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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Daylight Darling Eyelet Dress
This dress feels like sunshine plans waiting to happen. A knit eyelet skater dress with a scoop neckline and tie-back detail that brings the flirty flair to every plan.
Fit & Features
- Eyelet knit fabric
- Scoop neckline
- Spaghetti straps
- Tie-back design
- Layered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000383
Category Name: Casual Dresses
Price: $48.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Best Seller
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Flirty Escape Paisley Floral Dress
Light, flowy, and a little flirty, the open tie-back moment on this floral paisley dress keeps things interesting from every angle. It’s giving easy confidence with just enough detail to make them look twice.
Fit & Features
- Paisley floral print fabric
- Halter V-neckline, tie straps
- Open tie-back design
- Flowy skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000384
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: OLIVE
Available Size: XS, S, M, L
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Bare It Bold Halter Mini Dress
This one doesn’t wait for an invite. A barely-there halter with bold cutouts and an O ring detail that knows exactly what it’s doing—made for warm destinations and sunset dinners.
Fit & Features
- Soft ribbed fabric with a slinky feel
- Triangle halter neckline with tie straps
- O ring center with waist cutout detail
- Mini-length skirt with ruffle hem
- Runs true to size
Style Number/Barcode: 05102-000389
Category Name: Casual Dresses
Price: $49.90
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Attraction Cowl Neck Maxi Dress
Serving curves with a side of attitude. This leopard print mesh cowl neck maxi dress drapes just right with an open back and hardware detail that makes every step feel a little extra.
Fit & Features
- Leopard print, mesh fabric, knit lining
- Plunge cowl neck halter neckline, hardware insert
- Open back
- Curve-hugging, maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000393
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L, XL
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Untamed Glam Mesh Maxi Dress
For nights when subtle just isn’t in your vocabulary, this mesh maxi dress delivers full-throttle confidence. The abstract animal print, plunging neckline, and hardware detail hit that perfect mix of daring and glam, while the bodycon fit keeps the silhouette sleek and unforgettable.
Fit & Features
- Abstract animal print, mesh fabric, short knit lining
- Plunging neckline with hardware detail
- Fitted long sleeves
- Bodycon maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000391
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS
Product Badge:- Sale
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Vacation Glow Floral Mesh Bodycon Mini Dress
Sun-kissed and ready to steal the scene, this floral mesh mini dress brings that radiant, vacation-glow confidence. The soft bodycon fit hugs just right, with a halter plunge neckline and a draped sash that make your arrival feel effortlessly iconic.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch, large floral print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched waist, asymmetric metal hardware accent
- Ruffled side sash
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000392
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Can’t Resist Off-The-Shoulder Mini Dress
A little cozy, a little flirty—this rib knit mini dress does both. Designed with a foldover off-the-shoulder neckline, ruched sides, and a soft front drape that flatters every curve, it’s your go-to for coffee dates, casual dinners, or weekend chic plans.
Fit & Features
- Soft rib knit fabric lined with stretch knit
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Side ruched seams
- Front drape accent, bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000396
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet And Snug Cable Knit Mini Dress
Cozy meets curve-hugging. This cable knit mini brings that soft, flirty energy with a foldover off-the-shoulder neckline and bell sleeves for extra charm. Perfect for date nights in or dressing up your coffee run fit.
Fit & Features
- Soft cable knit fabric, stretch knit lining
- Foldover off-the-shoulder neckline
- Long bell sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000395
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Focus Moment Ribbed Knit Midi Dress
Soft curves, no effort. This ribbed knit midi dress hugs just right with a bodycon fit that moves from dinner plans to late-night photos without missing a beat.
Fit & Features
- Soft rib knit fabric, sewn-in stretch lining
- Sweetheart neckline with twisted bust detail
- Spaghetti straps
- Fitted bodice through the waist
- Bodycon silhouette through the hips
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000397
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Wild Bloom Cowl Halter Maxi Dress
Bold print, barely-there feel perfect for vacations. This maxi dress blends leopard and tropical florals with a plunging cowl halter and open back, finished with a statement floral hardware that stands out.
Fit & Features
- Tropical floral and leopard print
- Sheer mesh fabric, soft knit short lining
- Plunge cowl halter neckline
- Open back, lower ruched seam
- Front tropical floral hardware piece
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000401
Category Name: Casual Dresses
Price: $48.90
Availability: Out of Stock
Product Badge:- Ships Free
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Keep Them Curious Tie Back Mini Dress
This dress keeps it minimal from the front and magnetic from the back—the open cut and tie detail gives just enough drama while the rib knit smooths everything into place. It’s an easy yes for plans when simple feels the sexiest.
Fit & Features
- Rib knit fabric with subtle texture
- Boat neckline with long fitted sleeves and flared cuffs
- Bodycon silhouette through the bodice and skirt
- Open back design with wide band and tie-back closure
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000402
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy And Captivating Bodycon Mini Dress
All eyes on you. This off-the-shoulder ribbed mini dress hugs every curve in soft, stretchy knit with a foldover neckline that adds just the right amount of flirt. The long sleeves balance the bodycon fit for a look that’s equal parts cozy and captivating.
Fit & Features
- Soft rib knit stretch fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000405
Category Name: Casual Dresses
Price: $18.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Details Ponte Mini Dress
Structured, sleek, and a little daring. This ponte mini dress showcases chic details with its asymmetric mock neckline, knotted closures, and side slit detailing.
Fit & Features
- Smooth ponte knit fabric, minimal stretch
- Asymmetric mock neckline, short cap sleeves
- Knotted closures along the front
- Back zipper closure
- Form-hugging fit
- Side slit detail, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000406
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XL
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Bare It Boldly Open Back Mini Dress
Who knew soft could look this hot? This mini dress brings the drama with a low back cutout, halter neckline, and curve-hugging silhouette. Whether you're headed to dinner or turning heads at a party, this fit's got the bold factor locked.
Fit & Features
- Soft knit fabric with stretchy lining
- Scoop halter neckline with attached long sleeves
- Underwire bust design
- Open back cutout with adjustable halter tie
- Asymmetrical shark bite hem
- Runs true to size
Style Number/Barcode: 05102-000403
Category Name: Casual Dresses
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Yours Off-Shoulder Mini Dress
A little flirty, a little free—this off-shoulder mini dress brings effortless charm with every move. The flowy sleeves and fitted hem keep it soft, flattering, and ready for any occasion.
Fit & Features
- Soft knit stretchy fabric
- Off-shoulder neckline
- Long sleeves
- Fitted mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000524
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: PINK, BLACK
Available Size: S
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Frosted Charm Faux Fur Hem Mini Dress
This mini dress is the definition of winter glam—sleek brushed knit meets a plush faux fur hem that adds instant drama. It’s soft, stretchy, and serves that effortless luxe vibe from brunch to chic winter nights.
Fit & Features
- Brushed knit fabric with stretch
- Crew neckline
- Fitted long sleeves
- Bodycon silhouette
- Plush faux fur mini hem for a statement finish
- Runs true to size
Style Number/Barcode: 05102-000407
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bold Plans Tropical Floral Mini Tube Dress
A floral moment that knows it’s being noticed. This tropical floral mini tube dress hugs you in all the right places with a smooth, stretchy feel that’s made for warm nights, bold plans, and outfits that don’t blend in.
Fit & Features
- Smooth knit fabric, sewn-in lining
- High stretch for a body-hugging fit
- Large-scale tropical floral print
- Strapless straight-across neckline
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000413
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Postcard Pretty Halter Cutout Maxi Dress
Booked the dinner, ordered the spritz, now you need the dress. This halter maxi dress brings the drama with a rose detail, front cutout, and tiered skirt that moves like you planned this all along.
Fit & Features
- Lightweight woven fabric with abstract print
- Halter neckline with rosette detail
- Front cutout with twist front bodice
- Smocked back for stretch
- Tiered ruffled maxi skirt
- Runs true to size
Style Number/Barcode: 05102-000411
Category Name: Casual Dresses
Price: $62.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, L
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Vacation Mode Abstract Open Back Maxi Dress
This dreamy mesh maxi dress was made for golden hour plans, tropical cocktails, and dancing 'til dinner. Designed in an abstract print that brings the ocean and desert sky together, this halter dress features a draped cowl neckline, hardware straps, and open tie-back.
Fit & Features
- Abstract print, mesh-lined fabric
- Plunge cowl halter neckline with hardware
- Open tie-back design
- High side slit
- Form-hugging maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000409
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Sweet Intentions Flower Strapless Mini Dress
Soft details, confident energy. This strapless mini dress pairs a sweetheart neckline with a subtle cutout and floral accent for a look that feels romantic but never too precious.
Fit & Features
- Smooth knit fabric with knit lining, high stretch
- Strapless sweetheart neckline, no-slip strip
- Front cutout with floral trim detail
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000412
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Low Light Luxe Sequin Halter Mini Dress
Lights low, confidence high. This sequin halter mini is all about fluid shine and a plunging cowl neckline that moves with you—made for parties and nights out.
Fit & Features
- Sequin-embellished fabric
- Cowl halter neckline with hoop inserts
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000410
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S
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Desert After Dark Denim Mini Dress
Serving curves with a little edge. This denim halter mini dress features a plunging grommet V neckline and corset-inspired seams that sculpt your shape and keep all eyes exactly where you want them.
Fit & Features
- Denim fabric with color fade effect
- Halter neckline with grommet embellishments
- Corset seam construction
- Open back with zipper closure
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000415
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Weekend Wandering Open Back Maxi Dress
Light, airy, and made for unhurried afternoons that turn into early evenings. This gauze maxi drapes effortlessly, skims the body just right, perfect for shower celebrations, vacation, or a brunch.
Fit & Features
- Soft gauze fabric with lightweight drape, knit lining
- V-neckline with cutout detail
- Spaghetti straps
- Open back with tie, zipper and hook-eye closure
- Fitted waist flowing into a relaxed maxi skirt
- Runs true to size
Style Number/Barcode: 05102-000416
Category Name: Casual Dresses
Price: $56.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Undeniable Allure Halter Cutout Mini Dress
She doesn’t enter quietly—she arrives undeniable. A plunging halter cutout mini dress with bold metal hardware and a body-hugging fit that was made for rooftop nights, vacation dinners, and any plan that deserves extra.
Fit & Features
- Textured knit fabric, high stretch
- Sleeveless plunging V-neckline
- Dual circular metal hardware accents, waist cutouts
- Tie-back halter straps
- Open back, lower tie-back spaghetti straps
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000417
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L