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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Pretty Plans Eyelet Mini Dress
Caught feelings for this one instantly. This eyelet dress feels light and playful, perfect for brunch dates, daytime plans, or wherever the mood takes you.
Fit & Features
- Eyelet knit fabric, smooth knit lining
- V-neckline
- Adjustable spaghetti straps
- Fitted bodice
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000471
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
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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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Backstage Flirt Denim Skater Dress
Caught feelings for a denim moment this good. This plunge halter mini dress brings the drama with an open tie back and skate silhouette that’s made for weekend plans and concerts.
Fit & Features
- Denim fabric, slight stretch, built-in panty lining
- Plunge halter neckline, tie straps
- Button front closures
- Open back with tie
- Drop waist seam
- Skater silhouette, mini-length raw hem
- Runs true to size
Style Number/Barcode: 05102-000474
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: PINK
Available Size: XS, S, M, L
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Sunny Day Invites Eyelet Knit Skater Dress
This adorable eyelet knit skater dress will have you instantly weekend-ready. The short dress hugs up top, flares just right, and is basically made for last-minute brunches and sunny day invites.
Fit & Features
- Eyelet knit fabric with knit lining, high stretch
- Sleeveless V-neckline
- Halter tie-back straps, partially open back
- Drop waist design, V-shaped seam
- Mini-length skater silhouette
- Runs true to size
Style Number/Barcode: 05102-000694
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L, XL
Product Badge:- Best Seller
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Serving Sweetness Denim Mini Dress
This lace-up denim skater dress features a plunge V-neckline, structured bodice, and a playful drop waist skirt that’s made for concerts, festivals, and every plan in between.
Fit & Features
- Denim fabric, built-in pant knit lining, some stretch
- Plunge halter V-neckline
- Structured bodice with lace-up design
- Drop waist seam
- Back zipper with hook-eye closure
- Pleated skater mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000478
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Flirty Fab Polka Dot Halter Mini Dress
This polka dot halter mini dress is ready for your weekend plans. It features a draped cowl neckline and curve-hugging bodycon fit that keeps you looking flirty, fab, and right on time for every outing.
Fit & Features
- Sleek knit fabric with high stretch
- Polka dot print
- Sleeveless V-neckline, draped cowl design
- Tie-back halter straps, partially open back
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000475
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: BROWN
Available Size: XS, S, M, L
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Effortless Impact Mock Neck Midi Dress
This midi is your secret weapon—clean, sculpting, and quietly commanding. The ribbed knit dress smooths and contours while the mock neck adds that cool, editorial structure that never tries too hard.
Fit & Features
- Rib knit fabric
- Mock neckline
- Smooth bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000479
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: HUNTER
Available Size: XS, S, M
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Second Look Open Back Midi Dress
Simple from the front, unforgettable from the back. This ribbed halter midi dress features a plunging neckline and open back with subtle ruching that hugs your shape and keeps the look smooth, polished, and confidently put together.
Fit & Features
- Soft rib knit stretch fabric
- Plunge halter neckline
- Open back design with subtle ruching
- Bodycon midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000482
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: NAVY
Available Size: XS, S, M, L
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Daydream Bloom Floral Print Midi Dress
This is the kind of dress that makes every plan feel a little prettier. The fitted bodice and flowy skirt create that effortless shape, while the soft floral print keeps things light and romantic.
Fit & Features
- Woven fabric, soft floral print, woven lining
- Square neckline, tie bust keyhole accent
- Adjustable spagehtti straps
- Stretchy smocked back panel, side zipper and hook-eye closure
- Fitted bodice with button accents
- Drop waist seam, a-line midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000481
Category Name: Casual Dresses
Price: $62.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S
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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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Effortless Flirt Babydoll Mini Dress
Floaty, flirty, and effortless in the best way. This babydoll mini dress brings that easy, throw-on-and-go feel with a breezy fit that moves with you from daytime plans to last-minute outings.
Fit & Features
- Cotton-blend fabric with lining
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Partially smocked back
- Mini-length asymmetric hem, subtle distressed detailing
- Flowy babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000485
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Denim Days Button Front Mini Dress
Denim, but make it plans. This button-up mini dress cinches you in with a flattering fit and an unexpected back buckle moment that turns heads anywhere you go.
Fit & Features
- Dark wash denim
- Strapless tube neckline
- Button-up front
- Adjustable back buckle
- Curve-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000490
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: DARK, DENIM
Available Size: XS, S, M
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Flirty Flowy Chiffon Strapless Babydoll Dress
Made for spontaneous plans and extra mirror checks. This strapless chiffon babydoll dress brings the flirty vibes with flowy layers, a mini hem, and that effortlessly dressed-up look.
Fit & Features
- Sheer chiffon fabric with lining
- Strapless sweetheart neckline
- Hidden side zipper and hook-eye closure
- Flowy, tiered, ruffle design
- Mini-length hem
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-000489
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- New Arrival
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Ready In Five Tie-Back Mini Dress
This A-line mini dress is your “I have nothing to wear” fix—handled. A flirty ruffled dress with a tie-back detail that cinches just right and a flowy skirt made for last-minute plans and weekend brunches.
