Casual Dresses
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.
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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.
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Crushin' It Ditsy Smocked Mini Dress
We are crushing over this adorable mini dress! Wear it off the shoulder for a more boho-feel.
Fits & Features
- Square Neckline I Can Be Worn Off The Shoulder
- Sheer, Chiffon Blouson Sleeves
- Smocked Cuffs & Bodice
- Mini Length Silhouette I Pleated, Flowy Chiffon Hem
- Woven Fabric With Knit Lining
- Ample Stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0605
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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V In The Midi Dress
You'll want to slip right into this cozy and sexy midi dress! Pair with some cute heels and a leather jacket for the perf finishing touches.
Fits & Features
- V Neckline & Back
- Long Fitted Sleeves
- Midi Length Silhouette
- Ribbed Knit Fabric
- Curve Hugging Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06005-0394
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Color Block Knit Mini Dress
Keep it chic in stand out color block! This mini dress is perf to pair with your fav booties or strappy heels to easily dress up or down!
Fit & Features
- Mock Neck
- Sleeveless
- Color Block Design
- Ribbed Knit Fabric
- Mini Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'4" with 32" bust, 23" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 06005-0432
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortless Beauty Floral Skater Dress
You're all about that effortless beauty look. This floral skater dress has a flowy feel and a beyond gorg print that is totally your vibe.
Fit & Features
- Adjustable spaghetti straps
- Back zipper closure
- High square neck
- High waist seam
- Flowy skater skirt
- Floral print
- Chiffon fabric | Lining
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05101-0382
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Square Neck Smocked Midi Dress
Show off your figure in this body-lovin' midi dress! Add a cute pair of heels to level up your 'fit.
Fits & Features
- Short Sleeves I Elastic Shoulders & Cuffs
- Square Neckline
- Tiered Ruffle Trim Along The Bodice & Skirt
- Midi Length Silhouette I Ruffle Hem
- Smocking All Over
- Woven Fabric
- Form Hugging Fit I Plenty Of Stretch
Model is 5'8" with a 32" bust, 26" waist and 38" hips. She is wearing a size small.
Style Number/Barcode: 05102-0597
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flared and Flirty Ponte Skater Dress
Keep it flared and flirty in this twirl-worthy skater dress! Perfectly pair this dress with a set of fab pumps to make a chic impression!
Fit & Features
- V-Neckline
- Spaghetti Straps | Cross-At-Back
- Princess Seams
- Skater Silhouette
- Ponte Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0740
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ditsy Floral Doll Ruffle Mini Dress
OMG adorbs
Add a denim jacket and some white sneakers for a cute af 'fit! Fits & Features
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Ruffle Shoulder Straps
- Square Neckline & Back
- Mini Length Silhouette
- Smooth Knit Fabric I Ditsy Floral Print
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0389
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Shoulder Straps
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Daydream Date Bow-Front Skater Dress
Giving total daydream vibes with a flirty twist. The bow-front detail and breezy skater silhouette make this short dress perfect for brunch, strolls, or spontaneous golden-hour photo ops.
Fit & Features
- Satin woven fabric, scenic print
- Sleeveless V-neckline, bow-front detail
- Adjustable spaghetti straps, smocked back
- High-rise waist
- Short skater silhouette, striped hem
- Runs true to size
Style Number/Barcode: 05102-000306
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Zara Scallop V High Low Dress
Special Occasion
Steal the show in our lovely Zara! Her high low hem adds a flirty little touch!
Fits & Features
- Adjustable Spaghetti Straps
- Scallop Trim V Neckline I Padded Bust
- Elastic Square Back With Zipper & Hook And Eye Closure
- High Low Hemline
- Crepe Fabric
- Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0868
Category Name: Casual Dresses
Price: $19.97 $72.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Leopard Mesh Mini Dress
Flaunt that trendy leopard print in this fierce mini dress!
Fits & Features
- Elastic Bungee Strap
- Square Neckline & Back
- Mini Length Silhouette I Gathering Detail At Side Seams
- Knit Lining With Leopard Printed Mesh Overlay
- Curve Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0425
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Love For Leopard Mesh Mini Dress
Let your wild side come through in this killer mini dress!
Fits & Features
- Adjustable Spaghetti Straps
- Square Neckline & Back
- Mini Length Silhouette I Ruching Along Sides & Center Back
- Leopard Print Throughout With Mesh Overlay I Smooth Knit Lining
- Curve Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0512
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Falling For It Ruffled Chiffon Leopard Print Dress
Have them all falling for you when you step out in this flirty chiffon ruffled mini dress! Easily style with a pair of black mules and sweet pearl hoops!
