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.
Now Trending
STYLE SPOTLIGHT
Discover New Skater Dress Styles
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!
-
Sunset Happy Hour Ruffled Skater Dress
This skater dress was made for sunset happy hours this season! It features a sleeveless V-neckline, halter tie-back straps, an open back, a stretchy smocked high waist, a short skater skirt with a tiered ruffled design, and a fit and flare silhouette. The lightweight twill fabric includes a woven lining. Style this short dress with espadrille sandals and a mini handbag.
Fit & Features
- Sleeveless V-neckline
- Halter tie-back straps, open back
- Stretchy smocked high waist
- Short skater skirt, tiered ruffled design
- Fit and flare silhouette
- Twill fabric, woven lining
- Runs true to size
Style Number/Barcode: 05102-000575
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE-3
Available Size: XXS, XS, S, M, L
-
Lace Me Up Denim Mini Dress
Denim but make it daring. This lace-up halter mini brings that effortlessly cool, slightly rebellious vibe—perfect for nights when you’re feeling bold and unstoppable.
Fit & Features
- Vintage-inspired denim fabric
- Halter plunge neckline
- Lace-up front bust design
- Stretchy smocked back panel
- Contouring seam detailing
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000288
Category Name: Casual Dresses
Price: $23.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Curve Flow Bodycon Midi Dress
Sleek, soft, and made to flatter. This mock neck midi dress hugs in all the right places with side ruching and a soft modal blend knit fabric that gives casual polish. Perfect for weekday styling and weekend looks!
Fit & Features
- Soft modal-blend knit fabric, knit lining, moderate stretch
- Sleeveless mock neck
- Side ruched seams
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000287
Category Name: Casual Dresses
Price: $42.90
Availability: Out of Stock
Product Badge:- Ships Free
-
Twirl Agenda Chiffon Mini Dress
Romantic with a little edge, this chiffon mini is made to move. The halter neckline, lace-up corset detailing, and tiered ruffles bring that flirty, fairytale energy—perfect for brunch to concerts, and daydreaming.
Fit & Features
- Chiffon fabric, stretchy knit lining
- Halter V-neckline, tie closure
- Dual front lace-up plackets
- Corset-inspired fitted bodice
- Drop waist seam
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000293
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M
-
Always Effortless Halter Bodycon Mini Dress
From brunch to dinner date plans, this halter bodycon mini dress will always collect compliments!
Fit & Features
- Mesh fabric, stretchy knit lining
- Halter sweetheart neckline, tie closure, padded bra cups
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05103-5847
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: YELLOW, SAGE, WHITE
Available Size: S, XS, M
Product Badge:- Sale
-
Out Of Office Abstract Maxi Dress
Booked, busy, and dressed for it. This abstract mesh strapless tube maxi dress hugs your curves with a sleek fit and side slit that brings just enough drama for vacations and sunset dinners with a view.
Fit & Features
- Abstract print, knit fabric
- Strapless neckline
- High side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000305
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
-
Lover’s Lane Lace Mini Dress
Soft romance meets modern elegance. This long sleeve mini dress stuns with a floral-pattern lace overlay, flirty tiered ruffle skirt, and open tie-back detail that feels effortlessly chic from every angle. Perfect for bridal celebrations, brunch, or dressy parties.
Fit & Features
- Floral pattern lace overlay, stretchy knit lining
- Boat neckline
- Sheer fitted long sleeves
- Open tie-back design
- Form-hugging fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000311
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirt Frequency Ruffle Dress
She’s got depth and a little drama. This abstract mesh mini dress features a plunging V-neckline, ruched bodice, and tiered ruffle hem that moves with every step—aka, the perfect mix of flirty and effortless.
Fit & Features
- Abstract print, mesh-lined stretch fabric
- Plunge V-neckline
- Twisted shoulder straps
- Open back detail
- Form-hugging fit
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000313
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M
-
Ocean Bloom Halter Mini Dress
Meet your next weekend obsession. This floral halter mini dress brings vacation energy anywhere you wear it, with its draped halter cowl neckline, open tie back, and flowy fit. Perfect for rooftop brunches, date nights, or celebrations.
Fit & Features
- Floral print, colored rhinestone embellishments
- Chiffon fabric lined with chiffon
- Cowl halter neckline
- Dual open tie-back design
- Side zipper and hook-eye closure
- A-line fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000316
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BLUE
Available Size: XS
-
Caught In The Wild Leopard Mini Dress
Go wild with it. This leopard mesh mini dress serves flirty movement and fierce energy with its ruched bodice, tiered skirt, and curve-hugging fit that’s made to stand out.
Fit & Features
- Sheer leopard mesh fabric with stretch lining
- V-neckline
- Spaghetti straps
- Fitted bodice with ruched detailing
- Tiered ruffle skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000318
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Fierce And Refined Leopard Cowl Maxi Dress
Fierce meets refined with this leopard maxi dress made to command attention. Designed with a plunge cowl neckline and a daring high slit, it turns every step into a moment- finished with an open back and sleek hoop that makes it unforgettable from every angle.
Fit & Features
- Leopard print, mesh-lined fabric, moderate stretch
- Plunge cowl neckline, tie closure
- Open back with hoop insert
- High front slit
- Curve-hugging silhouette, maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000319
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Daydream Drama Polka Dot Satin Mini Dress
A flirty mix of sweet and sultry, this satin mini brings the playful allure. The lace trim and open lace-up back make it a total show-stealer—perfect for brunch dates, parties, or spontaneous plans that somehow turn into the best stories.
