Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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Text Me Later Strappy Back Mini Dress
Their text can wait. You'll be too busy catching all the attention in this casual mini dress featuring a sleeveless square neck, bungee spaghetti straps, a strappy open-back, and a bodycon silhouette. The dress is composed of a texture knit fabric with a stretchy lining. Complete the look in a crop denim jacket.
Fit & Features
- Sleeveless square neck
- Bungee spaghetti straps
- Strappy open back
- Bodycon silhouette
- Mini-length hem
- Texture knit fabric, stretchy lining
- Runs true to size
Style Number/Barcode: 05102-4981
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swing My Way Eyelet Lace Midi Dress
This eyelet lace midi dress is sure to get your crush's attention! It features a sleeveless V-neckline, adjustable spaghetti straps, button front accents, a flattering A-line silhouette, and a front slit along the hem. Complete the look in clear block heels for a daytime soiree!
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Button front accents
- A-line silhouette
- Front slit, midi-length hem
- Eyelet lace fabric, partial woven lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4982
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Perfection Ribbed Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Square neckline
- Long fitted bell sleeves, flared hems
- Mini-length hem, form-hugging fit
- Ribbed knit fabric, knit lining, plenty of stretch
- Style runs small
Style Number/Barcode: 05102-5217
Category Name: Casual Dresses
Price: $5.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dreamy In Floral Satin Midi Dress
Create a dreamy look in this floral satin midi dress for brunch or bridal showers! It features a sleeveless cowl neckline, adjustable spaghetti straps, a curve-hugging slim silhouette, and a flirty side slit accent. Complete the look in heeled mules.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Curve-hugging, slim silhouette
- Side slit accent
- Midi-length hem
- Floral print, silky satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4985
Category Name: Casual Dresses
Price: $19.97 $44.90
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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Trip To The Tropics Printed Midi Dress
You'll look like you're ready to whisk away on a tropical vacay in this printed midi dress! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem, a hip-hugging fit and an A-line silhouette, a thigh-high front slit, and an eye-catching tropical palm leaf print. Style with trendy wedges.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, hip-hugging fit, A-line silhouette
- High front slit
- Tropical palm leaf print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4979
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Garden Chic Floral Chiffon Midi Dress
Enchanting and chic, this floral chiffon midi dress is perfect for a garden wedding. It features a sleeveless sweetheart neckline with a bust outline, adjustable spaghetti straps, a high waist seam, a smocked back panel with a zipper closure, a midi-length hem with a high front slit, and a flowy A-line silhouette. The airy chiffon fabric features a romantic blooming floral print alongside a dainty flower pattern. Style with clear block heels.
Fit & Features
- Sleeveless sweetheart neckline, padded bust and outline
- Adjustable spaghetti straps
- High waist seam, stretchy smocked back, zipper and hook-eye closure
- Midi-length hem
- Front slit, A-line silhouette
- Floral print, chiffon fabric, smooth stretchy knit lining
- Style runs small
Style Number/Barcode: 05101-2212
Category Name: Casual Dresses
Price: $20.97 $45.90
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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Extra Flair Floral Skater Dress
You'll be a darling delight in this short skater dress perfect for parties and ceremonies! It features three-quarter-length puff sleeves, a square neck, a smocked back, and a fit and flare silhouette. The dress is composed of a floral burnout woven fabric with a chiffon lining and no stretch. Style with earrings and a choker to complete the look!
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Smocked back
- Fit and flare skater silhouette
- Short-length hem
- Floral burnout woven fabric, chiffon lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2211
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everlasting Pretty Floral Chiffon Skater Dress
Freshen up your closet in this pretty floral chiffon dress for a blissful day date to jaunt through a garden party! It features sheer peasant long sleeves, a smocked and stretchy V-neck bodice, a fit and flare silhouette, and a flowy short-length hem. The dress is designed with a gorgeous floral pattern on airy chiffon with a stretchy knit lining. Complete the look with strappy platform heels.
Fit & Features
- Sheer peasant long sleeves
- Smocked and stretchy V-neck bodice
- Back zipper closure
- Skater silhouette
- Flowy short-length hem
- Floral pattern, chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4977
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Queen Tropical Floral Midi Dress
Slay in all of your vacation pics like the stylish queen you are in this tropical floral midi dress! It features a sleeveless square neckline, spaghetti straps, a midi-length hem, a bodycon silhouette that will hug your curves, and a bold tropical floral print pattern. The sheer mesh fabric includes a stretch knit lining. Complete the look with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Midi-length hem
- Bodycon silhouette
- Tropical floral print
- Sheer mesh fabric, stretch knit lining
- Runs true to size
Style Number/Barcode: 05102-4980
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Friendly Flirt Eyelet Mini Dress
Catch yourself a cutie-looking flirty in this eyelet mini dress featuring short puff sleeves, a sweetheart neck, a ruched bust with a tie front, a corset-seam bodice, and a bodycon silhouette. The dress is composed of stretchy eyelet lace fabric with a knit lining. Complete the look with a dainty choker and earrings set.
Fit & Features
- Short puff sleeves
- Sweetheart neck
- Ruched bust, tie front
- Corset-seam bodice
- Bodycon silhouette, mini-length hem
- Eyelet lace, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4978
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just Spotted Leopard Lace-Up Midi Dress
Just spotted, you in this effortlessly fierce leopard print midi dress! It features a sleeveless V-neckline with a twisted bust accent, spaghetti straps that lace up in the back, and a flattering A-line silhouette with a flowy hem. Complete the look with a sleek choker for lunch with friends!
Fit & Features
- Sleeveless V-neckline, twisted bust accent
- Spaghetti straps, lace-up back
- A-line silhouette
- Flowy midi-length hem
- Leopard print, breezy woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4976
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Style Eyelet Knit Mini Dress
Show off the sweetest style in this adorable eyelet knit mini dress. It features a sleeveless sweetheart neckline with a knot-front design at the bust, spaghetti straps, a mini-length hem, a form-hugging fit, and a dainty floral eyelet pattern. The lined knit fabric offers plenty of stretch. Complete your look with espadrille sandals for a weekend date.
Fit & Features
- Sleeveless sweetheart neckline, knot-front design
- Spaghetti straps
- Mini-length hem
- Form-hugging fit
- Floral eyelet pattern
- Lined knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4969
Category Name: Casual Dresses
Price: $5.97 $34.90
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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Looking Like A Day Dream Eyelet Lace Dress
Look like a daydream come true in this eyelet lace mini dress for your next date! It features adorable puff sleeves with ruffle trim, a sweetheart neck, a ruched bust seam, and a bodycon silhouette with a flirty tiered ruffle hem. Complete the look in cute stiletto heels.
Fit & Features
- Puff short sleeves, ruffle trim
- Sweetheart neck
- Ruched bust seam
- Bodycon silhouette
- Tiered ruffle mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2184
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Language Of Romance Lace Babydoll Dress
This lace babydoll dress speaks your language for romance! Let this short dress sweep you off your feet for wedding showers, graduations, or birthday brunches! It features three-quarter-length puff sleeves, a square neck, a stretchy smocked back, and an empire waist seam that flares out into the flowy hem. Complete the look in new sandals and a clutch!
Fit & Features
- Three-quarter-length puff sleeves
- Square neck
- Stretchy smocked back
- Empire waist, fit and flare silhouette
- Flowy short-length hem
- Lace overlay, chiffon lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4973
Category Name: Casual Dresses
Price: $5.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Somewhere Tropical V-Neck Midi Dress
You deserve to go somewhere tropical with this midi dress as your inspiration! It features a sleeveless V-neckline, spaghetti straps, a curve-hugging silhouette, and a flirty slit hem. The dress is composed of a palm-printed stretchy knit fabric. Complete the look in strappy-heeled sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Curve-hugging silhouette
- Slit midi-length hem
- Palm print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4966
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flowy Feels Paisley Maxi Dress
You'll love the flowy fit of this paisley maxi dress, perfect for the warmer months! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem, and a thigh-high front slit. The smooth and stretchy knit fabric features a trendy paisley print pattern. Complete the look with strappy sandals.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Maxi-length hem, high front slit
- Flowy silhouette
- Paisley print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4967
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiercely Stylish Leopard Print Maxi Dress
Keep it fiercely stylish with a maxi dress that brings a chic flair! The lightweight knit dress features a sleeveless V-neckline, spaghetti straps, a maxi-length, flowy, A-line silhouette, a sultry thigh-high front slit, and a trendy leopard print pattern. Complete the look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Maxi-length A-line silhouette
- High front slit
- Leopard print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4968
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Dream Escape Tropical Midi Dress
Pack right for your dream escape with this tropical print midi dress perfect for a dinner with a beachside view! It features a sleeveless V-neckline, adjustable spaghetti straps that crisscross in the back, a bodycon fit, and a ruched side seam to accentuate your curves atop a sultry slit. The smooth knit fabric features a gorgeous tropical floral print that will give off major vacay vibes. Complete the look with sleek earrings and a choker necklace.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, crisscross back
- Bodycon silhouette
- Side ruched seam, slit accent
- Asymmetric midi-length hem
- Tropical floral print, knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4957
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Palms Tropical One-Shoulder Dress
This tropical mini dress will put you in vacay mode! Flaunt some skin in this sleeveless one-shoulder dress featuring a sleek bungee spaghetti strap, side ruched seams to accentuate your curves, and a bodycon fit. The dress is designed with a palm leaf print on stretchy knit-lined fabric. Complete your getaway look in platform wedges.
Fit & Features
- Sleeveless one-shoulder neckline
- Bungee spaghetti strap
- Side ruched seams
- Bodycon fit, mini-length hem
- Palm leaf print
- Lined stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4956
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Prowlin' Cutie Leopard Crepe A-Line Dress
Look cute for your daytime prowls in this leopard print crepe dress! It features long bell sleeves, a scoop neck with a ruched tie-front bust, halter straps with self-tie closure, and a flattering A-line silhouette and dual side slit accents. Complete the look in sassy sandals!
Fit & Features
- Long bell sleeves
- Scoop neck, ruched tie-front bust
- Halter straps, self-tie closure
- A-line silhouette
- Short-length hem with dual side slit accents
- Leopard print, crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4959
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale