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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She's All That Strapless Midi Dress
Feel confident in this stylish midi tube dress! The knee-length dress features a soft and comfortable textured knit fabric, combined with its strapless neckline and bodycon silhouette, making this the perfect look for any occasion. Style the midi dress with sleek heels for a birthday brunch.
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Midi-length hem
- Textured knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5311
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Change Of Season Long Sleeve Ribbed Knit Midi Dress
Step out this season in this casual-chic long sleeve midi dress! It features a V-neckline with a button design at the bust, long fitted sleeves, a midi-length hem with dual high-cut side slits, and a form-hugging fit. The lightweight ribbed knit fabric offers plenty of stretch for comfortable wear. Style this midi dress with a moto jacket and ankle booties for an edgy elevated look.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline, two-button design
- Long fitted sleeves
- Dual side slits
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-5310
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Another Day Long Sleeve Sweater Midi Dress
Another day, another slay in this sweater midi dress - perfect for pumpkin patches, grabbing a PSL, or meeting up with friends! The knee-length dress features fitted long sleeves, a crew neckline, a bodycon silhouette, and a flirty front slit on soft and stretchy rib knit fabric. Complete the look in booties and a chic crossbody bag.
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Front slit accent
- Midi-length hem
- Soft, stretchy sweater rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5305
Category Name: Casual Dresses
Price: $5.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Demeanor Mock Neck Ribbed Knit Midi Dress
Stay sweet and comfy in this ribbed knit midi dress perfect for any occasion! Designed with cap sleeves, a mock neckline, and a flattering bodycon silhouette, this mid-length dress is trend-worthy with a flirty front slit along the hem. Complete the look with a cute crop jacket and booties!
Fit & Features
- Stretchy ribbed knit fabric
- Mock neckline
- Cap sleeves
- Bodycon fit
- Front slit, midi-length hem
- Runs true to size
Style Number/Barcode: 05102-5304
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Out For A Ride Denim Moto Belted Mini Dress
This moto denim mini dress brings edgy perfection for your next ride downtown! It features a sleeveless lapel collar neckline, a front exposed zipper closure, a flattering bodycon silhouette, and a belted waist with belt loop accents and buckle closure. Complete the look in sleek hoop earrings.
Fit & Features
- Sleeveless lapel collar neckline
- Front exposed zipper closure
- Bodycon silhouette
- Belted waist, belt loop accents, buckle closure
- Mini-length hem
- Denim fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5307
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Caught On-Trend Basic V-Neck Midi Dress
Get caught on trend always in this basic midi dress for casual slays! It features cap sleeves, a V-neckline, a flattering bodycon silhouette, and a midi-length hem on soft modal knit fabric with a stretchy mesh lining. Complete the look with a ring set and heels.
Fit & Features
- Cap sleeves
- V-neckline
- Bodycon silhouette
- Midi-length hem
- Soft modal knit fabric, stretchy mesh lining
- Runs true to size
Style Number/Barcode: 05102-5306
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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See Through Me X-Ray Graphic Maxi Dress
See through the ordinary and showcase your unique style! This graphic maxi dress features a scoop neckline, adjustable spaghetti straps, an X-ray graphic bust and front design, a flattering bodycon silhouette, and a back slit on smooth knit fabric. Complete the look in a sassy crop denim jacket for day or night plans!
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps,
- Back zipper and hook-eye closure
- X-ray graphic bust and front design
- Bodycon silhouette, maxi-length hem, back slit
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5297
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Artistic Muse Abstract Strapless Midi Dress
You'll be the artsy muse in this abstract print mesh midi dress for gallery openings or an evening downtown! It features a strapless cowl neckline, flattering side ruched seams that accentuate your curves, a bodycon silhouette, and a side slit accent. Complete the look in clear strap heels for a seamless style!
Fit & Features
- Strapless cowl neckline
- Back zipper and hook-eye closure
- Side ruched seams, side slit
- Bodycon silhouette, midi-length hem
- Abstract print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5295
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Extra Flare V-Neck Skater Dress
Give your look extra flare in this sweet sleeveless skater dress! It features a V-neckline, tank shoulder straps, and a flattering fit and flare short-length silhouette. The dress is composed of a smooth knit fabric with plenty of stretch. Complete the look in rhinestone stiletto heels for a birthday or a dressy date night!
