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 Intentions Halter Mini Dress
Turn heads in this curve-loving ruched mini dress that’s all about sleek confidence. The halter neckline and off-shoulder sleeves give it that effortlessly sultry energy, while the front cutout keeps things daring yet refined. Perfect for date night plans or any moment you want to make unforgettable.
Fit & Features
- Sleek knit stretchy fabric
- Off-the-shoulder halter neckline, tie closure
- Fitted long sleeves
- Cutout bust
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000343
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Abstract Affair Mesh Mock Neck Dress
Art meets attitude. This abstract mesh dress brings the heat with its sheer long sleeves, curve-hugging silhouette, and daring open back. It’s bold, lightweight, and made for the nights you want all eyes on you.
Fit & Features
- Abstract floral print, mesh-lined stretch fabric
- Mock neckline, button closures
- Sheer fitted long sleeves
- Open back design
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000349
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lace Up and Take Over Mini Dress
This lace corset mini is equal parts sweet and daring — with a deep V neckline, faux leather lace-up bodice, and tiered lace skirt that moves like you already own the room. It’s that perfect mix of romantic texture and confident structure.
Fit & Features
- Lace-lined bodice with plunging V-neckline
- Sleeveless design, adjustable shoulder straps
- Faux leather corset waist with grommet lace-up front
- Back zipper and hook-eye closure
- Drop-waist seam
- Tiered lace-lined mini skirt
- Runs true to size
Style Number/Barcode: 05102-000352
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Plans Animal Print Mesh Halter Mini Dress
Wild plans call for a dress that knows exactly what it’s doing. This animal print mesh halter mini dress hugs through the waist with ruched shaping and flares out with playful tiers that move with you from dinner reservations to wherever the night decides to go.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Animal print
- Sleeveless halter neckline with tie-back straps, partially open back
- Metal hardware accent, keyhole bust cutout
- Ruched drop waist
- Tiered ruffled design, mini-length A-line fit
- Runs true to size
Style Number/Barcode: 05102-000350
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: In Stock
Available Color: RUST
Available Size: XS, S, M, L
Product Badge:- Sale
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Late Arrival Abstract Maxi Dress
Moody, sculpted, and impossible to ignore. This maxi dress hugs in all the right places with a plunging neckline and statement ring detail that feels made for vacations, sunset dinners, and GNOs!
Fit & Features
- Abstract print, mesh-lined fabric
- Strapless neckline with cutout and hardware inserts
- Form-hugging silhouette
- Maxi-length hemline
- Runs true to size
Style Number/Barcode: 05102-000348
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Twist of Fate Mini Dress
Sleek, sculpted, and a little unexpected. This halter mini dress stuns with its high neckline, open back, and drop waist silhouette that flatters every curve while keeping things effortlessly chic from mimosa brunches to date nights.
Fit & Features
- Slinky knit fabric, stretchy knit lining
- High halter neckline with tie closure
- Open back
- Drop waist seam
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000577
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Wild At Heart Lace Leopard A-Line Mini Dress
Turn up the heat in this sultry leopard mini dress. The fierce leopard print, lace bust, and flared skirt make it the perfect mix of wild and romantic. Whether it’s a night out or a wine bar evening, this dress brings all the allure.
Fit & Features
- Leopard print, mesh fabric, stretchy knit lining
- Lace bust sweetheart neckline, underwire cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000353
Category Name: Casual Dresses
Price: $18.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fall for Knit Long Sleeve Mini Dress
Cozy, flattering, and totally fall-coded. This ribbed knit mini dress features a sweetheart neckline and subtle ruching that shapes your silhouette while keeping it soft and effortless. Pair it with knee-high boots for a perfect fall day out.
Fit & Features
- Hacci rib knit stretch fabric
- Sweetheart neckline, ruched bust seam
- Fitted long sleeves
- A-line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000354
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty And Flowy Ribbed Knit Strapless Skater Dress
Ready before the group chat even replies. This ribbed knit strapless skater dress hugs through the bodice with a flirty drop waist and flowy skirt that moves with you from brunch plans to last-minute invites.
Fit & Features
- Ribbed knit fabric, high stretch
Strapless straight-across neckline - Drop waist design
- Godet detailing
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 06005-000008
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Ribbed knit fabric, high stretch
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Cutest Plans Floral Eyelet Corset Skater Dress
Your group chat is already asking where you got it. This floral eyelet corset skater dress cinches you in with a sculpted bodice and flares out into the cutest twirl-ready silhouette for brunch dates, garden parties, and every camera roll moment in between.
Fit & Features
- Floral eyelet woven fabric, tulle and knit linings
- Sleeveless sweetheart neckline, ruched bust, small cutout, tie-front detail
- Underwire bust support
- Tie-shoulder straps, side zipper and hook-eye closure
- Corset bodice with boning, V-shaped waist, ruffled trim
- Lace-up back design, short skater silhouette
- Runs true to size
Style Number/Barcode: 05101-000130
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunkissed Curve Knit Midi Dress
This striped midi dress was made to highlight every curve with a sculpting rib texture, front cutout detail, and side slit. Dress it up with heels for a night out or keep it elevated with sandals for a chic daytime moment.
Fit & Features
- Striped print, rib knit fabric
- Sweetheart neckline, cutout bust accent
- Adjustable spaghetti straps
- Bodycon fit
- Dual side slits
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000084
Category Name: Casual Dresses
Price: $19.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lace-Up Moment Sheer Long Sleeve Mini Dress
Bring the drama without even trying—this long sleeve mini dress is sheer perfection. With a lace-up front and ruffle trim, it’s the flirty and fab style your night-out look needs.