Fit & Features
- Ruffle trim mock neckline
- Long sleeves with a ruffled wrist
- Relaxed bodice
- Stretchy smocked waist line
- Tired ruffled skirt
- Mini hemline | Lined at the skirt
- Slip on fit | No closures
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0513
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Hear Meow-Out Leopard Midi Dress
Fiercely command a room with this bold mini dress! They'll be listening to every fashion tip you got
Fits & Features
- Adjustable Spaghetti Straps Cross At Back
- Cowl Neckline I Back Zip
- Midi Length Silhouette I Side Slit
- Woven Fabric I Leopard-Inspired Print
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0371
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Scoop Neck Floral Mesh Mini Dress
Look fine in florals and strut your stuff in this fab mini dress!
Fits & Features
- Elastic Bungee Cord Straps
- Scoop Neckline I Square Back
- Mini Length Silhouette I Gathering Detail At Low Side Seams
- Knit Lining With Floral Printed Mesh Overlay
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0469
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Just A Lil' Knit Mini Dress
Show just a lil' when you slip into this knit mini dress with a peep of sexy!
Fit & Features
- Crew neckline
- Long Sleeves
- Cut out detail above the bust
- Form fitting silhouette
- Ribbed knit material
- Moderate stretch | Form fitting silhouette
- Mini length hemline
Style Number/Barcode: 06005-0536
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plant One On Floral Maxi Dress
Flaunt your florals in this gorge maxi dress! It's the perfect dress for the winery or as a wedding guest!
Fits & Features
- Spaghetti Straps
- V-Neckline
- Maxi Length Silhouette With Gathering & Slit Detail At Side
- Smooth Jersey Knit Fabric I Floral Prints Throughout
- Curve Hugging Fit
- Ample Stretch
Style Number/Barcode: 05102-0251
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Zebra Front Slit Midi Dress
Make a bold first impression in this statement dress! Pair with your fave leather jacket and some heels for a cute OOTN!
Fits & Features
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Adjustable Spaghetti Straps
- V Neckline I Back Zip With Hook & Eye Closure
- Lined At The Bodice
- Midi Length Silhouette I Front Slit
- Woven Fabric I Zebra Print Throughout
- Relax Fit I No Stretch
Style Number/Barcode: 05102-0368
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Adjustable Spaghetti Straps
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Tie Front Long Sleeve Mini Dress
Accessories and thigh-high boots are the way to go with this essential mini dress!
Fits & Features
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Square Neckline & Back
- Long Sleeves With Elastic Detailing At The Cuffs & Shoulders
- Mini Length Silhouette
- Tie Front Detail Along Skirt
- Brushed Knit Fabric
- Ample Stretch
Style Number/Barcode: 05102-0374
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Square Neckline & Back
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Fawning Over Florals Mini Dress
We adore this floral mini! Pair this with your fav heels and purse, and you're all ready for date night!
Fits & Features
- Elastic Bungee Cord Straps
- Square Neckline & Back
- Mini Length Silhouette
- Mesh Lined Fabric With Ruching & Floral Prints Throughout
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05102-0490
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Scuba Lace Back Mini Dress
Look your freshest in this pretty dress!
Fits & Features
- Spaghetti Straps I Lace Back With Zipper
- Plunging V Neckline
- Mini Length Silhouette
- Scuba Fabric With All Over Floral Prints
- Curve Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0495
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cat Touch This Satin Leopard Mini Dress
You can look, but you can't touch. Slay it in this feisty mini dress!
Fits & Features
- Self Tie Spaghetti Straps
- Square Neckline & Back
- All Over Smocked Design
- Mini Length Silhouette
- Satin-Like Fabric
- Curve Hugging Fit I Ample Stretch
Style Number/Barcode: 05102-0492
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Long Sleeve Ribbed Mini Dress
It may be cold, but you're heating up in this ribbed mini dress!
Fits & Features
- Surplice V Neckline I V Back
- Fitted Long Sleeves
- Mini Length Silhouette
- Midweight Ribbed Knit Fabric
- Curve Hugging Fit I Moderate Stretch
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Ivory: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 06005-0361
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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She's A Vision Abstract Cowl Slit Maxi Dress
Make a statement and turn heads in this abstract maxi dress on vacation or at a chic pool party! The cowl neck, adorned with hoop trims, adds a touch of glamour, while the high side slit and maxi length hem elongate your silhouette and add a hint of allure.
Fit & Features
- Abstract print, stretchy knit fabric
- Cowl neckline with hoop trims, spaghetti strap
- Open strappy back
- High side slit, hoop insert
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-6084
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polly Formal High Slit Dress
Special OccasionBring the glamour in the ever so lovely Polly dress! She features a vibrant yellow hue, a sleeveless bodice, a plunging V neckline, padded cups, princess seams and adjustable narrow straps. Her slim fit bodice leads to an elongating sweeping floor length A-Line skirt that is accented with a high side slit to show off your heel game! She offers a form hugging fit with minimal stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05002-0089
Category Name: Casual Dresses
Price: $9.97 $89.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free