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Skater silhouette
- Short-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5292
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Abstract Moment Mesh Mock Neck Midi Dress
Step out in this stylish mesh midi dress and not miss a single moment to have all eyes on you! The knee-length dress features a feminine mock neck with back button closures, fitted sheer long sleeves, and bodycon silhouette with abstract print on mesh fabric. Complete the look with gold hoop earrings for an art gallery opening and dinner downtown!
Fit & Features
- Mock neck, back button closures
- Fitted sheer long sleeves
- Bodycon silhouette
- Midi-length hem
- Abstract print
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5294
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Cute Sleeveless Ruched Slit Midi Dress
For casual plans and outings, make your look cute in this sleeveless midi dress perfect for inspiring your inner fashionista! It features a square neck, spaghetti straps, a form-hugging fit, a side ruched seam that accentuates your curves, a side slit, and a midi-length hem. Complete the look with a crop jacket and heels!
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Form-hugging fit
- Side ruched seam, slit
- Midi-length hem
- Stretchy brushed knit soft fabric
- Runs true to size
Style Number/Barcode: 05102-5290
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy New Vibe One-Shoulder Skater Dress
This adorable sleeveless skater dress will give off a trendy new vibe that will get all the compliments. It features an asymmetric one-shoulder neckline, dual adjustable spaghetti straps that continue to an asymmetric back strappy design, dual vertical seams down the front, a short-length hem, and a flared-out skater silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Style with clear mules!
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Dual adjustable spaghetti straps
- Asymmetric back strappy design
- Dual vertical seams down the front
- Short-length hem, skater silhouette
- Smooth knit fabric, full-length lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5291
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Flirt Sleeveless A-Line Short Dress
Breeze in looking casual and flirty in this short dress at parties and date nights! It features a sleeveless square neck, spaghetti straps, and a flattering A-line silhouette on smooth knit fabric. Complete the look in a necklace and earrings set.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- A-line silhouette
- Short-length hem
- Smooth knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5287
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casually Effortless Smooth Knit Bodycon Mini Dress
Enjoy an effortless day or night out with this casual smooth knit mini dress! Its strapless neckline and bodycon silhouette are perfect for showing off those curves, while the mini-length hem ensures you get noticed! The dress is composed of a slinky smooth knit fabric with a stretchy knit lining. Complete the look in sassy lace-up sandals.
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Mini-length hem
- Slinky smooth knit fabric, stretchy knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5289
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Allure Sleeveless A-Line Short Dress
Showcase a classic allure in this chic sleeveless A-line short dress. It features a high mock neckline with tie-back straps, an open-back design, a fitted high waist seam, a short-length hem, and a flowy A-line silhouette. The buttery-smooth knit fabric includes a full lining and has plenty of stretch. Complete your look for happy hour with sleek pumps.
Fit & Features
- Sleeveless high mock neckline, tie-back straps
- Open back
- Fitted high waist seam
- Short-length hem
- A-line silhouette
- Smooth knit fabric, full-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5288
Category Name: Casual Dresses
Price: $5.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's The Main Rib Knit Strapless Midi Dress
Flaunt your look with ease and chicness with this midi dress this season! The knee-length dress features a strapless neckline, a flattering bodycon silhouette, and a fitted maxi-length hem on soft and stretchy rib knit fabric with a short knit lining. Style with the matching bolero and heels for weekend plans!
Shop Matching Bolero: She's The Main Rib Knit Slouchy Bolero
Fit & Features
- Strapless neckline
- Bodycon silhouette
- Fitted midi-length hem
- Soft and stretchy
- Rib knit fabric, short knit lining
- Runs true to size
Style Number/Barcode: 05102-5872
Category Name: Casual Dresses
Price: $19.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Playful Prints Satin Pleated Skater Dress
Play up your colorful side in this satin skater dress perfect for summer! It features a sleeveless V-neckline, adjustable spaghetti straps, a ruched tie-front bust, a stretchy smocked back, a flirty cutout, and a pleated short-length hem. The dress is designed with a multi-colored geometric print on smooth woven satin fabric. Complete the look in lace-up heels.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Ruched tie-front bust, stretchy smocked back
- Cutout accent, skater silhouette
- Pleated short-length hem
- Multi-colored geometric print
- Smooth woven satin fabric, no stretch, bust lining
- Runs true to size
Style Number/Barcode: 05102-5284
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On The Down Low Denim Strapless Midi Dress
Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!
Fit & Features
- Strapless neckline
- Stretchy smocked back
- Button-down front closures
- Bodycon silhouette, midi-length hem
- Belt loop accents, three-pocket styling
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5283
Category Name: Casual Dresses
Price: $5.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Loved In Lace V-Neck Long Sleeve Short Dress
A divine lace short dress for modern brides, birthday babes, or any dressy occasion! The mini dress features sheer lace long sleeves with flared cuffs, a V-neckline, a bodycon silhouette that hugs your curves and is composed of a lace knit fabric with stretchy knit lining. Complete the look with fringe earrings and heels.
Fit & Features
- Sheer long sleeves, flared cuffs
- V-neckline
- Bodycon silhouette
- Short-length hem
- Lace knit fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05101-3171
Category Name: Casual Dresses
Price: $20.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curves For Days Off-The-Shoulder Midi Dress
Serve major curves in this off-the-shoulder midi dress at parties and dressy occasions! Featuring a flattering off-the-shoulder sweetheart neckline and a tie-front bust, this dress accentuates your figure in all the right ways. The cutout bodice adds a flirty charm, while the ruched seams and bodycon fit hug your figure for a sultry silhouette on mesh-lined fabric. Complete the look in stiletto heels.
Fit & Features
- Mesh fabric lined with stretchy knit
- Back zipper and hook-eye closure
- Tie-front bust, cutout bodice
- Side ruched seams
- Center back slit
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05101-2623
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fashion Zilla Mock Neck Texture Mini Dress
A fashionista like you will go crazy for this iconic mini dress! It features a mock neckline, cap sleeves, and a flattering bodycon silhouette on stylish textured mesh fabric with a stretchy knit lining. Complete the look in sleek sunglasses and booties for an edgy-fab vibe!
Fit & Features
- Mock neckline
- Cap sleeves
- Bodycon silhouette
- Mini-length hem
- Textured mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5278
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Colorful Sensation Abstract Print Maxi Dress
Be the colorful sensation in whatever room you walk into wearing this abstract print midi dress! It features a sleeveless square neckline, spaghetti straps, a bodycon silhouette, and an adjustable ruched drawstring atop a sultry slit. Complete the look with a chic handbag for an art gallery opening or sunset cocktails!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Adjustable ruched drawstring, high slit
- Maxi-length hem
- Abstract print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5279
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Off My Mind Cutout Long Sleeve Ribbed Knit Midi Dress
Make an unforgettable appearance in this long-sleeved midi dress at brunch or casual parties! The midi dress is designed with an off-the-shoulder neckline, a twisted bust with a sultry cutout, and a bodycon fit on stretchy ribbed knit fabric. Complete the look in strappy heels.
Fit & Features
- Ribbed knit fabric with moderate stretch
- Off-the-shoulder neckline
- Fitted long sleeves
- Twisted bust, cutout
- Bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5280
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Dreaming In Marble Asymmetrical Midi Dress
Finished with a gorgeous marble print, this midi dress will be the star of the night! The knee-length dress features a sleeveless V-neckline, adjustable spaghetti straps, a crisscross back, and a bodycon silhouette and side ruched seam that flatters your curves, while the asymmetrical midi-length hem and high side slit show off your legs. Style the midi dress with basic stiletto heels for a sunset dinner.
Fit & Features
- Sleeveless V-neckline, adjustable spaghetti straps
- Crisscross back
- Bodycon silhouette
- Side ruched seam, high side slit
- Asymmetrical midi-length hem
- Marble print, bust knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5274
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale