back
- Flowy Maxi Length Silhouette
- Textured Knit Fabric I Partial, Mini Length Knit Lining
- Relaxed Fit I Moderate Stretch
Style Number/Barcode: 05102-0294

Category Name: Casual Dresses

Price: $19.97 $49.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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At First Sight Ponte Skater Dress
They'll be falling for you in this twirl-worthy skater dress! Slip into a pair of white sneakers for a charming daytime look and swap them out for block heels just in time for date night!

Fits & Features
- Dual Spaghetti Straps
- Strappy Cross Back Design
- Plunging V Neckline
- Mini Length Hem I Skater Silhouette
- Ponte Fabric
- Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0726

Category Name: Casual Dresses

Price: $9.97 $37.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sunkissed and Stunned Halter Striped Maxi Dress
This striped knit maxi brings the heat with a flirty open back, high front slit, and sheer vibes made for beach strolls or rooftop sips.

Fit & Features
- Striped texture knit design, sheer fabric
- Halter plunge neckline, tie straps
- Open back with tie strap
- High front slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000137

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Spring Simplicity Swiss Dot Babydoll Mini Dress
Charm them all with this sweet and simple babydoll dress! Put your hair in a cute updo and slip into some block heels for a fabulous spring look!

Fits & Features
- Scoop Neckline
- Ruffles At Sleeve Openings
- Keyhole Opening At The Back I Button Closure
- Mini Length Hemline
- Swiss Dot Woven Fabric I Fully Lined I Round Eyelet Design At The Top Front & Along Skirt
- Relaxed Fit I Minimal Stretch
Style Number/Barcode: 05102-0731

Category Name: Casual Dresses

Price: $9.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stylish In Stripes Tassel Waist Tie Mini Dress
Leave work looking absolutely stylish in stripes with this cute mini dress! You'll love the cute drawstring tassels that cinch your waist! Slip into a pair of block heels and get your hair up into a high pony for a chic look!

Fits & Features
- V Neckline
- Button-Front
- Drawstring Waist With Tassel Detail
- Mini Length, Ruffle-Trim Hemline
- Drop Shoulder Balloon Sleeves With Elastic Cuffs
- Woven Fabric With All Over Striped Print
- Relax I Minimal Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0732

Category Name: Casual Dresses

Price: $17.97 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Got A Flair For It Ruffle Hem Mini Dress
Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!

Fits & Features
- Spaghetti Straps
- Square Neckline I Princess Seams
- Back Zipper With Hook & Eye Closure
- Side Ruching
- Mini Length Silhouette I Ruffle Trim Hemline
- Smooth Textured Woven Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0698

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Sunset Dream Tie Dye Satin Midi Dress
You'll look like the perf sunset dream in this tie dye midi dess! Pair with some espadrille sandals for a stylish summer time vibe.

Fit & Features
- Tie shoulder spaghetti straps
- Cowl square neckline
- Flattering horiztonal seam under the bust
- Back bar detail | Partial open back
- Flowy mid-length hem
- Tie dye satin-like fabric | Sheer woven lining
Style Number/Barcode: 05102-0737

Category Name: Casual Dresses

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Pop Of Color Block Ditsy Floral Midi Dress
Give them a pop of color this season in this flowy dress! Add a pair of block heels and cute mini purse for an OOTD!

Fits & Features
- Tank Shoulder Straps
- Plunging V Neckline & Back
- Back Zipper With Hook & Eye Closure
- Midi Length I Overlapping Ruffle Trim Hem
- Woven Fabric With Ditsy Floral Print & Color Block Design I Partial, Mini Length Lining
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0809

Category Name: Casual Dresses

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Denim Diva Zip Front Mini Dress
Stow your jeans and bust out a denim mini dress for the spring szn! Pair this with a lightweight long sleeve and some cute ankle booties!

Fits & Features
- Tank Shoulder Straps
- Scoop Neckline & Back
- Zipper Front I Linear Seam Details
- Mini Length Silhouette
- Denim Composition
- Form Hugging Fit I Moderate Stretch
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0471

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Flower Up Strapless Skater Dress
Recharge your wardrobe by adding some bright floral prints! We know you'll be slaying it in the Flower Up skater dress.

Fits & Features
- Elastic, Strapless Neckline
- Mini Length Silhouette I Skater Style Skirt
- Chiffon Fabric I Floral Print All Over
- Ruffle-Trim At Hem & Neckline
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0418

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Body Language Tube Mini Dress
Warning: may cause jaw drops. With a sleek tube neckline and a sultry cutout, this bodycon mini dress is serving curvy drama all night long!

Fit & Features
- Soft knit stretchy fabric, smooth knit lining
- Strapless tube neckline
- Side cutout bodice, draped accent
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000226

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Can't Forget Me Floral Side Ruched Mini Dress
Honey, they can't even take their eyes off of you! Walk around like the goddess you are in this figure-hugging mini dress! Don't forget to add some heels to really pull th look together for that brunch you got planned

Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Square Back
- Mini Length Silhouette
- Ruching Along Side Seam
- Stretchy Woven Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0520

Category Name: Casual Dresses

Price: $9.97 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Got A Flair For It Ruffle Hem Mini Dress
Add some flair to your movement with this ruffle mini dress! Pair with some block heels and hoop earrings!

Fits & Features
- Spaghetti Straps
- Square Neckline I Princess Seams
- Back Zipper With Hook & Eye Closure
- Side Ruching
- Mini Length Silhouette I Ruffle Trim Hemline
- Smooth Textured Woven Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0697

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Dreamy Petals Off Shoulder Midi Dress
A picture-perf dress for that girls brunch! Wave your hair out and add some gold-tone jewelry for a spring-ready look!

Fits & Features
- Off Shoulder Neckline & Sleeves
- Midi Length Silhouette
- Smooth Scuba Knit Fabric I Watercolored Florals
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0661

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Floral Stunner Ruched Maxi Dress
You'll be quite the stunner in this floral ruched maxi dress! Its stretchy knit fabric will hug and flatter your curves beautifully!

Fit & Features
- Spaghetti straps | Cross back
- V neckline
- Center ruched detailing
- Front slit
- Stretchy knit fabric
- Floral print
Style Number/Barcode: 05101-0073

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Eyelet Puff Sleeves Mini Dress
Do a little spring cleaning with your wardrobe and add this charming mini dress to cart...you know it'll be part of your rotation! We love pairing this look with a denim jacket and some heels!

Fits & Features
- Elastic Puff Shoulder Short Sleeves I Can Be Worn Off Shoulder
- Square Neckline
- Mini Length Silhouette
- Textured Knit Fabric With Eyelet Design I Fully Lined
- Form Hugging Fit I Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0486

Category Name: Casual Dresses

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Picturesque Petals Tiered Ruffle Chiffon Mini Dress
Feel and look picture-perf in this fun floral dress! Pair your look with a denim jacket and some white sneakers!

Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Square Sheer Back
- Drawstring Waist
- Mini Length Silhouette I Tiered Ruffle Trim Design
- Floral Chiffon Fabric I Fully Lined
- Zipper Not Featured
Style Number/Barcode: 05102-0503

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Carmela Metallic Shine Party Dress
Special Occasion

You'll be leading the dance floor in our sparkling Carmela! Twist, twirl, and bust a move in her flowy skater skirt while showcasing all the shine from every angle. Style her up with some rhinestone heels and a pair of earrings to match!

Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust I Mesh Inset
- Mini Length Hem I Skater Silhouette
- Mesh Inset At Back With Triple Row Detail I Back Zipper With Hook & Eye Closure
- Mesh Lined Metallic Threaded Fabric I Fully Lined
- Form Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0417

Category Name: Casual Dresses

Price: $31.97 $69.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Crush On You Lace Bust Skater Dress
The lace bodice and flirty skater skirt are a few of the crush-worthy deets of this lovely dress!

Fits & Features
- Adjustable Spaghetti Straps
- Embroidered Lace Design At The Front Bodice I Lightly Padded
- Cut Out At Center Front Waist
- Mini Length Hem I Skater Style Skirt
- Crepe Fabric
- Back Zipper With Hook & Eye Closure
Style Number/Barcode: 05101-0517

Category Name: Casual Dresses

Price: $9.97 $41.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Square Neck Floral Mini Dress
Look as beautiful as a bouquet in this springtime dress! It's the perf brunch fit once you accessorize with some nude heels and earrings!

Fits & Features
- Short, Puff Sleeves
- Elasticized Square Neckline & Cuffs
- Smocked Bodice
- Mini Length Silhouette I A-Line Skirt
- Woven Gauze Composition I Floral Prints
- Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0493

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Give It A Spin Off Shoulder Pleated Skater Dress
Look chic and cute in this twirl-worthy skater dress! Her best features are def the hidden hand pockets Make sure you get a pair of block heels to complement this dress!

Fits & Features
- Dual Off Shoulder Bar Straps
- V Neckline I Elastic Square Back
- Hidden Hand Pockets
- Mini Length Silhouette I Pleated Skirt I Skater Silhouette
- Crepe Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0783

Category Name: Casual Dresses

Price: $9.97 $38.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sweet & Smocked Ditsy Ruffle Midi Dress
Get into the spring vibe with this midi dress on! Easily style it up or down by switching out your white sneakers to heels!

Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline
- Tiered Ruffle Detail
- Midi Length Silhouette
- Ditsy Woven Print
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0501

Category Name: Casual Dresses

Price: $18.97 $46.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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