Fit & Features
- Woven fabric
- V-neckline
- Spaghetti straps
- Tie-back detail
- A-line fit
- Layered ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000486
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: WHITE, YELLOW, SAGE
Available Size: L, XL, S, M, XXS, XS
Product Badge:- Best Seller
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Cutie Vibe Lace Strapless A-Line Mini Dress
Cute plans only—this one’s already booked. This lace strapless A-line mini dress hugs up top and flares out with an easy, flirty fit that’s made for last-minute invites.
Fit & Features
- Sheer lace fabric with knit lining, high stretch
- Strapless straight-across neckline
- Mini-length asymmetric hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000492
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: LIGHT, BLUE
Available Size: XS, S, M, L
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Dreamy Eyelet Ruffle Mini Dress
This sweet eyelet dress brings soft romance with a playful twist. The square neckline, puff sleeves, and tiered ruffle skirt create a flattering A-line silhouette that feels effortlessly feminine. Perfect for brunch dates, garden parties, or sunny day plans.
Fit & Features
- Eyelet fabric, knit lining
- Square neckline
- Short puff sleeves
- Fitted bodice
- Drop waist A-line silhouette
- Tiered ruffle mini hem
- Runs true to size
Style Number/Barcode: 05102-000493
Category Name: Casual Dresses
Price: $34.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Sunny Days Crochet A-Line Mini Dress
Booked, packed, and already planning the outfit. This A-line mini dress with a crochet bust overlay and lace-up back brings that effortless Euro summer vibe with a flirty, easy fit.
Fit & Features
- Linen-like fabric, smooth woven lining
- V-neckline, crochet bust overlay, tie bust front
- Spaghetti straps
- Strappy tie-back design
- Princess seam, A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000494
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Sweet With A Twist Polka Dot Halter Mini Dress
Soft, flirty, and just a little daring. This halter mini dress pairs classic polka dots with a lace-trim neckline and open back that feels romantic without trying too hard—easy to dress up, impossible to forget.
Fit & Features
- Polka dot print, knit fabric with lining
- Halter neckline with lace trim detail
- Open back with adjustable tie closure
- Mini-length silhouette, subtle flared hem
- Runs true to size
Style Number/Barcode: 05102-000497
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daytime Vibe Floral Eyelet Strapless Midi Dress
Currently planning your next cute daytime moment. This floral eyelet strapless midi dress hugs up top with a smocked fit, then flows out for that easy, throw-on-and-go vibe—perfect for brunch, beach days, or last-minute plans.
Fit & Features
- Woven floral eyelet fabric
- Strapless straight-across neckline
- Fitted smocked bodice
- Midi-length flowy A-line silhouette
- Ruffled hem
- Runs true to size
Style Number/Barcode: 05102-000498
Category Name: Casual Dresses
Price: $69.90
Availability: In Stock
Available Color: WHITE
Available Size: XS
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All The Compliments Floral Mini Dress
Soft, flirty, and already getting compliments. This floral eyelet mini hugs in all the right places with a sweetheart neckline and ruffle hem that feels made for any occasion.
Fit & Features
- Ditsy floral print, eyelet knit fabric
- Sweetheart neckline, tie bust keyhole
- Short puff sleeves
- Bodycon fit, ruffle trim mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000501
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Bare It Beautiful Floral Tube Midi Dress
No straps, no stress, just compliments. This floral printed midi dress sculpts in a smooth, strapless tube silhouette with a sleek bar back detail that keeps it secure while you own every spring RSVP.
Fit & Features
- Floral printed stretch-lined fabric
- Strapless tube silhouette
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05101-001188
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: YELLOW
Available Size: M
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Sunny Day Cutie Gingham Midi Dress
Brunch plans, farmer’s market, and cute coffee dates—this midi dress is ready for all of it. This gingham tube midi dress features a flattering strapless neckline and an A-line fit that keeps your look effortlessly sweet.
Fit & Features
- Gingham print, woven fabric, knit lining
- Strapless tube neckline
- Stretchy smocked back
- Side zipper and hook-eye closure
- Drop waist seam
- A-line fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000503
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: SAGE
Available Size: XS, S, M, L
Product Badge:- Best Seller
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Quietly Captivating Floral Midi Dress
Soft florals, sleek lines, and just enough drama. This floral midi dress skims the body with delicate straps and a front slit that moves with you, making it an easy pick for date nights, weddings, or shower celebrations.
Fit & Features
- Floral pattern on smooth, knit stretchy fabric
- Square neckline with spaghetti straps
- Front slit accent
- Form-hugging midi silhouette
- Runs true to size
Style Number/Barcode: 05102-000505
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: PLUM
Available Size: XS, S, M, L, XL
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Modern Fairytale Lace Ruffle Mini Dress
Perfect for bridal events, birthday dinners, or any moment that deserves a little extra glow, this mini dress brings soft romance. Just add delicate heels and jewelry for a look that feels effortless but completely put together.
Fit & Features
- Lace-lined fabric
- Strapless neckline
- Bodycon fit
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000508
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: WHITE, SAGE
Available Size: L, XS, S, M
Product Badge:- Best Seller