Fit & Features
- Sheer mesh fabric with partial knit lining, high stretch
- Plunging V-neckline, lace-up front with tie closure, ruffle trim
- Sheer long fitted sleeves
- Hidden back zipper with hook-eye closure
- Drop waist seam
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05103-000401
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sheer mesh fabric with partial knit lining, high stretch
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Petal Noir Floral Chiffon Maxi Dress
This halter maxi dress stuns with a draped cowl neckline, bold floral print, and a daring open back that leaves a lasting impression. Flowing and form-flattering, it’s your go-to for romantic date nights and elevated occasions.
Fit & Features
- Floral print, chiffon-lined fabric
- Halter cowl neckline
- Open back design, zipper and hook-eye closure
- Curve-hugging silhouette
- Flowy maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000577
Category Name: Casual Dresses
Price: $9.97 $56.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
Product Badge:- Sale
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Buttoned Up Charm Off-The-Shoulder Mini Dress
Sophisticated with a sultry twist, this rib knit mini serves clean lines and gold button details that pop. Perfect for lunch dates, weekend looks, or when you want polished but playful.
Fit & Features
- Rib knit fabric, moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Button front accents
- Faux front pockets
- Bodycon fit, mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000155
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Allure Cable Knit Mini Dress
Chic meets snuggly. This off-the-shoulder sweater dress hugs your curves with cable-knit texture while keeping things flirty and polished—perfect for autumn plans, latte runs, or cozy dinners out.
Fit & Features
- Cable knit fabric, moderate stretch
- Folded off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000157
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Quiet Luxe Off-The-Shoulder Maxi Dress
Minimal effort, maximum impact. This off-the-shoulder maxi brings that sleek, sculpted vibe with a foldover neckline and curve-hugging silhouette that’s equal parts timeless and sultry.
Fit & Features
- Soft rib knit stretchy fabric
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Center back slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 06005-000183
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild Bloom Mesh Halter Romper
Flirty meets fierce. This ruffle mesh halter romper blends floral and leopard prints for the ultimate wild-but-feminine vibe—perfect for concerts, birthdays, or any plan that calls for a little extra drama.
Fit & Features
- Floral leopard print, mesh-lined stretchy fabric
- Cowl halter neckline, tie closure
- Open back, spaghetti strap tie
- Ruffled trims
- Short-length hem, stretchy knit shorts lining
- Runs true to size
Style Number/Barcode: 06503-000153
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: LEOPARD
Available Size: XS, S, M, L
Product Badge:- Back In Stock
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Weekend Plans Ruffle A-Line Romper
Your plans just found their outfit—this romper is all about fun with a flirty edge. The tie-back halter straps, ruffle overlay, and A-line fit make it a go-to for nights out or weekend parties.
Fit & Features
- Smooth knit fabric, high stretch
- Sleeveless V-neckline
- Tie-back halter straps, partially open back
- Ruching, drop waist
- Mini-length tiered ruffle overlay, hidden fitted shorts
- Romper in size small is 29" shoulder to hem with a 9" front rise and a 1" inseam
- Runs true to size
Style Number/Barcode: 06503-000155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Plans Plaid Romper
Sweet, flirty, and made for your next “what should I wear?” moment. This strapless plaid romper brings easy charm with its ruched bodice, ruffle skirt detail, and bow accent that seals the deal.
Fit & Features
- Plaid print, stretchy knit fabric
- Strapless neckline with front bow detail
- Ruched, fitted bodice
- Tiered ruffle mini-length hem, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000164
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Darling Off-Shoulder Skater Dress
This chiffon mini dress features an off-the-shoulder ruffle neckline with delicate lace trim and a flirty skater skirt, creating a dreamy silhouette perfect for family brunches, bridal events, and dressy occasions.
Fit & Features
- Chiffon-lined fabric
- Ruffle trim off-the-shoulder neckline, tie-front
- Corset-seamed bodice
- Skater silhouette, drop waist seam
- Lace trim mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000684
Category Name: Casual Dresses
Price: $54.90
Availability: Out of Stock
Product Badge:- Ships Free
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Soft Stunner Off-The-Shoulder Mini Dress
A little cozy, a little glam—this off-the-shoulder knit mini brings that effortless “I just threw this on” sparkle. The foldover neckline and body-hugging fit keep things soft, sleek, and low-key irresistible.
Fit & Features
- Rib knit stretchy fabric with shimmer
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000197
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Attitude Ribbed Knit Off-The-Shoulder Midi Dress
A sleek off-the-shoulder midi dress with just the right dose of attitude. The ribbed knit snatches softly, the cutout adds that chic twist, and the midi length keeps the whole look effortlessly elevated.
Fit & Features
- Ribbed knit fabric, high stretch
- Off-the-shoulder sweetheart neckline, no-slip strip, center hardware accent
- Keyhole cutout below the bust
- Long fitted sleeves
- High-cut front slit
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-000222
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet Twist Bodycon Mini Dress
Meet the mini that serves soft vibes in the front and a major moment in the back. This long sleeve dress hugs your shape with a sleek, stretchy feel while the scoop neckline keeps things subtly flirty. But the real plot twist? A double-twist open-back design that turns every exit into an entrance.
Fit & Features
- Textured knit stretch fabric
- Scoop neckline
- Fitted long sleeves
- Statement cutout back, double-twist design
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000220
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Unforgettable Entrance Plunge Neck Maxi Dress
This maxi dress doesn’t blend in—it arrives. This plunging cowl neck maxi dress drapes smoothly through the body with a halter neckline that feels bold, polished, and intentionally striking. Pair with heels for date night, dressy celebrations, or a sultry vacation look.
Fit & Features
- Smooth knit-lined fabric with high stretch
- Halter neckline with plunging cowl front
- Open back with adjustable tie closure
- Fitted bodice that skims the waist and hips
- High side slit for movement
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05101-000736
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free