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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Sweetie Status Halter Crochet Trim Babydoll Dress
You'll look absolutely adorable in this babydoll dress at showers, birthdays, or backyard parties! The halter neckline and cutout bodice add a touch of allure, while the crochet trim and babydoll silhouette create a delicate and feminine look along the short-length hem. Complete the look in sandals and hoop earrings.
Fit & Features
- Gauze woven fabric, woven lining, no stretch
- Halter neckline with spaghetti strap ties
- Cutout bodice
- Crochet trim
- Babydoll silhouette
- Runs true to size
Style Number/Barcode: 05102-5421
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunny Days Square Neck Tie-Back Skater Short Dress
Sunny days pair perfectly with this skater short dress for casual occasions or day dates! Made from lightweight cotton, this dress boasts a square neckline and elasticized cap sleeves for a perfectly feminine touch. The smocked bodice and tie-back waist ensure a flattering fit, while the tiered skater silhouette adds a playful flair. Complete the look with sandals, sunglasses, and a purse for a cute style!
Fit & Features
- Lightweight cotton fabric with woven lining
- Stretchy smocked bodice
- Tie-back waist
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5417
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Beyond Precious V-Neck Ruffle Babydoll Dress
You'll be looking beyond precious in this babydoll dress - the perfect summer staple! The ruffle trim shoulder straps and v-neckline create a delicate and alluring look, while the ruffled babydoll silhouette and side pockets add a touch of playful charm to the short-length hem. Complete the look in trendy sandals.
Fit & Features
- Woven fabric, bust lining, no stretch
- Ruffle trim shoulder straps
- V-neckline
- Ruffle babydoll silhouette
- Side pockets
- Runs true to size
Style Number/Barcode: 05102-5422
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Spice Things Up V-Neck Cutout Skater Dress
Casual gets a sultry upgrade with this short skater dress perfect for showers and birthdays! This flirty skater dress boasts flowy sleeves, a front and back V-neckline, and a cutout bodice for an alluring look. The gauze fabric adds breezy comfort while the skater silhouette and short length keep you on-trend. Complete the look in strappy wedges.
Fit & Features
- Gauze woven fabric lined with stretchy knit
- V-Neckline front and back
- Cutout bodice, elasticized straps
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05102-5419
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sunny Scoop Neck Skater Eyelet Mini Dress
Sunshine days are ahead and this skater mini dress is perfect for enjoying the weekend and weather! Crafted from an adorable eyelet knit fabric, this mini dress is designed with a flattering scoop neckline, adjustable spaghetti straps for a perfect fit, and a flirty tie-back detail to show off your style. The skater silhouette and tiered ruffled hem allow for movement and a fashionable sway with every step! Complete the look in heeled sandals.
Fit & Features
- Eyelet knit fabric, sewn-in knit lining
- Adjustable spaghetti straps
- Tie-back detail
- Skater silhouette
- Tiered ruffles
- Runs true to size
Style Number/Barcode: 05102-5426
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make A Debut Plaid Strapless Pleated Mini Dress
Make a debut in classic plaid and on-trend silhouette! This plaid mini dress is sure to stand out from any crowd. Featuring a strapless neckline, form-hugging bodice, belt loop accents, and a flirty pleated mini-length hem. Complete the look in lug boots for an edgy vibe!
Fit & Features
- Strapless neckline
- Back zipper closure
- Form-hugging bodice
- Belt loop accents
- Pleated mini-length hem
- Plaid print, woven fabric, knit lining at the bust, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5415
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cherry On Top Lace-Up Cutout Chiffon Skater Dress
Nothing says wow like this chiffon skater dress that puts the cherry on top of your look at brunch, birthdays, or shower celebrations! Designed with a V-neckline, adjustable ruffled straps, and a pleated bust, this dress accentuates your curves. The cutout waist and back with lace-up detailing add a playful touch, while the skater silhouette and tiered ruffled hem give a flirty and flattering fit! Complete the look in fashionable platform sneakers.
Fit & Features
- Chiffon fabric lined with woven fabric
- Adjustable ruffled straps
- Lace-up, back zipper hook-eye closure
- Cut out sides and back
- Ruffled
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2947
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.
Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ready For Romance Floral Velvet Lace Mini Dress
Unleash your inner daring in this floral velvet mini dress on an evening out! With a lace-trim V-neckline, sleek adjustable bungee spaghetti straps, and a low-cut back, this bodycon dress will turn heads. The front bow adds a touch of romance, while the floral velvet pattern on mesh fabric adds an alluring texture. Complete the look with a clutch, heels, and a bolero for a stylish head-to-toe outfit!
Fit & Features
- Floral velvet pattern, mesh fabric lined with knit
- Bungee adjustable spaghetti straps
- Lace trim and bow inset
- Back zipper and hook-eye closure
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05103-5315
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Girl Energy Houndstooth Knit Mini Dress
Bring the chic girl energy to your fall wardrobe with this trendy mini dress! It features a sleeveless square neckline, spaghetti straps, a mini-length hem, and a bodycon silhouette to showcase your curves. The knit fabric features an all-over houndstooth pattern for an elevated vibe. Style this mini dress with a faux leather moto jacket and combat boots!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length hem
- Bodycon silhouette
- Houndstooth pattern
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5410
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Stylish And Classic Plaid Mini Dress
This stylish mini dress features a classic plaid print and a bodycon silhouette in soft knit fabric. Its square neckline, spaghetti straps, and mini-length hem make it perfect for a trendy, dressy look for layering. Style with a chic moto jacket and boots for an evening out!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Plaid print, knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5411
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Zip It Long Sleeve Cargo Pocket Mini Dress
This casual mini dress is perfect for the fashionista with an eye for style! Its fitted long sleeves, crew neckline, and zipper closure give a classic feel, while the bodycon silhouette, side cargo flap pockets, and mini-length hem on lined rib knit fabric create a flattering and unique style. Complete the look with booties for day or night plans!
Fit & Features
- Fitted long sleeves, crew neckline
- Front zipper closure
- Bodycon silhouette
- Side cargo flap pockets
- Mini-length hem
- Lined stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5407
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shine All Way Metallic Woven Skater Dress
Shine all way to and from the party in this breezy skater dress! It features a sleeveless V-neck, adjustable spaghetti straps, a stretchy smocked waist, and a flattering skater silhouette with a ruffled short-length hem. The dress is crafted from an airy woven fabric with shimmering metallic threads and has a stretchy knit lining. Complete the look in stiletto heels.
Fit & Features
- Sleeveless V-neck
- Adjustable spaghetti straps
- Stretchy smocked waist
- Skater silhouette
- Ruffled short-length hem
- Metallic threads, airy woven fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5405
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Lineup Mock Neck High Slit Midi Dress
This alluring mock neck high slit midi dress needs to be in your winter lineup! It features a mock neckline, long fitted sleeves, a trendy ruched side seam with an adjustable drawstring, an asymmetric midi-length hem creating a high-cut side slit, and a form-hugging silhouette to flaunt your figure. The brushed knit fabric offers plenty of stretch. Style this midi dress with ankle booties!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Ruched side seam, adjustable drawstring
- Asymmetric midi-length hem, high-cut side slit
- Form-hugging silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5404
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Attract And Allure Marble Print Midi Dress
Attract and allure in this marble print midi dress that puts your curves on display! It features a high crew neckline, long fitted sleeves, a midi-length hem with a form-hugging silhouette, and an all-over trendy marble print pattern. The sheer mesh fabric includes a full-length sleeveless knit lining. Style this mid-length dress with clear heel mules for a cool-girl vibe for a rooftop bar!
Fit & Features
- Crew neckline
- Long fitted sleeves
- Midi-length hem, form-hugging fit
- Marble print, sheer mesh fabric
- Full-length sleeveless knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5403
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Season Of Fun Denim Collared A-Line Mini Dress
It's the season of fun with this casual and cute denim mini dress perfect for everyday styling! It features long sleeves with dual button cuffs, a collared neckline, button-down front closures, two flap pockets, a belted waist with buckle closure, and a flattering A-line silhouette. Complete the look in sleek hoop earrings.
Fit & Features
- Long sleeves, dual button cuffs
- Collared neckline
- Button-down front closures, two flap pockets
- Belted waist, buckle closure, belt loop accents
- A-line silhouette, mini-length hem
- Denim fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5402
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Right Impression V-Neck Floral Ruffle Skater Dress
A cutie like you will always make the right impression in this floral skater dress on dates or at brunch! Featuring sheer peasant long sleeves and a flattering V-neckline, this skater silhouette is completed with a ruffled short-length hem. The V-cut back with a spaghetti strap tie adds a touch of allure. Style this floral skater dress with block heels.
