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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Sweet Like Sugar Gingham Print Skater Dress
This gingham skater dress is all flounce and flirt, from the dainty bow detail to the ruffled puff sleeves—perfect for farmers' market strolls, daydreams, and twirling through your soft girl era.
Fit & Features
- Cotton-blend woven fabric
- Gingham print
- V-neckline with small bow detail, short puff sleeves, ruffled trim
- Stretchy smocked bodice
- High-rise waist seam
- Short pleated skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000139
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Edge of Allure Cutout Mini Dress
The kind of dress that doesn’t wait for an occasion. This one-shoulder mini dress hugs your curves with asymmetric ruching and a daring side cutout—perfect for owning the night (and every entrance).
Fit & Features
- Smooth knit stretchy fabric
- One-shoulder neckline
- Side cutout waist accent
- Bodycon fit
- Asymmetrical mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000239
Category Name: Casual Dresses
Price: $21.00 $29.90
On Sale: Yes
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
Product Badge:- Sale
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Autumn Attitude Strapless Pleated Plaid Mini Dress
Embrace the new season in this plaid mini dress featuring a strapless neckline, form-hugging silhouette, and a flirty pleated mini-length hem. Perfect for back-to-school and styling with flats.
Fit & Features
- Plaid pattern, knit fabric, moderate stretch
- Strapless folded neckline
- Form-hugging silhouette
- Pleated mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5863
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Blue Crush Denim Halter Skater Dress
Meet your new denim obsession. This square neck halter mini dress serves curve-hugging confidence with belted detailing and flirty side cutouts made for catching glances.
Fit & Features
- Stretch denim fabric, knit panty lining
- Adjustable belted halter square neckline, foldover accent
- Back zipper and hook-eye closure
- Side waist cutouts
- Front seam detailing
- Skater short-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000241
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Alluring Sensation Halter Open Back Maxi Dress
Wherever your summer takes you, this maxi dress will look sensational against any tropical or beach background! This dress features a striking cowl halter neckline, a sleek hoop insert, and a captivating form-hugging silhouette, while the open back adds a daring touch.
Fit & Features
- Slinky knit stretchy fabric
- Cowl halter neckline, hoop insert, tie back
- Open back
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000124
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Bound Lace-Up Print A-Line Dress
With an Italian-inspired print, this A-line dress is perfect for packing with you! This dress is designed in a flattering A-line mini silhouette with a stylish lace-up front and a chic cutout back that turns heads.
Fit & Features
- Multi-printed, woven fabric, woven lining
- V-neckline with lace-up bust
- Adjustable spaghetti straps
- Cutout back
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000150
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Thriving Blooms Corset Floral Slit Midi Dress
Thrive with sweet energy in this floral midi dress perfect for brunches or dates! With a corset bodice that snatches your waist and a flirty front slit, this a-line dress will captive everyone. Pair with a necklace.
Fit & Features
- Ditsy floral print, woven fabric
- Wide shoulder straps, sweetheart neckline
- Corset bodice
- Side pockets
- A-line silhouette, front slit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-4051
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sun And Spritz Tropical Cutout Maxi Dress
Just add sun and a spritz—this tropical print maxi is made for main character getaways. With side cutouts and breezy vibes, it’s giving effortlessly hot in every snap.
Fit & Features
- Lightweight woven fabric with tropical print, bust lining
- Square neck
- Cutout sides on the bodice
- Fitted bodice with trim detailing
- Bust tie, tank shoulder straps, back zipper and hook-eye closure
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000246
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Elevated Edge Denim Corset Midi Dress
Effortlessly sculpted with just the right edge. This denim corset midi dress defines your shape with a structured bodice and a sleek strapless neckline that feels elevated, confident, and ready for plans that don’t end early.
Fit & Features
- Strapless sweetheart neckline
- Corset-inspired bodice with seamed detailing
- Back zipper and hook-eye closure
- Back slit for ease of movement
- Midi-length silhouette, bodycon silhouette
- Denim fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 05102-000250
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S
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Sweetheart Strings Lace-Up Denim Dress
This lace-up skater dress brings the perfect mix of sweet-meets-spicy with its sweetheart neckline, flirty pleated skirt, and strappy open-back moment that’s basically engineered for compliments.
Fit & Features
- Dark wash denim fabric
- Sweetheart neckline with front lace-up detail, grommet insets
- Adjustable spaghetti straps
- Open crisscross lace-up back
- Fitted bodice with pleated skater skirt
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000248
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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Flattering Look A-Line Ruffled Mini Dress
This A-line mini dress gives you a flattering look for every social event on your calendar! The V-neckline adds a touch of elegance to this fun, versatile piece. Perfect for a variety of occasions, this dress will keep you looking stylish. Complete the look with dainty earrings.
Fit & Features
- Soft model-blend knit fabric, lined, moderate stretch
- V-neckline
- A-Line silhouette
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5769
Category Name: Casual Dresses
Price: $7.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Time To Vacay Halter Lace-Up Maxi Dress
Your next vacay fit is here - say aloha to this knit maxi dress designed to showcase your curves in a bodycon fit and bare some skin with the alluring lace-up back.
Fit & Features
- Texture knit fabric, knit lining, moderate stretch
- High halter neckline
- Spaghetti straps
- Lace-up back
- Bodycon fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000053
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rustic Charm Faux Suede A-Line Mini Dress
Channel all the cozy fall feels with a sleek twist. This faux suede mini dress features a button-front design and a daring open back, accented by a statement buckle strap. Perfect for layering under a trench or pairing with knee-high boots for an effortlessly chic allure.
Fit & Features
- Smooth faux suede fabric, sewn-in knit lining
- Sleeveless crew neck
- Adjustable buckle strap and cutout design
- Front button accents
- A-line fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000258
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Days Floral Halter Skater Dress
Sunny days call for this cute floral skater dress featuring tie-back straps and a breezy fit-and-flare silhouette!
Fit & Features
- Rayon woven fabric
- Floral print
- Sleeveless V-neckline
- Tie-back halter straps
- Open back, lower tie-back design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5874
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Spell Lace Skater Dress
Flirty with a touch of vintage romance. This lace corset mini flatters every curve with a sweetheart neckline and flared skater skirt—made for date nights, parties, or whenever you want all eyes on you.
Fit & Features
- Lace-lined fabric, flocked velvet trims, attached panty lining
- Strapless sweetheart neckline, bust lining
- Corset-inspired sheer bodice, flexible boning
- Back zipper and hook-eye closure
- Ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000263
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Garden Party Chic Lace Floral Maxi Dress
Giving flirty fairytale but make it chic. This lace-trimmed maxi dress hugs like a dream and serves up soft-girl glam with a sultry high side slit. Perfect for garden parties, shower celebrations, and dressy dates.
Fit & Features
- Floral print, mesh-lined fabric
- Lace sweetheart neckline and shoulder straps
- Back zipper closure
- High side slit
- Form-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000264
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Spice Things Up V-Neck Cutout Skater Dress
Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- V-Neckline front and back
- Cutout bodice, elasticized straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5419
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Drama Edit Ruffle Mini Dress
Turn the charm all the way up in this halter mini dress that serves effortless allure. Designed with a flirty open back and tiered ruffle hem, it’s your go-to for nights that deserve a little drama.
Fit & Features
- Stretchy knit fabric
- Cowl halter neckline
- Open tie back
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000270
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced In Denim Strapless Mini Dress
Meet the denim moment everyone’s talking about. This strapless corset mini cinches you in all the right places with lace-up sides and a structured bodice that gives instant shape. It’s flirty, bold, and begging to be admired at concerts or nights out.
Fit & Features
- Denim fabric with slight stretch
- Strapless neckline
- Corset-seamed bodice, back zipper and hook-eye closure
- Rhinestone-embellished lace-up side plackets
- Curved drop waist seam
- Skater silhouette, frayed edge trim, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000273
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Game Set Slay Sweater Dress
She’s giving preppy with a playful twist. This sleeveless sweater dress hugs in all the right places with contrast trim and a flared mini-length hem that makes it a serve for every season!
Fit & Features
- Rib knit stretchy fabric
- Square neckline and tank shoulder straps, contrast trim
- Skater silhouette
- Pleated, flare mini-length hem
- Runs true to size
Style Number/Barcode: 06005-2219
Category Name: Casual Dresses
Price: $21.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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After Hours Pinstripe Lace Mini Dress
When the city lights come on, this dress takes over. The after-hours pinstripe lace mini serves sultry vibes with its corset fit, lace peekaboo, and flirty ruffle hem that’s made for late-night adventures.
Fit & Features
- Woven knit fabrication
- Pinstripe pattern
- Sleeveless sweetheart neckline
- Sheer lace panel front detail
- Tiered ruffled hemline
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05102-000276
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Delightful Charm Halter A-Line Midi Dress
Step out looking delightful in this charming sleeveless midi dress for parties or showers! The halter pleated neckline and open back add a flirty touch, while the beaded tie waist cinches your waist for a flattering A-line silhouette. Complete the look with sunglasses and sandals!
Fit & Features
- Woven fabric, no stretch
- Halter pleated neckline
- Open back, zipper and hook-eye closure
- Beaded tie waist
- A-Line silhouette
- Runs true to size
Style Number/Barcode: 05102-5648
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Instinct Tie Back Maxi Dress
Romantic with a wild streak. This halter maxi dress mixes abstract rose and animal prints with a lace-trim bust and open tie back—perfect for day or night out plans.
Fit & Features
- Abstract animal rose print, mesh-lined fabric, moderate stretch
- Halter plunge neckline, tie closure
- Lace bust
- Open tie back design
- Curve-hugging silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000279
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Easy Elegance A-Line Maxi Dress
Chic, minimal, and made for any moment. This strapless maxi dress keeps it effortless with a fitted bodice and flowy skirt that moves with you—perfect for everything from beach strolls to brunch dates.
Fit & Features
- Smooth knit stretch fabric
- Strapless tube neckline
- Fitted bodice
- Side pockets
- A-line silhouette
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000281
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S