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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Plans On Lock Denim Drop Waist Skater Dress
Outfit secured in under 5 seconds. This drop waist mini dress hugs through the bodice then flares into layered ruffles for that easy, playful finish made for plans that pop up last minute.
Fit & Features
- Structured stretch denim fabrication
- Sleeveless square neckline
- Wide shoulder straps
- Fitted bodice with drop waist silhouette
- Tiered ruffle skirt
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000506
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M
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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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Flirty Babe Polka Dot Mesh Ruffle Mini Dress
Flowy, flirty, and impossible to ignore. This polka dot mesh ruffle mini dress hugs in all the right places with soft ruching and a playful hem that moves with you.
Fit & Features:
- Mesh fabric with knit lining, high stretch
- All-over polka dot print
- Sleeveless plunging V-neckline
- Tie-back halter straps, partially open back
- Ruched body, drop waist design
- Tiered ruffled mini-length hem, fitted A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000515
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: BLACK
Available Size: XS
- Mesh fabric with knit lining, high stretch
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All Eyes on You Lace Trim Mini Dress
This one understands the assignment. A sweetheart neckline with lace trim and a flirty drop-waist skirt that moves just right—polished up top, playful from every angle.
Fit & Features
- Woven rayon fabric with smooth structured feel, sewn-in knit panty lining
- Strapless sweetheart neckline with lace trim detail, non-slip grip lining
- Back zipper and hook-eye closure
- Fitted bodice with center lace inset
- Drop waist seam for a flattering silhouette
- Tiered skater skirt with mini length
- Runs true to size
Style Number/Barcode: 05102-000517
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, M, L
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Sweet Citrus A-Line Mini Dress
Like sunshine in outfit form. This lemon print stretch linen mini dress features a square neckline with a delicate bust tie and a flirty A-line skirt that’s made for brunch dates, vacations, and sunny day plans.
Fit & Features
- Citrus print, cotton-blend woven fabric, woven lining
- Square neckline with tie front
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-line fitted silhouette, pipe trim
- Flared mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000518
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Forever Yours Floral Romper
Steal the scene in this romantic flocked floral romper featuring a sultry halter neckline and flirty ruffled hem. The open strappy back adds just the right amount of drama for your weekend plans.
Fit & Features
- Flocked velvet floral pattern, mesh-lined fabric
- Plunge cowl halter neckline, tie closure
- Open dual tie-back design
- Form-hugging bodice
- Ruffled mini-length hem, shorts lining
- Runs true to size
Style Number/Barcode: 06503-000193
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BURGUNDY
Available Size: S
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RSVP Me Drop Waist Skater Dress
Plans confirmed. Outfit secured. This textured knit skater dress sculpts through the sweetheart bodice and falls into a drop waist that brings just the right amount of flirt to dinner dates, birthdays, and spontaneous night-out plans.
Fit & Features
- Textured knit fabric with stretch
- Sleeveless sweetheart neckline, padded bust, mini bow detail
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Sewn-in panty lining with snap-button closures
- V-shaped drop waist
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000519
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Major Charm Polka Dot Halter Maxi Dress
A little retro, a lot irresistible. This polka dot halter maxi dress hugs your shape with a plunging neckline and open back that brings effortless drama to dates, celebrations, and weekend brunch.
Fit & Features
- Polka dot print, mesh-lined fabric
- Fitted silhouette with plunging halter neckline
- Sewn-in padded bra cups
- Open back, zipper and hook-eye closure
- Floor length hem
- Runs true to size
Style Number/Barcode: 05102-000521
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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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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Soft Focus Confidence Bodycon Mini Dress
Clean lines, smooth moves. This brushed knit mini dress hugs just right with a sleek high neckline and long sleeves, making it an easy yes for brunch, coffee dates, and everything that turns into plans.
Fit & Features
- Brushed knit fabric with a smooth, stretchy feel
- Sleek high neckline
- Long fitted sleeves
- Bodycon mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000528
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet And Social Polka Dot Mesh Halter Mini Dress
Flirty plans called, and this answered. This polka dot mesh halter mini dress hugs in all the right places with a ruched fit and ruffled hem that’s ready for parties, date nights, and every photo in between.
Fit & Features
- Sheer mesh fabric with lining
- Polka dot print
- Sleeveless V-neckline
- Halter tie-back straps, partially open back
- Mini-length ruffled hem
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000535
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Weekend Crush Striped Halter Midi Dress
This is your “I didn’t overthink it, I just look this good” dress. The halter neckline and bodycon fit do all the work, while the soft stripes keep it flirty but low-key. Brunch, date night, or last-minute plans—she’s already ready.
Fit & Features
- Halter neckline
- Bodycon silhouette
- Midi length
- Soft stretch fabrication
- Allover stripe pattern
- Runs true to size
Style Number/Barcode: 05102-000523
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: MULTI
Available Size: XS, S, M, L
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Soft Intentions Off-Shoulder Midi Dress
Soft, sculpted, and quietly confident. This faux cashmere midi dress drapes off the shoulders with a foldover neckline and body-hugging fit that accentuates your curves.
Fit & Features
- Faux cashmere knit with a smooth, knit lining
- Foldover off-the-shoulder neckline
- Fitted long sleeves
- Bodycon midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000526
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Starstruck Denim Corset Skater Dress
Serving country concert plans with a little extra attitude. This star embroidered denim skater dress hugs in all the right places with a corset-inspired lace up front and flirty tiered skirt that’s ready for boots, bangles, and fab camera roll pics.
Fit & Features
- Denim fabric, star embroidered patches
- Strapless, subtle sweetheart neckline
- Lace-up front design
- Back zipper closure
- Drop waist seam, tiered ruffled design
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000534
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: MEDIUM, DENIM
Available Size: XS, S, M, L
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Cute Entrance Polka Dot Ruffle Skater Dress
Polka dots, ruffles, and a strapless moment? Say less. This flirty skater dress features a stretchy smocked bodice and tiered ruffled silhouette that’s made for brunch dates, party pics, and any plan that calls for a cute entrance.
Fit & Features
- Woven fabric
- Polka dot print
- Strapless straight-across neckline, ruffled trim
- Stretchy smocked bodice
- Tiered ruffled design
- Short skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000532
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: BLACK
Available Size: XS
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RSVP Ready Sash Mini Dress
When the invite says dress up, this dress understood the assignment. This eyelet tube bodycon mini dress hugs in all the right places and finishes with a draped side sash that brings the drama to showers, parties, or day dates.
Fit & Features
- Eyelet fabric, knit lining
- Tube strapless necklinenon-slip grip lining
- Attached side ruffle sash
- Bodycon mini-length fit
- Runs true to size
Style Number/Barcode: 05102-000530
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: PINK, WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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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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Ocean Daydream Seashell Mini Dress
Catch flights or just compliments in this mini dres that hugs just right with delicate shell details and a breezy open back made for sunny getaways and golden hour dinners.
Fit & Features
- Crochet knit-lined fabric with seashell embellishments
- V-neckline
- Spaghetti straps shape the lace-up back design
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000536
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: NATURAL
Available Size: S, L
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Chic Moments Bodycon Mini Dress
Clean lines. Bold presence. This chic bodycon mini dress hugs just right with a sleek mock neckline that keeps the vibe elevated, whether you’re heading out late or dressing up a last-minute plan.
Fit & Features
- Sleeveless mock neckline
- Mini-length hem
- Bodycon silhouette
- Smooth knit fabric with high stretch
- Runs true to size
- Please note the necklace is not included
Style Number/Barcode: 05102-000539
Category Name: Casual Dresses
Price: $30.90
Availability: In Stock
Available Color: BLACK, BURGUNDY, BROWN, NAVY
Available Size: XS, S, M, L, XL
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Last Minute Plans Denim Skater Dress
This dress was made for day or night casual plans when you wanna look cute. The structured corset-inspired bodice flatters in all the right places while the flirty skater skirt keeps it playful.
Fit & Features
- Dark wash denim fabric with stretch
- Sweetheart neckline
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- Corset-seamed bodice
- Skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000538
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M, L
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Dinner Plans Locked Mock Neck Wrap Midi Dress
Clean lines, subtle drama, zero hesitation. This ribbed midi dress hugs in all the right places with a sleek wrap detail that does the talking from reservations to late plans.
Fit & Features
- Ribbed knit fabric with stretch
- Mock neckline with long sleeves
- Wrap-style skirt with hardware detail
- Front slit at hem
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000544
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Esmerelda Denim Rhinestone Bodycon Mini Dress
Special Occasion
Built for that slow-motion entrance, this denim bodycon mini dress catches the light with every step thanks to its rhinestone-studded corset design. Luxe structure meets after-dark sparkle, giving you a look that feels polished, powerful, and impossible to forget.
Fit & Features
- Denim fabric with allover rhinestone embellishment
- Strapless neckline with structured corset bodice, flexible boning
- Back zipper and hook-eye closure
- Front pockets for convenience
- Bodycon mini silhouette
- Runs true to size
Where to Wear:
GNO, bachelorettes, date nights, birthdays, holiday parties
Style Number/Barcode: 05001-000634
Category Name: Casual Dresses
Price: $64.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S
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Hot Plans Tropical Tube Mini Dress
Booked, busy, and dressed for it. This tropical floral mini dress hugs in all the right places with a sleek strapless fit—made for vacations, beach weekends, and last-minute plans that turn into everything.
Fit & Features
- Tropical floral print, stretchy knit fabric
- Tube strapless neckline
- Bodycon mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000547
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Soft Spoken Confidence Rib Knit Mini Dress
Low effort, high payoff. This rib knit foldover off-the-shoulder mini dress hugs just enough while keeping things comfortable, perfect for dinners that turn into late plans.
Fit & Features
- Soft rib knit fabric with stretch and lining
- Foldover off-the-shoulder neckline
- Long sleeve design
- A-line mini silhouette
- Runs true to size
Style Number/Barcode: 05102-000545
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: In Stock
Available Color: BURGUNDY, BROWN
Available Size: XS, S, L, M
Product Badge:- Sale