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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Dreamy In Florals Tie Front Mini Dress
Bring the spring vibes in this cute and dreamy mini dress! We'd love to see you styling this with a pair of white sneakers or chunky heels!
Fits & Features
- Spaghetti Straps
- Plunging V Neckline I Bust Tie With Keyhole Opening I Square Back
- Mini Length Silhouette
- Textured Knit Fabric I Ditsy Floral Print
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05101-0442
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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:- Clearance
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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:- Clearance
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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:- Clearance
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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
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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
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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
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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
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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
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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:- Clearance
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Spaghetti Straps
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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
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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
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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
Style Number/Barcode: 05102-0471
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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
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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
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Elastic, Strapless Neckline
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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
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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
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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
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Adjustable Spaghetti Straps
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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
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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
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Spaghetti Straps
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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
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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
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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
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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
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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
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Adjustable Spaghetti Straps
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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
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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
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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
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Adjustable Spaghetti Straps
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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
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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
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Short, Puff Sleeves
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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
- Dual Off Shoulder Bar Straps