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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Lowkey Bold Studded Denim Bodycon Dress
Confident from every angle, this denim mini doesn’t wait for an invite. The halter neckline, body-hugging fit, and subtle stud details make it an easy yes for nights out, concerts, or festivals.
Fit & Features
- Denim fabric with vintage-inspired wash
- Halter sweetheart neckline with studded trim
- Front zipper closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000440
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: BLACK, DENIM
Available Size: XS, S, M, L
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Make Plans Eyelet Ruffle Mini Dress
This mini dress is already the answer. A plunging eyelet halter mini with a snatched waist and tiered ruffle skirt, perfect for weekend plans or casual celebrations.
Fit & Features
- Eyelet knit fabric, knit lining
- Halter neckline, tie straps
- Fitted bodice
- Tiered layered ruffle mini-length hem
- Curve-hugging fit
- Runs true to size
Style Number/Barcode: 05102-000448
Category Name: Casual Dresses
Price: $32.90
Availability: In Stock
Available Color: WHITE
Available Size: XXS, XS, S, M, L
Product Badge:- Best Seller
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Own The Room Faux Suede Mini Tube Dress
Minimal effort, maximum impact—that’s the vibe. This faux suede mini tube dress hugs in all the right places with a sleek, sculpted feel that’s made for stepping out and owning the room.
Fit & Features
- Faux suede fabric, moderate stretch
- Strapless straight-across neckline
- Lace-up trims
- Mini-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000447
Category Name: Casual Dresses
Price: $52.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L
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Sunlit Escape Cutout Mini Dress
This strapless mini dress feels like a vacation—even if you’re just stepping out. The strapless neckline keeps it clean, while the beaded detailing and side cutout bring an unexpected flair.
Fit & Features
- Linen-like fabric
- Strapless tube neckline
- Side cutout with a beaded design
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000444
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Sunset Siren Cutout Bodycon Mini Dress
Serving sunkissed goddess with zero effort. This cutout bodycon mini dress hugs in all the right places, with sun-shaped hardware that turns a simple night out into a full-style statement.
Fit & Features
- Textured knit fabric, high stretch
- Strapless sweetheart neckline
- Dual cutouts at the bodice
- Metal sun-shaped hardware accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-001140
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: WHITE
Available Size: XS, S, M, L
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Star Struck Denim Tube Mini Dress
Not your basic denim moment. This strapless mini dress features bold star paneling with a curve-hugging fit that feels equal parts playful and put-together for festivals or last-minute plans.
Fit & Features
- Denim fabric with stretch
- Strapless tube neckline with belt loop accents
- Star pattern, back zipper closure
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000442
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Vacation Muse Floral Halter Maxi Dress
This is the dress that makes every plan feel like a getaway. The plunging halter keeps it bold, while the floral appliqué brings that playful, standout detail.
Fit & Features
- Statement floral applique, stretch knit fabric
- Plunge halter neckline
- Open back design with tie
- Center back slit
- Form-hugging maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-000446
Category Name: Casual Dresses
Price: $45.90
Availability: In Stock
Available Color: YELLOW
Available Size: XS, S, M, L
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Sweep Me Away Ribbed Off Shoulder Midi Dress
This is that “effortless but still unbelievably chic” dress you reach for when you want comfort without sacrificing the vibe. The ribbed knit hugs smoothly, the foldover neckline drapes just right, and the side slit keeps things subtly daring.
Fit & Features
- Soft ribbed knit fabrication, smooth lining
- Foldover off shoulder neckline
- Long fitted sleeves
- Side slit design
- Midi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000452
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: In Stock
Available Color: BLACK
Available Size: XS, S
Product Badge:- Sale
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Pretty Plans Pending Floral Tube Mini Dress
Romantic from every angle, no overthinking required. This floral tube mini dress hugs smoothly and easy, making it the kind of dress you grab when the plan is cute but the vibe is confident.
Fit & Features
- Floral pattern, knit fabric
- Strapless tube neckline
- Bodycon silhouette
- Sleek mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000456
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: PINK
Available Size: S, M, L
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Worth The RSVP Halter Ruffle Mini Dress
When the invite says dress up, this is the answer. The halter mini dress shapes through the waist with soft ruching and finishes with tiered ruffles that move every time you do.
Fit & Features
- Soft knit fabric with stretch and lining
- Plunge halter V-Neckline
- Ruched bodice
- A-line mini silhouette
- Tiered ruffle mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000455
Category Name: Casual Dresses
Price: $38.90
Availability: In Stock
Available Color: RED, CHARTREUSE-2, BLACK-2
Available Size: XS, S, M, L
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Golden Hour Glow Metallic Crochet Mini Dress
Golden hour glow mood. This metallic crochet one-shoulder mini dress hugs in all the right places and shows up ready for rooftop plans, dinners, and anything that turns into a photo moment.
Fit & Features
- Metallic crochet knit fabric, moderate stretch
- Sleeveless one-shoulder neckline, tank strap
- Metal flower hardware accents
- Back zipper closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000451
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: NATURAL
Available Size: XS, S, M, L
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Desert Daydream Fringe Maxi Dress
She moves, and the dress follows. This fringe maxi dress brings soft movement and a flattering cutout fit that feels made for festivals, country concerts, and golden hour plans!
Fit & Features
- Crochet fabric with short lining
- V-neckline, adjustable spaghetti straps
- Side cutout designs, side zipper and hook-eye closure
- Cascading long fringe
- Short bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000450
Category Name: Casual Dresses
Price: $49.90
Availability: In Stock
Available Color: IVORY
Available Size: XS
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Sunlit Plans Halter Tiered Skater Dress
Soft, flirty, and made for daylight plans that turn into something more. This halter skater dress balances a sculpted top with a playful tiered skirt for an easy look that feels styled the second you slip it on.
Fit & Features
- Smooth stretch fabrication
- Halter neckline with scoop front
- Drop waist with tiered skater skirt
- Mini length silhouette
- Runs true to size
Style Number/Barcode: 05102-000457
Category Name: Casual Dresses
Price: $43.90
Availability: In Stock
Available Color: YELLOW
Available Size: L
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Classy Icon Open Back Midi Dress
Minimal effort, maximum double takes. This sleeveless crew neck midi dress keeps it clean in the front and steals the scene with an open back and tie, perfect for everything on your spring calendar.
Fit & Features
- Rib knit fabric, soft lining
- Sleeveless crew neckline
- Open back with tie
- Form-hugging fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-000458
Category Name: Casual Dresses
Price: $36.90
Availability: In Stock
Available Color: WHITE
Available Size: M
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Naturally Cool Denim Lace-Up Skater Dress
Easy, relaxed, and low-key cool. This strapless denim skater dress keeps it casual up top with a structured fit that feels effortless from daytime plans to concerts.
Fit & Features
- Denim light wash fabric with slight stretch
- Strapless neckline, non-slip grip trim
- Structured bodice with front lattice lace-up detail
- Skater silhouette
- Flared mini-length hem, built-in knit stretchy shorts lining
- Back zipper and hook-eye closure
- Runs true to size
Style Number/Barcode: 05102-000459
Category Name: Casual Dresses
Price: $54.90
Availability: In Stock
Available Color: LIGHT, DENIM
Available Size: XS, S, M, L
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Golden Hour Groove Crochet Halter Maxi Dress
Vacation energy, locked in. This striped texture crochet knit maxi dress features a plunge halter neckline with wooden hoop inserts and an open back that feels equal parts effortless and elevated. Pair with strappy sandals for your upcoming getaway.
Fit & Features
- Crochet striped texture knit, smooth knit lining
- Plunge halter neckline with wood hoop inserts, tie closure
- Open back
- Side slit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000461
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: RED
Available Size: XS, S, M, L
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Effortlessly Polished Mock Neck Mini Dress
This is the kind of dress you reach for when you want to look pulled together without overthinking it. Clean lines, a smooth ribbed fit, and a mock neck give it that quiet confidence that works day to night with a quick switch of shoes.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Mock neckline
- Long fitted sleeves
- Bodycon silhouette, mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000460
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daytime Darling Eyelet Mini Dress
Caught the vibe and didn’t think twice. This puff sleeve eyelet mini dress hugs just right with a flirty tie front—perfect for brunch dates, daytime plans, and those “I look cute today” moments.
Fit & Features
- Eyelet knit fabric
- Sweetheart neckline, tie bust keyhole cutout accent
- Puff short sleeves
- Princess seam detailing
- A-line mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000462
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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Pretty Plans Chiffon And Lace Skater Dress
Booked, busy, and dressed like it. This chiffon and lace skater dress gives you that soft, floaty fit that moves with you from daytime plans to whatever the night turns into.
Fit & Features
- Lightweight chiffon fabrication, lace trim woven lining
- Sleeveless V-neckline with delicate lace insert
- Spaghetti straps
- Flared skater silhouette
- Adjustable waist tie
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000463
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: IVORY
Available Size: XS, S, M, L
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Flirt With The Breeze Skater Mini Dress
This flowy skater dress was made for sunny days. It features a flattering V-neckline and a breezy silhouette that moves with you from brunch to beachside strolls.
Fit & Features
- Cotton fabric, woven cotton lining, delicate embroidery
- V-neckline
- Adjustable spaghetti straps
- Tiered ruffled skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000465
Category Name: Casual Dresses
Price: $42.90
Availability: In Stock
Available Color: BLUE
Available Size: XS, S, M, L
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Getaway Mood Tropical Floral Halter Maxi Dress
Lightweight, curve-loving, and made to move with you. The airy sheer mesh fabric and tropical floral print bring a bold edge that feels right for nights out and getaway moods.
Fit & Features
- Sheer mesh fabric with knit lining, high stretch
- Tropical floral print
- Sleeveless V-neckline
- Metal flower hardware accent, keyhole cutout
- Tie-back halter spaghetti straps, partially open back
- Maxi-length hem, form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-000464
Category Name: Casual Dresses
Price: $44.90
Availability: In Stock
Available Color: ORANGE
Available Size: XS, S, M, L
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Bare It All Open Back Bodycon Midi Dress
Clean lines, confident fit, no extra effort required. This ribbed midi dress keeps things sleek and minimal with a body-hugging silhouette that feels just as good as it looks. Perfect for dressing up or down.
Fit & Features
- Soft ribbed knit fabric with comfortable stretch
- Square neckline with slim spaghetti straps
- Sleeveless bodycon silhouette
- Low open back design
- Midi length that hits below the knee
- Runs true to size
Style Number/Barcode: 05102-000467
Category Name: Casual Dresses
Price: $39.90
Availability: In Stock
Available Color: BLACK
Available Size: XS, S, M, L, XL
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Wrapped In Charm Off-Shoulder Mini Dress
This mini dress is that perfect mix of soft and sculpted—the one you reach for when you want to look undone in a chic way. The foldover off-shoulder neckline adds a flirty twist, while the rib knit hugs you with just the right amount of confidence.
Fit & Features
- Soft rib knit fabric with stretch
- Foldover off-shoulder neckline with subtle twist detail
- Fitted long sleeves
- Bodycon silhouette
- Mini length hem
- Runs true to size
Style Number/Barcode: 05102-000469
Category Name: Casual Dresses
Price: $9.97 $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: S, M, L
Product Badge:- Back In Stock