Fit & Features
- Floral print, chiffon fabric with woven lining, no stretch
- V-neckline, V-cut back with spaghetti strap tie
- Skater silhouette
- Ruffled short-length hem
- Runs true to size
Style Number/Barcode: 05101-2894
Category Name: Casual Dresses
Price: $6.97 $56.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In The Cut One Shoulder Cutout Mini Dress
Let your style speak volumes with this mini dress perfect for dates or birthday brunch! The mini-length dress features a one-shoulder neckline with a puff short sleeve, a side drawstring cutout, and a flattering form-hugging silhouette on texture woven fabric. Complete the look with an envelope clutch and heels.
Fit & Features
- One-shoulder neckline, puff short sleeves
- Side drawstring cutout
- Form-hugging silhouette
- Mini-length hem
- Texture woven fabric, slight stretch
- Runs true to size
Style Number/Barcode: 05102-5401
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cadet Babe Cargo Pocket Mini Dress
Take rank as a cadet babe in this sleeveless mini dress perfect for elevating your basics! It features a square neckline, spaghetti straps, cargo flap pockets with pull tabs, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look with a denim jacket.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cargo flap pockets, pull tabs
- Bodycon silhouette
- Mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5399
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Favorite Tune Sleeveless Tank Midi Dress
Get ready to sing about this sleeveless midi dress and how much you love it! With a stylish sleeveless square neckline and flattering shoulder straps, this midi dress will hug your curves in the form-hugging silhouette and show some skin with the front slit. Perfect for any occasion, style this midi dress with a denim jacket and long necklace for an effortlessly chic look!
Fit & Features
- Sleeveless square neckline, shoulder straps
- Form-hugging silhouette
- Front slit
- Midi-length hem
- Rib knit fabric, bust knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5397
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Can't Help It Off-The-Shoulder Sweater Dress
If chic comes naturally, this sweater maxi dress can't help but make your style shine! The maxi dress features an off-the-shoulder folded neckline, fitted long sleeves, a flattering bodycon silhouette, and a side slit on stretchy rib knit fabric. Complete the look in sleek stiletto heels for date nights or holiday parties!
Fit & Features
- Off-the-shoulder folded neckline
- Fitted long sleeves
- Bodycon silhouette, side slit
- Maxi-length hem
- Stretchy rib knit sweater fabric
- Runs true to size
Style Number/Barcode: 06005-1793
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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High Class Mock Neck Long Sleeve Midi Dress
Enjoy feeling like a boss in this high-class midi dress! The fitted long sleeves with thumbholes offer protection without compromising style, while the mock neckline, bodycon silhouette, and midi-length hem create a sleek and modern look. The stretchy ribbed knit fabric has a full-length lining. Complete the look with statement booties for a dinner downtown!
Fit & Features
- Fitted long sleeves with thumbholes
- Mock neckline
- Bodycon silhouette
- Midi-length hem
- Stretchy ribbed knit fabric, full-length knit lining
- Runs true to size
Style Number/Barcode: 05102-5396
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Out And About Long Sleeve Short Dress
This adorable long sleeve short dress is ideal for those casual days where you're out and about! It features a square neckline with a ruched bust and an adjustable tie-front drawstring, long fitted sleeves, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The lined brushed crepe fabric offers plenty of stretch. Style this short-length dress with a chunky knit cardigan and over-the-knee boots for a coffee date!
Fit & Features
- Square neckline
- Ruched bust, tie-front drawstring
- Long fitted sleeves
- High waist seam
- Short-length hem, A-line silhouette
- Brushed crepe fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5395
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Signature Style Collared Wrap Mini Dress
This wrap mini dress is perf for showcasing that signature chic style! It features a collared V-neckline with a pleated surplice design, long fitted sleeves, a high waist seam with ruched detailing to highlight your silhouette, a faux wrap-front design leading to an asymmetric mini-length hem, and a form-hugging fit. The knit fabric offers plenty of stretch. Complete your look with knee-high boots.
Fit & Features
- Collared V-neckline, pleated surplice design
- Long fitted sleeves
- High waist seam, ruching
- Faux wrap-front design, asymmetric mini-length hem
- Form-hugging fit
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-2948
Category Name: Casual Dresses
Price: $5.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale