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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Let's Go Party Marble Mesh Mini Dress
You'll be ready to live it up this festival season in this trendy marble mesh mini dress! It features a sleeveless square neckline, spaghetti straps, an alluring open back with a lace-up strappy design, a mini-length hem with a curve-hugging bodycon silhouette, and a fab marble swirl printed design. The lined mesh fabric offers plenty of stretch. Complete your party look with a faux leather jacket.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, lace-up strappy design, tie closure
- Mini-length hem, bodycon silhouette
- Marble swirl print
- Sheer mesh fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4960
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Just Peachy Keen Off-The-Shoulder Midi Dress
Look and feel peachy keen in this cute swiss dot midi dress perfect for strolls downtown or grabbing brunch! It features an off-the-shoulder neckline with adorable flutter short-sleeve cuffs, a stretchy smocked bodice, and a flowy hem with a front-slit accent. Complete the look in sleek hoop earrings and sandals.
Fit & Features
- Off-the-shoulder neckline
- Flutter short-sleeve cuffs
- Stretchy smocked bodice
- Flowy midi-length hem, front slit accent
- Swiss dot woven fabric, mini-length woven lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4953
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Mart Chiffon Skater Dress
Always look like you've just come from somewhere with flowers! This breezy ditsy floral skater dress embodies every girl's favorite thing about spring. It features sheer 3/4 length sleeves with elastic cuffs, a sweetheart neck with a bust tie and keyhole, a smocked back, and a flowy fit and flare short-length hem. Complete the look in platform wedges.
Fit & Features
- Sheer 3/4 length sleeves, elastic cuffs
- Sweetheart neck, bust tie, and keyhole
- Smocked back
- Skater silhouette, short-length hem
- Ditsy floral print
- Chiffon fabric with lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-2161
Category Name: Casual Dresses
Price: $10.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Pretty Chiffon Midi Dress
Showcase your effortless beauty in this airy, lightweight chiffon midi dress. It features a sweetheart neckline with a ruched bodice, long sheer peasant sleeves, a stretchy smocked back design, a fitted high waist seam, a midi-length hem with a high front slit, and a flowy, A-line silhouette. Style with clear mules for a weekend brunch date.
Fit & Features
- Sweetheart neckline, ruched bodice
- Long sheer peasant sleeves, elastic cinched hems
- Stretchy smocked back design
- Fitted high waist seam
- Midi-length hem, high front slit, A-line silhouette
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4954
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flower Power Lace-Up Mini Dress
Keep your spring look on point with this cute and casual floral mini dress! It features a sleeveless scoop neckline, spaghetti straps, a lace-up back with tie closure, a bodycon silhouette, and a charming flower print on stretchy knit fabric. Complete the look with sandals for a day date!
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back with tie closure
- Bodycon silhouette, mini-length hem
- Flower print
- Lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4955
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Spirit Chiffon Skater Dress
Play up your flirty side in this adorable chiffon skater dress featuring sheer peasant sleeves, a square neckline, an open-back with tie closure, and a short-length hem. Complete the look in platform heels for a dressy event!
Fit & Features
- Sheer peasant sleeves
- Square neckline
- Open-back with tie closure
- Skater silhouette
- Short-length hem
- Airy chiffon fabric, woven lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-2162
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Surprise Color Block Dress
Mix it up this season! Step out in this trendy color block mini dress featuring fitted long sleeves, a scoop neck, and a bodycon silhouette on stretchy rib-knit fabric. Style with over-the-knee boots to complete the look!
Fit & Features
- Fitted long sleeves
- Scoop neck
- Bodycon silhouette
- Mini-length hem
- Color block pattern
- Rib-knit fabric, double-lined, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4952
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pick Me Floral Lace-Up Maxi Dress
This floral maxi dress will be the first pick in your closet! It features a sleeveless V-neckline with a knotted bust, spaghetti straps that creates the open lace-up back design, and a flowy slim silhouette. Complete the look in cute new sandals for a baby shower or casual lunch out!
Fit & Features
- Sleeveless V-neckline, knotted bust
- Spaghetti straps
- Lace-up open back
- Flowy slim silhouette
- Maxi-length hem
- Floral print, breezy woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4947
Category Name: Casual Dresses
Price: $5.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Slay Tropical Print Midi Dress
Slay your vacay look with this curve-hugging tropical print midi dress! It features a sleeveless V-neckline, spaghetti straps, a ruched side seam, a midi-length asymmetric hem creating a chic side slit, and a bodycon silhouette. The all-over tropical palm leaf print will really bring those vacay vibes. Complete the look with clear mules.
Fit & Features
- Sleeveless V-neckline, spaghetti straps, bust lining
- Ruched side seam
- Midi-length asymmetric hem, side slit
- Bodycon silhouette
- Tropical palm leaf print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4948
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Made You Flirt Lace Skater Dress
Make your crush flirt with how cute you'll be looking in this lace eyelet short dress perfect for birthday brunches or parties! Featuring a sleeveless scoop neck, ruffled straps, a ruched bust, and a fit-and-flare skater silhouette. Style with a chic bracelet and heels to complete the look.
Fit & Features
- Sleeveless scoop neck, ruffled straps
- Ruched bust
- Fit and flare skater silhouette
- Short-length hem
- Lace eyelet fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05101-2155
Category Name: Casual Dresses
Price: $5.97 $44.90
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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Butterfly Kisses Rhinestone Mini Dress
Every heart will flutter with your winged beauty! This rib knit mini dress features a sleeveless scoop neck, spaghetti straps, a rhinestone butterfly design, and a bodycon silhouette. Complete the look in cute sandals for a casual party or lunch!
Fit & Features
- Sleeveless scoop neck
- Spaghetti straps
- Rhinestone butterfly design
- Bodycon silhouette
- Mini-length hem
- Soft rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4944
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Meadow Vibes Floral Eyelet Lace Mini Dress
Give your closet a dreamy meadow vibe with this floral mini dress - an adorable option for brunch and day dates! Featuring puff short sleeves, a sweetheart neck, front bust tie, and side ruched seam to accentuate your curves along the bodycon silhouette. The dress is composed of a ditsy daisy print on eyelet lace fabric with a stretchy knit lining. Complete the look in strappy sandals.
Fit & Features
- Puff short sleeves
- Sweetheart neck, front bust tie
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Ditsy daisy print
- Eyelet lace, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4945
Category Name: Casual Dresses
Price: $5.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Infatuated Floral Satin Midi Dress
Spark everyones infatuation for you in this floral midi dress - a sultry style for wedding showers, graduations, and outdoor parties! The dress features a sleeveless cowl neckline, adjustable spaghetti straps, and a slim curve-hugging silhouette. Complete the look with a clutch and mules.
Fit & Features
- Sleeveless cowl neckline
- Adjustable spaghetti straps
- Slim, curve-hugging silhouette
- Midi-length hem
- Vintage rose floral print
- Silky smooth satin, no stretch
- Runs true to size
Style Number/Barcode: 05102-4942
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Natural Attraction Ditsy Floral Mini Dress
You're sure to have a natural attraction to this ditsy floral mini dress - perfect for a casual birthday or afternoon tea! It features a sleeveless scoop neck, spaghetti straps, a flirty tie front, and ruched bust, and a bodycon silhouette. Style with lace-up heels for a statement finish!
Fit & Features
- Sleeveless scoop neck
- Spaghetti straps
- Tie front and ruched bust
- Bodycon silhouette
- Mini-length hem
- Ditsy floral print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4938
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fresh In Paisley Floral A-Line Dress
Serve your closet a fresh style by adding this paisley floral short dress to it! Featuring a sleeveless V-neckline, sleek bungee spaghetti straps, a flattering A-line silhouette, and a flirty slit hem. Complete the look in trendy sandals for an afternoon in the city!
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- A-line silhouette
- Short-length hem, slit accent
- Paisley floral print
- Smooth stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-4943
Category Name: Casual Dresses
Price: $5.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Staple Long Sleeve Midi Dress
This long sleeve midi dress is such a stylish staple! Featuring a square neckline with a chic center cutout at the bust, long fitted sleeves, a midi-length hem with a front slit, and a form-hugging fit, this crepe dress can be styled up or down. Pair with strappy mules for a date night.
Fit & Features
- Square neckline
- Small bust cutout
- Long fitted sleeves
- Midi-length hem, front slit
- Form-hugging fit
- Crepe fabric, short knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5529
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romantic Roots Floral Chiffon Short Dress
Get back to your romantic roots this season in this breezy ditsy floral chiffon dress perfect for baby showers to Sunday brunch! It features a sleeveless V-neck with a flirty bust tie, adjustable spaghetti straps, a stretchy smocked back, and a flattering skater short-length silhouette. Complete the look in strappy espadrille wedges.
Fit & Features
- Sleeveless V-neck, bust tie, adjustable spaghetti straps
- Stretchy smocked back, padded bust
- Skater silhouette
- Short-length hem
- Ditsy floral print
- Chiffon fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-4939
Category Name: Casual Dresses
Price: $9.97 $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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Cute And Casual Everyday Ribbed Knit Midi Dress
This ribbed knit midi dress is cute, casual, and perf for everyday styling! It features a sleeveless V-neckline, spaghetti straps, a midi-length hem with a side slit accent, and a form-hugging silhouette. The ribbed knit fabric offers plenty of stretch. Pair with a cropped denim jacket and strappy mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-4934
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sunny Days Floral Chiffon Skater Dress
Swing into the sunnier days ahead in this floral chiffon dress! It features a sleeveless square neck, adjustable spaghetti straps, a stretchy smocked bodice, and a tiered ruffle short-length skater silhouette. Complete the look in cute espadrille wedges for a family picnic!
Fit & Features
- Sleeveless square neck, adjustable spaghetti straps
- Stretchy smocked bodice
- Skater silhouette, tiered ruffles
- Short-length hem
- Floral print, airy chiffon, knit lining
- Runs true to size
Style Number/Barcode: 05102-4936
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out Of Office Tropical Print Maxi Dress
Packing this gorgeous tropical print maxi dress in your carry-on is a must for your vacay getaway! It features a sleeveless V-neckline with an O-ring accent at the bust, a sultry waist cutout at the front, adjustable spaghetti straps, a fitted, flowy, floor-length hem, and a thigh-high front slit. The smooth knit fabric showcases a tropical palm leaf print. Style with cute wedges.
Fit & Features
- Sleeveless V-neckline, center O-ring bust accent
- Front waist cutout
- Adjustable spaghetti straps
- Fitted, flowy, floor-length hem, high front slit
- Tropical palm leaf print
- Knit fabric, short-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5015
Category Name: Casual Dresses
Price: $9.97 $43.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacation Awaits Tropical Print Cutout Maxi Dress
Be sure to pack this bold tropical print maxi dress in your carry-on for your next warm-weather vacay! It features a sleeveless V-neckline with a twist-front design at the bust, a sultry waist cutout at the front, adjustable spaghetti straps, a floor-length hem with a thigh-high front slit, and a flowy A-line silhouette. The smooth and stretchy knit fabric features an all-over tropical palm leaf print for an island vibe. Style with strappy sandals.
Fit & Features
- Sleeveless V-neckline, twist-front design
- Front waist cutout
- Adjustable spaghetti straps
- Floor-length hem, high front slit
- Flowy A-line silhouette
- Tropical palm leaf print
- Knit fabric, mini-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4928
Category Name: Casual Dresses
Price: $5.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale