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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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!
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Simply Chic A-Line Smocked Dress
Keep it simply chic with a dress that says it all!
Fit & Features
- Elastic Square Neckline
- Tie Front Accent
- Long Sleeve | Elastic Cuffs
- Smocked Waist
- A-Line Silhouette
- Lined Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0465
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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