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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Floral The Right Reasons High Neck
Brunch? Wedding guest? Winery? This floral mini dress is perfect for all these special occasions!
Fits & Features
- Adjustable Spaghetti Straps
- Lace Zipper Back
- High Neckline
- Mini Length Silhouette | Skater Skirt
- Smooth Scuba Fabric With Floral Prints
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05101-0168
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Radiating Ruffles Chiffon Dress
Glow up in this pretty ruffle dress, perfect for brunch with the squad! Pair this airy dress with cute wedges and dainty accessories for a head-turning look!
Fit & Features
- Wrap V Neckline
- Long Bishop Sleeves | Single Button Closure Cuff
- Tie- Waist Belt
- Tiered Ruffle Silhouette
- Lined Chiffon Fabric
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0510
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Petal Perfection Cowl Neck Midi Dress
Charm them all in this pretty midi dress! Soft watercolored petals and a trendy cowl neckline make a romantic combination for this wedding guest dress!
Fits & Features
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Spaghetti Straps That Cross At The Back
- Cowl Neckline
- Midi Length Silhouette
- Stretchy Floral Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0662
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Spaghetti Straps That Cross At The Back
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My Wavelength Skater Mini Dress
Good vibes only in this skater dress! The mini skater dress features a deep v-neckline, spaghetti straps that offer plenty of support, back zip, a darted bust that adds structure to the bodice, a banded waist that flatters, and A-line flared skirt. Complete outfit with chic clear heels and statement earrings.
Fit & Features
- Sleeveless v-neckline
- Darted seams at the bust
- Spaghetti straps
- Banded waist
- A-line skater silhouette
- Composed of soft mid-weight woven fabric
- Form hugging fit
Ivory and Mint Dress: Model is 5'8" with a 34" bust, 25" waist and 34" hips. She is wearing a size small.
Blue Dress: Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Denim Dress: Model is 5'8" with 32" bust, 24" waist and 36.5" hips. She is wearing a size small.
Style Number/Barcode: 05101-8697
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Budding Love Floral Mini Dress
Show your love for florals in this pretty mini dress! It's the prettiest pick for a wedding guest look!
Fits & Features
- Adjustable Spaghetti Straps
- Sweetheart Neckline I No-Slip Interior Strip
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Lined, Smooth Scuba Fabric With Floral Prints Throughout
- Curve Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0007
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Wild Bloom Mesh Maxi Dress
Serving fierce meets floral—this mesh maxi dress is pure goddess energy. Perfect for a sunset dinner on vacay or a chic cocktail bar.
Fit & Features
- Leopard, floral printed mesh-lined fabric
- V-neckline, wide shoulder straps
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000296
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Felt Cute Button Off Shoulder Mini Dress
Felt cute, probably leaving on! Show off those curves in this sweet mini! Opt for some strappy mules and a pair of chic earrings for an adorable attire!
Fits & Features
- Off Shoulder Design I Short Sleeves
- V Neckline
- Snap Button-Front
- Ribbed Knit Fabric
- Mini Length Hem
- Figure Hugging I Plenty Of Stretch
Style Number/Barcode: 06005-0636
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blossom And Bloom Square Neck Skater Dress
Show that springtime glow in this skater dress! Twirl 'round and 'round and capture everyone's attention with the gorge floral prints!
Fits & Features
- Spaghetti Straps
- Square Neckline With Center Tie Front
- Mini Length Hem I Skater Style Silhouette
- Smooth Knit Fabric I Floral Print Design
Model is 5'7" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0417
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sassy Stripes Midi Dress
We're feeling sassy in stylish stripes! Take on the season in this chic midi dress, perfect for your next brunch! Pair this piece with wedges and dainty accessories for a complete look!
Fit & Features
- Scoop Neckline
- Spaghetti Straps
- Cros-Back Straps
- Multi-Stripe Pattern
- Midi Length Silhouette
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0658
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Allure Them All Scoop Neck Tank Midi Dress
Allure them in this knockout sweater midi dress! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a scoop neckline, tank-like straps, and a midi-length silhouette. Elevate your look with square toe strappy mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
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Tank shoulder straps
- Scoop neckline and back
- Midi-length hem
- Ribbed sweater-knit fabric
- Plenty of stretch
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-0604
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tank shoulder straps
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Floral Chiffon High Low Dress
We're head over heels in love with fab florals! Bring the charm with this pretty high low dress! Pair with a statement heel and neutrals for a soft glam look!
Fit & Features
- V-Neckline | Spaghetti Straps
- Floral Lace Back | Open Lower Back
- Floral Print
- Lined Chiffon Fabric
- High Low Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05101-0314
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flaunt Those Florals Waist Tie Dress
Work that springtime magic in this pretty and sweet maxi dress! Add a woven bag and wedges for a completed look!
Fits & Features
- Plunging V Neckline
- Waist Tie Design
- Sleeveless Bodice
- Maxi Length Silhouette
- Woven Fabric I Ditsy Floral Print Design
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05102-0739
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Own The Night Mini Dress
Own the night with this chic little mini dress! Pair this head-turner with strappy stilettos and an envelope clutch for a classy night out with the squad bby!
Fit & Features
- V-Neckline
- Double Row of Spaghetti Straps
- Cross-Back Straps
- Mini Length Silhouette
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05103-0762
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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You're The One Bodycon Midi Dress
There's truly no one like you bb girl! With a statement single strap and a figure-hugging fit, you'll be feeling fierce in this basic ribbed dress!
Fits & Features
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One Shoulder Strap
- Slanted Neckline
- Midi Length Hem
- Ribbed Knit Fabric
- Figure Hugging I Moderate Stretch
Style Number/Barcode: 05102-0685
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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One Shoulder Strap
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On My Level Ruched Mini Dress
GIRLLL, they'll want to get on your level as soon as they see you in this! Slip into some pumps to really elevate your look!
Fits & Features
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Elastic Spaghetti Straps
- Scoop Neckline
- Mini Length Silhouette
- Ruching All Over
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0661
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elastic Spaghetti Straps
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Petit Blooms Floral Eyelet Midi Dress
Dainty floral makes this eyelet midi dress the cutest spring-to-summer style!
Fit & Features
- Dainty floral print, eyelet fabric, sewn-in knit lining
- Strapless neckline
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-6043
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Romantic Blooms Floral Chiffon Wrap Mini Dress
Cupid's got us struck! This romantic airy mini dress is perf for that daytime date you got lined up! Add block heels and a cute cross-body and you'll be all set bb!
Fits & Features
- Sheer Short Sleeves & Back
- Plunging V Neckline
- Tie Waist Wrap Design
- Mini Length Silhouette
- Chiffon Fabric I Fully Lined I Floral Print
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0796
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Thing Chiffon Wrap Mini Dress
Charm them all, sweet thangggg! They'll be enamored by you in this cute mini dress! Dress up by wearing block heels and adding a cute mini purse!
Fits & Features
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Sheer Flutter Sleeves & Back
- Plunging V Neckline
- Tie Waist Wrap Design I Belt Loops At Back
- Mini Length I Overlap Ruffle-Trim Hem
- Chiffon Fabric I Lined
- Relax Fit I Minimal Stretch
Style Number/Barcode: 05101-0798
Category Name: Casual Dresses
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sheer Flutter Sleeves & Back
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Swoon Worthy Off Shoulder Mini Dress
Walk right in and watch them swoon all over you in this bodycon mini! Dress it up with some heels and a mini purse to match!
Fits & Features
- Off Shoulder Design & Straps
- Mini Length
- Curved Hemline
- Textured Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0747
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Little Bit Of Drama Puff Sleeve Mini Dress
A streamlined LBD with a little bit of drama. Adds some strappy heels and gold-tone jewelry for an eyecatching look!
Fits & Features
- Square Neckline
- Sheer Dobby Mesh Puff Short Sleeves
- Mini Length Silhouette
- Crepe Fabric
- Form Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0734
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle Detail Eyelet Off The Shoulder Mini Dress
Ruffle up your gorg look with this effortless eyelet detail mini dress! Pair with some gold hoops and strappy mules for an everyday style you'll love!
Fit & Features
- Off the shoulder square neckline
- Short ruffle sleeves
- Ruffle overlay
- Center ruffle detail
- High waist
- Short ruffle hem
- Eyelet detail woven fabric
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0764
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Blissful Cutie Halter Cutout Skater Dress
Get swept off your feet in this cute skater dress for any casual occasion! With its halter neckline and cutout bodice, this dress is designed to show off your figure, while the ruffled mini-length hem adds a flirty touch.
Fit & Features
- Gauze woven fabric, woven lining
- Halter neckline with spaghetti strap ties
- Stretchy smocked bust
- Cutout bodice
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-6017
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take On The Night Chiffon Smocked Mini Dress
We'd love to see you take on the night in this, gorgeous! Just slip into some strappy heels to really elevate your lewk!
Fits & Features
- Surplice V Neckline
- Sheer Long Sleeves
- Smocking At The Cuffs & Skirt
- Cut Out At Back With Button Closure
- Mini Length Silhouette I Ruffle Trim Hem
- Chiffon Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0810
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Polka Dot Sweetheart Mesh Mini Dress
You'll be totally sweet on this adorable polka dot mesh LBD! Pair with some sneaks and a jean jacket to give it a spring time vibe!
Fit & Features
- Short puff sleeves | Ruffle trim
- Wrap front sweeheart neckline
- Sheer mesh waist panel and back
- Short, form hugging fit
- Sheer polka dot mesh fabric | Knit lining
- Moderate stretch
Style Number/Barcode: 05102-0608
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance