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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Casual Dresses Made for Everyday Fall Plans
Windsor’s casual dresses make everyday styling easy with comfortable fabrics, relaxed silhouettes, and trend-right details for workdays, weekends, and everything in between. From breezy cotton and linen-blend day dresses to colored denim, playful prints, and cozy seasonal layers, these one-and-done looks help you feel polished without overthinking the outfit.
Easy Prints, Textures & Layers for the Season
Give your everyday dresses a fall refresh with polka dots, stripes, gingham, ditsy florals, and colored denim that add personality without making styling complicated. When temperatures dip, explore sweater dresses for an easy cozy layer that works with boots, jackets, and cold-weather accessories.
What Makes a Dress Casual?
A casual dress combines comfortable fabrication, an easy-to-wear silhouette, and details that fit naturally into everyday plans. Cotton and linen blends feel breathable and relaxed, while uncomplicated prints and laid-back shapes make getting dressed quick. The best casual dresses also leave room to change the vibe with your shoes, layers, and accessories instead of requiring a completely new outfit.
How Do You Transition a Casual Dress From Summer to Fall?
Start with a lightweight dress you already love, then add pieces that bring warmth without weighing down the look. Style a ditsy floral dress or plaid mini with ankle boots and a cardigan, or layer a colored denim dress with a fitted long sleeve as cooler weather arrives. Switching warm-weather sandals for boots and adding a jacket lets your favorite day dresses stay in rotation longer.
Which Fabrics Work Best for Everyday Dresses?
Think about comfort, movement, and the weather ahead. Cotton and linen blends are breathable choices for warmer transitional days, while knits add softness and extra warmth as fall turns to winter. On colder days, pair knit everyday dresses with tights, tall boots, and a coat for an easy outfit that feels cozy while still looking put together.
How Can You Style One Casual Dress for Different Plans?
Start simple and let your layers and accessories switch up the vibe. Wear a casual midi or skater dress with sneakers and a crossbody bag for daytime plans, then add ankle boots, jewelry, and a Windsor belt when dinner gets added to the group chat. An adjustable belt can define your waist, dress up a laid-back look, or layer with other belts for a more statement-making finish—and it works just as easily over dresses, tops, and jackets. Want more ways to remix your everyday looks? Discover how to blend relaxed pieces with statement details in Windsor’s sporty chic style guide. When winter arrives, add tights, tall boots, a cozy cardigan, or a polished coat for extra warmth. That day-to-evening and season-to-season flexibility is what makes casual dresses a closet favorite for fall and winter.
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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: $7.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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
- Black has 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: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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