Fit & Features
- Polka dot print, silky satin fabric, chiffon lining, no stretch
- Lace trim V-neckline
- Spaghetti straps
- Lace-up open back, hidden lower back zipper with hook-eye closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000507
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: IVORY, PINK
Available Size: S, L, XS, M
-
Midnight Ember Mesh Mini Dress
Hot from every angle. This abstract mesh mini dress features an asymmetrical neckline, ruched sides, and a curve-hugging fit that brings the drama. Sheer sleeves and smoky tones make it perfect for nights that start with dinner and end at sunrise.
Fit & Features
- Abstract print mesh-lined fabric, moderate stretch
- Asymmetrical one-shoulder neckline
- Sheer fitted long sleeves
- Side cutout waist
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000328
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Retro Romance Halter Midi Dress
Flirty, fitted, and effortlessly classic. This halter midi dress features a plunging neckline and all-over polka dot print for that perfect mix of vintage charm and modern polish. Perfect for brunch, celebrations, or date night!
Fit & Features
- Polka dot print, mesh-lined fabric, moderate stretch
- Halter V-neckline
- Curve-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000327
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLACK
Available Size: L
-
Wild Heat Halter Mini Dress
For when you want to look effortlessly wild. This halter mini dress blends sultry animal-inspired mesh with a flowy handkerchief hem—made for twirling, flirting, and maybe a little trouble.
Fit & Features
- Abstract animal print, mesh-lined fabric, moderate stretch
- Halter V-neckline, tie closure, hardware insert
- open back
- Fitted bodice
- Flowy handkerchief mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000329
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Effortless Aura Long Sleeve Midi Dress
Minimal effort, maximum effect. This off-the-shoulder ribbed midi dress hugs in all the right places with a soft stretch knit that’s made for cozy-chic moments. Style it with gold hoops and strappy heels for that quiet luxury vibe.
Fit & Features
- Soft rib knit fabric, sewn-in knit lining, moderate stretch
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Center back slit
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000331
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Afterlight Abstract Midi Dress
Turn up the heat in this sleek mesh halter midi. Designed with a scoop halter neckline, open back, and figure-hugging silhouette, this dress is the kind that makes a subtle entrance and leaves a lasting impression.
Fit & Features
- Abstract print, mesh-lined stretchy fabric
- Scoop halter neckline, tie closure
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000332
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: In Stock
Available Color: RED
Available Size: XS
Product Badge:- Sale
-
Effortless Cutie Off-The-Shoulder Mini Dress
Your “cute but effortless” mini dress has entered the chat. The off-the-shoulder neckline and body-hugging ribbed knit bring soft confidence with a flirty edge—made for everything from coffee dates to late-night plans.
Fit & Features
- Ribbed knit fabric, high stretch
- Sweetheart neckline, knot accent at the bust
- Off-the-shoulder design
- Long fitted sleeves
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000334
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Effortlessly Bold Abstract Print Halter Mini Dress
Soft drama with a daring edge. This abstract print halter mini dress hugs where it counts and moves like it knows you’ve got plans—perfect for nights out, birthday 'fits, and anytime subtle just isn’t the goal.
Fit & Features
- Sheer mesh fabric with brushed knit lining, high stretch
- Abstract print
- Sleeveless plunging V-neckline, bar strap with beaded accents
- Tie-back halter straps, open back
- Drop waist design, ruched detailing
- Tiered ruffled design, mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000326
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Refined Chic Ribbed Midi Dress
Simple, sleek, and seriously versatile. This ribbed midi dress nails that effortlessly polished vibe with a body-hugging fit and mock neckline. Style with gold hoops and slides for brunch—or heels and a blazer for a polished look for a business lunch.
Fit & Features
- Soft rib knit stretch fabric, knit lining
- Sleeveless mock neckline
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000337
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Denim Daze Sparkle Mini Dress
Denim, but make it extra. This strapless mini dress brings the shine with allover sparkle and a sculpted fit that’s ready for day or night out plans.
Fit & Features
- Denim fabric with faux pearl and rhinestones
- Strapless neckline
- Back zipper and hook-eye closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000339
Category Name: Casual Dresses
Price: $62.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M
-
Minimal Drama Off-The-Shoulder Midi Dress
Simple, sleek, and seriously flattering. This foldover off-the-shoulder midi dress hugs every curve with a soft stretch fit—perfect for dinner plans, date nights, or any moment that calls for subtle confidence.
Fit & Features
- Brushed knit fabric, smooth stretchy knit lining
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000340
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Always Out Animal Open Back Maxi Dress
Walk in, and suddenly everyone’s paying attention. This cowl neck maxi dress drapes effortlessly with a bold print, open back, and high slit that was made for cocktail hour.
Fit & Features
- Animal print, mesh-lined stretchy fabric
- Cowl halter neckline, tie straps
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000342
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
-
Retro Chic Vibes Halter Polka Dot Mini Dress
You + this polka dot dress = the cutest throwback moment. The halter neckline and open back bring the drama, while the drop waist silhouette adds that flirty, vintage flair.
Fit & Features
- Silky smooth satin fabric with polka dot print, woven lining
- Halter neckline with tie-back
- Open back design, lower zipper and hook-eye closure
- Pleated drop waist with mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000341
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free