Casual Dresses
Casual dresses that keep up with your plans—brunch, game day, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and sweater knits, these pieces prove laid-back can still look styled. Play it polished with a shirt dress or belted A-line, lean comfy-cute in a fitted bodycon, 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 outing, these casual dresses are built to move with your mood—and your calendar.
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STYLE SPOTLIGHT
Discover New Skater Dress Styles
Everyday Ease: Casual Dresses for Cool-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.
Laid-Back & Versatile
Knit, ribbed, and sweater dresses bring comfort and style to crisp fall 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 burgundy 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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Cue The Charm Linen Off-The-Shoulder Dress
This linen skater dress cues the charm you'll be bringing to wine tasting with the ladies or a birthday brunch! It features a cute off-the-shoulder ruffle trim neckline with elasticized short-sleeve cuffs, a tie-waist belt, and a flattering short-length tiered ruffle hem. Complete the look with a dainty tennis bracelet and sandals.
Fit & Features
- Off-the-shoulder ruffle trim neckline
- Elasticized short-sleeve cuffs
- Back zipper and hook-eye closure
- Tie-waist belt
- Skater silhouette, short-length tiered ruffle hem
- Linen fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2341
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She Knows Style Eyelet Lace Skater Dress
Breeze into every occasion in this stylish eyelet lace skater dress! It features a sleeveless square neck, spaghetti straps, a ruched bust, and a flattering fit and flare short-length hem. The sheer eyelet lace fabric includes a full knit lining and offers plenty of stretch. Complete the look with statement block heels for a wedding shower or birthday lunch!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Ruched bust
- Fit and flare, skater silhouette
- Short-length hem
- Sheer eyelet lace fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4998
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy Looks Mesh V-Neck Babydoll Dress
Showcase a dreamy look in this mesh babydoll dress perfect for date nights or parties! It features a sleeveless V-neckline, adjustable spaghetti straps, ruched bust seams, and a flattering babydoll style silhouette with a mini-length hem. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Ruched bust seams
- Babydoll style silhouette
- Mini-length hem
- Airy mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4971
Category Name: Casual Dresses
Price: $5.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paint Me In Floral V-Neck Maxi Dress
This floral maxi dress will fit like a dream and give off major artsy vibes! It features a sleeveless V-neckline, spaghetti straps, a hip-hugging fit, and a sultry front slit along the flowy hem. Complete the look in dainty earrings for a daytime soiree!
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Hip-hugging fit
- Front slit, flowy maxi-length hem
- Floral watercolor print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5018
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Party Starter Studded Denim Mini Tube Dress
Your weekend lineup just found its headliner—this denim mini tube dress nails the mix of edgy and glam. The studded detailing adds that bold pop, while the bodycon fit keeps it extra sleek.
Fit & Features
- Denim fabric
- Strapless straight-across neckline
- Seam detailing, studded trim accents
- Back zipper closure
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000260
Category Name: Casual Dresses
Price: $46.90
Availability: In Stock
Available Color: DENIM
Available Size: XS, S, M, L
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Vacay In Bali One-Shoulder Maxi Dress
Vacation in sultry style wearing this maxi dress! Serve major looks on the island in this dress featuring a sleeveless one-shoulder neckline, a tank strap with a hoop insert, and a form-hugging slim silhouette with a high side slit and ruched seam on textured knit fabric. Complete the look in chic sandals.
Fit & Features
- Sleeveless one-shoulder neckline
- Tank strap, hoop insert
- Form-hugging, slim silhouette
- High side slit, side ruched seam
- Maxi-length hem
- Textured knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4970
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Modern Marvel One-Shoulder Mini Dress
Strut looking like a modern work of art in this marble-printed mini dress all over town! It features a sleeveless one-shoulder neck, an adjustable spaghetti strap, a side adjustable ruched string, and a bodycon silhouette. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neck
- Adjustable spaghetti straps
- Side ruched string
- Bodycon silhouette
- Mini-length hem
- Marble-printed mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4989
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What A Sight Eyelet Lace Lace-Up Dress
You'll be quite a dreamy sight in this eyelet lace skater dress! Perfect for wedding showers, grabbing lunch with the girls, or backyard parties. It features adorable puff short sleeves, a sweetheart neck with an underbust seam, an open lace-up back, and a flattering short-length silhouette. Complete the look in strappy block heels.
Fit & Features
- Puff short sleeves
- Sweetheart neck, underbust seam
- Open lace-up back
- Skater silhouette
- Short-length hem
- Eyelet lace cotton fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4946
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lovely Seeing You Floral Chiffon Midi Dress
They'll be pleased to make your lovely acquaintance looking so romantic in this floral chiffon midi dress as the perfect wedding guest! The sleeveless dress features a sweetheart neckline, adjustable spaghetti straps, a stretchy smocked back, a built-in padded bust, and a flattering front slit along the flowy hem. Complete the look with clear lucite block heels and a clutch.
Fit & Features
- Sleeveless sweetheart neckline
- Adjustable spaghetti straps
- Stretchy smocked back, zipper and hook-eye closure
- Built-in padded bust
- Front slit, midi-length hem
- Garden rose print, airy chiffon, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2214
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Darling Eyelet Lace V-Neck Dress
You'll be everyone's favorite sight looking so darling in this eyelet lace dress at dinner parties! It features a sleeveless V-neckline, wide shoulder straps, a stretchy smocked back, and a flattering tiered skater short-length silhouette. Complete the look with a charming rhinestone barrette for a chic hairstyle!
Fit & Features
- Sleeveless V-neckline
- Wide shoulder straps
- Stretchy smocked back
- Tiered, skater short-length silhouette
- Eyelet lace fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2030
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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True Romance Floral Chiffon Lace Dress
Fall for this floral chiffon dress to add romance this season! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an lovely lace back with a lower cutout, and a flattering skater short-length silhouette. Complete the look with a dainty ring set.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Lace back, lower cutout
- Skater silhouette
- Tiered short-length hem
- Floral watercolor print
- Airy chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-2220
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sippin' On Sultry Off The Shoulder Maxi Dress
Strut your sultry self in this off-the-shoulder maxi dress for sipping on cocktails at sunset! It features a strapless neckline, fitted long sleeves, a bodycon silhouette, and a high-side slit along the hem. The dress is composed of a slinky knit and stretchy fabric. Complete the look with block heels.
Fit & Features
- Strapless neckline
- Off-the-shoulder
- Fitted long sleeves
- High-side slit
- Maxi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5124
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oh-So-Sweet Puff Sleeve Mini Dress
Create an oh-so-sweet look in this darling puff sleeve mini dress! It features a square neckline, short puff sleeves, an open-back design with bar straps, a mini-length hem, and a form-hugging fit for a figure-flattering silhouette. The crepe fabric offers a moderate stretch. Style with clear heels for a dinner date.
Fit & Features
- Square neckline
- Short puff sleeves, elastic cinched hems
- Open-back design, dual elasticized bar straps
- Mini-length hem
- Form-hugging fit
- Crepe fabric, knit lining at the bust, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2098
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Iconic Basic Cap Sleeve Midi Dress
An iconic basic midi dress your closet needs! Create effortlessly chic looks with this knit dress featuring cap sleeves, a V-neck, and a bodycon silhouette with a curved hemline on brushed stretchy fabric. Style with slide sandals and sunglasses for hanging downtown with friends!
Fit & Features
- Cap sleeves
- V-neck
- Bodycon silhouette
- Curved midi-length hemline
- Brushed stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05101-2530
Category Name: Casual Dresses
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh Perspective Eyelet Lace Skater Dress
This eyelet lace cotton skater dress will give you a fresh perspective for creating a spring wardrobe! It features a sleeveless V-neckline, adjustable spaghetti straps, a flirty tie-back design, and a flattering fit and flare short-length silhouette. Complete the look in cute sandals for brunch or wine tasting!
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Tie-back design
- Fit and flare, skater silhouette
- Short-length hem
- Eyelet lace cotton fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4886
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute Factor Eyelet Lace Skater Dress
Bring the cute factor by wearing this eyelet lace skater dress for picnics, brunch, or casual family parties! Featuring adorable puff short sleeves, a square neck with a ruched bust, a flirty tie-back closure, and a fit-and-flare silhouette and short hem. Complete the look with cute flower earrings.
Fit & Features
- Puff short sleeves
- Square neck, ruched bust
- Tie-back closure
- Skater, fit and flare silhouette
- Short-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4910
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh Breeze Floral Chiffon Midi Dress
Freshen up your wardrobe for spring to summer with this floral chiffon midi dress - a lovely style for wedding showers and birthday brunches! It features adorable puff short sleeves, a square neck, a flirty bust tie and underbust seam detail, and a slim-fit silhouette with a front slit hem. The airy chiffon fabric features a bouquet floral print pattern. Complete the look with dainty hoop earrings.
Fit & Features
- Puff short sleeves, elastic cinched hems
- Square neck, bust tie, underbust seam detail
- Back zipper, hook and eye closure
- Slim-fit silhouette, front slit, midi-length hem
- Bouquet floral print
- Sheer chiffon fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2130
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Touch Crepe Daisy Print Short Dress
Add a playful touch to your closet with this adorable crepe daisy print dress to wear for birthdays or family parties! It features puff short sleeves, a sweetheart neckline, a flirty bust tie, a stretchy smocked back, hidden side pockets for keeping your hands warm, and a tiered ruffled short-length hem. Complete the look with dainty earrings.
Fit & Features
- Puff short sleeves
- Sweetheart neckline
- Bust tie front, stretchy smocked back
- Hidden side pockets
- Tiered ruffled short-length hem
- Daisy print,
Style Number/Barcode: 05101-2338
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Subtle Love Ditsy Floral Mini Dress
Effortlessly cute with subtle detail, what's not to love about this ditsy floral mini dress? It features a sleeveless V-neckline with a ruched bust seam, spaghetti straps, and a bodycon silhouette. Complete the look in trendy flat sandals for a brunch.
Fit & Features
- Sleeveless V-neckline, ruched bust seam
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print
- Ribbed stretchy knit fabric, knit lining
- Runs true to size
Style Number/Barcode: 05102-5073
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serving Looks Mock Neck Ponte Mini Dress
Not your average court-side fit. This contrast-trim mini dress serves preppy energy with a flirty twist—perfect for brunch, errands, or wherever the vibe is “cute but casual.”
Fit & Features
- Contrast-trim, smooth ponte knit fabric with stretch
- Mock neckline
- Keyhole cutout with button closure
- A-Line silhouette
- Front slit accent
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000205
Category Name: Casual Dresses
Price: $35.90
Availability: In Stock
Available Color: BLACK
Available Size: S, M, L
Product Badge:- Back In Stock
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The Cutest Denim V-Neck Mini Dress
Show off your cute figure in this stylish denim mini-dress! It features a sleeveless sweetheart neck, wide shoulder straps, a front exposed zipper closure, and a bodycon silhouette. Complete the look in lace-up heels for a birthday party!
Fit & Features
- Sleeveless sweetheart neck
- Wide shoulder straps
- Front exposed zipper closure
- Bodycon silhouette
- Mini-length hem
- Denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-4591
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tending The Blooms Floral Midi Dress
This floral midi dress needs no gardening skills to keep beautiful! It features a sleeveless cowl neckline, spaghetti straps, a form-hugging silhouette, and a flirty front slit. Complete the look in whimsical butterfly earrings for a garden party!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Form-hugging silhouette
- Front slit
- Midi-length hem
- Garden floral print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05101-1684
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Modern Romance Eyelet Lace Mini Dress
A modern take on a romantic silhouette! This eyelet lace mini dress is cute for bridal showers or casual day dates. It features long peasant sleeves, a square neck, a ruched bust, and a form-hugging silhouette. Complete the look in chic lucite block heels.
Fit & Features
- Long peasant sleeves
- Square neck, ruched bust
- Form-hugging silhouette
- Mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4941
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Can't Resist Chiffon Floral Skater Dress
No one can resist you in this chiffon floral dress - a staple for all of the upcoming soirees! It features a sleeveless V-neckline, adjustable spaghetti straps, a tie-back closure, and a flattering skater short silhouette. Complete the look in faux leather mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Tie-back closure
- Skater silhouette
- Short-length hem
- Floral print, chiffon fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05101-2057
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale