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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Adoring Cutie Sleeveless Lace-Up A-Line Mini Dress
An attention-worthy A-line mini dress that'll have everyone adoring your cuteness! This square neck dress accentuates your curves while the lace-up back adds a touch of playfulness. The A-line silhouette and mini-length hem are perfect for any occasion. Complete the look in wedges and a clutch!
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Spagehtti straps
- Square neckline
- Lace-up
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5689
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Artsy Flair Strapless Cutout Abstract Mini Dress
Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.
Fit & Features
- Abstract print, mesh fabric, stretchy knit lining
- Strapless neckline
- Side cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5693
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out Of Office One Shoulder Tropical Maxi Dress
This tropical maxi dress says it's time for vacation! Switch your email to out of office and enjoy a sunny destination in this sleeveless dress featuring a one-shoulder neckline adorned with a knotted shoulder strap, a flattering mermaid silhouette, and a maxi-length hem. Complete the look with sunglasses and a cocktail in hand!
Fit & Features
- Tropical palm leaf print, stretchy knit fabric
- One-shoulder neckline
- Knotted shoulder strap
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5695
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Paradise Pick V-Neck Cutout Tropical Maxi Dress
Enjoy the fun and sun on your paradise vacay in this tropical maxi dress! This flowy maxi silhouette features adjustable spaghetti straps, a flirty V-neckline with a keyhole, and a sultry cutout back. With a front slit, you'll steal the show with every step. Complete the look with sunnies and a straw handbag.
Fit & Features
- Tropical print, mesh fabric lined with stretchy knit
- Adjustable spaghetti straps
- V-neckline, keyhole
- Cutout back
- Front slit
- Flowy maxi silhouette
- Runs true to size
Style Number/Barcode: 05102-5692
Category Name: Casual Dresses
Price: $24.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Style Cowl Neck Slit Paisley Maxi Dress
Bask in the aesthetic perfection of this paisley mesh maxi dress whether you're on vacation or having a sunset dinner with friends! This form-hugging dress features a cowl neckline and spaghetti straps, highlighting your figure in all the right ways. The high-side slit and sheer maxi-length hem add a touch of allure to this must-have dress! Complete the look with a necklace and earrings.
Fit & Features
- Paisley print, partially lined mesh fabric
- Cowl neckline
- Spaghetti straps
- High side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5694
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunshine And Good Time V-Neck Mermaid Maxi Dress
This mermaid maxi dress is here for sunshine and good times! Made from textured mesh fabric, this dress will have you feeling so cute. Features a flattering V-neckline, dual spaghetti straps, a crisscross back, and a bust cutout. The mermaid silhouette and high front slit accentuate your curves, while the maxi-length hem adds a touch of chicness. Complete the look with sandals and sunglasses!
Fit & Features
- Textured mesh fabric, stretchy knit lining
- Dual spaghetti straps
- V-neckline
- High front slit
- Mermaid silhouette
- Runs true to size
Style Number/Barcode: 05102-5690
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Smooth Silhouette Ruched Bodycon Mini Dress
Sleek and smooth, this bodycon mini dress serves curves for days! Crafted from a soft double-lined knit fabric that fits like a glove, this dress features a square neckline adorned with adjustable spaghetti straps, side ruched seams to accentuate your figure along the bodycon silhouette, and a flattering mini-length hem. Complete the look with mules and a crop jacket.
Fit & Features
- Soft knit fabric lined with stretchy knit
- Adjustable spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5683
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oopsie Daisy Sleeveless A-Line Mini Dress
Oopsie daisy this sleeveless mini dress must've caught you by a sweet surprise! Crafted from a soft brushed knit fabric with an adorable floral print, this dress is a must-have for spring and summer. Features a flattering V-neckline with an adjustable drawstring tie and an A-line silhouette. Complete the look with a denim jacket and sandals for a casual occasion!
Fit & Features
- Floral print, brushed knit fabric lined with knit
- Adjustable drawstring neckline
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5686
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Alluring Vacay High Slit Tropical Mesh Midi Dress
Dare to allure on your next vacay in this sultry high slit tropical midi dress! The airy-lined mesh fabric is detailed with a bold all-over tropical palm leaf print to bring those dreamy destination vibes to your look. The mid-length dress features a sleeveless square neckline with pleating, spaghetti straps that lead to an open cross-back strappy design, a high-cut side slit to show off some leg, and a slim-fit silhouette to flaunt your figure. Style with hoop earrings and sandals for a beachy-chic outfit.
Fit & Features
- Tropical print
- Stretchy mesh fabric with knit lining
- Square neckline
- Spaghetti straps, open cross-back strappy design
- High side slit
- Slim-fit silhouette
- Runs true to size
Style Number/Barcode: 05102-5688
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Slay Halter Cowl Neck Ribbed Knit Maxi Dress
This sleek halter cowl neck maxi dress is a simple chic style that will make your casual outfits slay! Made with a lightweight stretchy ribbed knit fabric, it features a sleeveless draped cowl neckline with tie-back halter spaghetti straps, an alluring open back with a lower tie-back strap, and a form-hugging maxi-length silhouette to flaunt your stunning figure. Pair with slip-on sandals for a relaxing weekend getaway.
Fit & Features
- Stretchy ribbed knit fabric, partial front knit lining
- Cowl neckline, halter spaghetti straps
- Open back, tie-back strap
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5685
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Must-Have Tie Back A-Line Mini Dress
A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!
Fit & Features
- Slinky knit fabric lined with stretchy knit
- Open tie-back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5681
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Getaway Bound Tropical Print Woven Maxi Dress
Jet set to your gorgeous getaway in this tropical woven maxi dress! The lightweight gauze woven fabric features a bold tropical print to bring the allure to your dreamy vacay. The maxi-length dress is shaped with a strapless straight-across neckline with a ruffled fold-over design to add a flirty flair. The fitted high waist seam has an elasticized design for added stretch and a thin tie-front belt with cute tassel accents. The dress flows out to a floor-length hem with an effortless A-line silhouette. Style this maxi dress with strappy sandals.
Fit & Features
- Tropical printed gauze woven fabric with short knit lining, minimal stretch
- Strapless straight neckline with no-slip strip, ruffled fold-over design
- Fitted elasticized high waist seam
- Tie-front belt with tassels
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5678
Category Name: Casual Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Oh So Sweet Tie Back A-Line Mini Dress
You're going to look so sweet in this A-line mini dress for weekend plans! Featuring cap sleeves, a square neckline, and a tie-back design to turn heads. The A-line silhouette and mini-length hem will have you looking effortlessly chic! Complete the look in platform shoes.
Fit & Features
- Smooth knit fabric lined with stretchy knit
- Square neckline
- Tie back design
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5682
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In A Daze Strapless Cutout Striped Knit Mini Dress
The perfect striped mini dress for summer dazes and effortless styling! Crafted from a stretchy ribbed knit fabric with a trendy striped print, this dress features a strapless straight-across neckline and cutout design at the waist for an alluring vibe. The bodycon fit on the mini-length silhouette will accentuate your gorgeous curves. Style this dress with sunglasses and sandals!
Fit & Features
- Striped pattern
- Stretchy ribbed knit fabric
- Strapless straight neckline
- Waist cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 06005-1971
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Island Breeze Tropical Cutout Slit Maxi Dress
Feel the island breeze in this tropical maxi dress while on vacation! With a square neckline, spaghetti straps, and a form-hugging fit, this maxi dress is perfect for a day in the sun. The cutout bodice and high front slit add a touch of playfulness to your island look. Complete the look with sandals.
Fit & Features
- Tropical palm print, smooth stretchy knit fabric, sewn-in knit lining
- Square neckline
- Spaghetti straps
- Cutout bodice, high slit
- Form-hugging
- Runs true to size
Style Number/Barcode: 05102-5670
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Everyday Style Short Sleeve Ruched Mini Dress
Level up your everyday style with this simple yet chic mini dress! The lightweight smooth nylon fabric includes a knit lining and offers plenty of stretch for ultra-comfortable wear. Shaped with a classic scoop neckline and short sleeves, the mini-length dress features ruching down the side seams to flaunt your figure on the bodycon silhouette. Pair with a denim jacket and sneakers.
Fit & Features
- Smooth nylon fabric with knit lining, plenty of stretch
- Scoop neckline
- Short sleeves
- Ruched side seams
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5669
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Notice Me Abstract Print Bodycon Mini Dress
This abstract print dress will get you noticed at every party! Featuring adjustable spaghetti straps and a flattering square neckline, a mini-length hem, and a bodycon fit that hugs your natural curves. Complete the look with earrings and stiletto heels.
Fit & Features
- Abstract print, mesh fabric, sewn-in knit lining
- Square neckline
- Adjustable spaghetti straps
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5671
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Exceptional Bliss Lace-Up Floral Chiffon Maxi Dress
Answer that invite in exceptional blissful style in this floral chiffon maxi dress perfect for showers, graduations, or vacations! With spaghetti straps, a lace-up back, and a flowy ruffled silhouette, this maxi dress is both comfortable and stylish. The stretchy smocked waist and maxi floor-length hem provide a flattering look for any occasion. Complete the look with dainty earrings.
Fit & Features
- Floral print, chiffon fabric lined with woven fabric
- Spaghetti straps
- Lace-up back
- V-Neckline
- Flowy ruffled maxi silhouette
- Runs true to size
Style Number/Barcode: 05101-3345
Category Name: Casual Dresses
Price: $26.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Romance That Wows Large Blossom Floral Maxi Dress
Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!
Fit & Features
- Large blossoming floral print
- Mesh fabric lined with stretchy knit
- Spaghetti straps
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05101-3343
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Effortless Cutie Bow Lace-Up Floral Mini Dress
Look effortlessly cute in this floral mini dress this summer! The stretchy knit fabric is accented with a dainty floral print for a charming look. This bodycon dress features adjustable spaghetti straps and a sleeveless square neckline adorned with a ribbon bow and delicate crochet trim for a touch of elegance. The lace-up back allows for a perfect fit while the mini-length hem adds a flirty touch. Style with statement earrings.
Fit & Features
- Floral print, stretchy knit fabric
- Square neckline with ribbon bow and crochet trim
- Adjustable spaghetti straps
- Lace-up back
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5665
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Perfection Bodycon Striped Mini Dress
With this striped mini dress and sunnies, you'll be effortlessly cute for a perfect weekend out or vacation! Featuring a square neckline with a twist and spaghetti straps, this dress is designed to hug your body and accentuate your natural curves. The mini-length hem adds a flirty touch. Complete the look with sandals and sunnies!
Fit & Features
- Striped pattern, texture knit fabric, moderate stretch
- Spaghetti straps
- Square neckline with twist
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5675
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Charm Crew Neck Bodycon Midi Dress
The perfect basic midi dress for any occasion! It features a classic crew neck, cap sleeves, and a bodycon silhouette that flatters your curves. Pair with sleek heels and earrings.
Fit & Features
- Smooth jersey knit fabric, double-lined
- Crew neck
- Cap sleeves
- Bodycon silhouette
- Midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5661
Category Name: Casual Dresses
Price: $28.90
Availability: Out of Stock
Product Badge:- Sale
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Pleasant Cutie Collared V-Neck Belted Midi Dress
Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.
Fit & Features
- Woven fabric with lining, no stretch
- Collared V-neckline
- Button-down closures
- Adjustable belted waist with buckle
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3347
Category Name: Casual Dresses
Price: $9.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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What You Want Strappy Cutout Slit Midi Dress
This sleeveless midi dress is just what you want to elevate your everyday style! Featuring a flattering square neckline, spaghetti straps, and a strappy cutout twist back, this bodycon dress will make you stand out in any crowd. The side slit adds a touch of sexiness to the midi-length hem. Complete the look in sleek stiletto heels for upcoming weekend plans!
Fit & Features
- Double-lined rib knit fabric, moderate stretch
- Spaghetti straps
- Square neckline
- Strappy cutout twist back
- Side slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5663
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale