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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Check It Out Gingham Plaid Mini Dress
Make a statement in this gingham plaid mini dress! The square neckline and spaghetti straps make it the perfect dress for flaunting your curves, while the bodycon silhouette and mini-length hem radiate confidence. Complete the look by layering a long sleeve top for a preppy vibe!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Gingham plaid print
- Texture knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5243
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Caught In The Midi Crew Neck Tank Dress
A midi dress you wouldn't mind being spotted in! The dress features a sleeveless crew neck, a bodycon silhouette, and a fitted midi-length hem on stretchy rib knit fabric. Complete the look in a sleek layered necklace for lunch with friends!
Fit & Features
- Sleeveless crew neck
- Bodycon silhouette
- Fitted midi-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5242
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stunning Vision Abstract Mesh Midi Dress
You'll be a stunning vision in this mesh midi dress out for a day date or brunch! It features a sleeveless square neckline, adjustable spaghetti straps, side ruching that accentuates your natural curves, and a flattering bodycon silhouette. The dress is designed with an artsy abstract print on mesh fabric and has a sewn-in knit lining. Complete the look with a trendy denim crop jacket.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Side ruching, bodycon silhouette
- Midi-length hem
- Abstract print, mesh fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5496
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfectly Seasoned Plaid Crew Neck Mini Dress
Fabulous and flavor-filled, step into this plaid mini dress for the new season! The mini dress features fitted long sleeves, a classic crew neckline, and a flattering bodycon silhouette on stretchy knit fabric with a trendy plaid print. Complete the look in a moto jacket for a coffee shop hang!
Fit & Features
- Fitted long sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Plaid print
- Stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5247
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Element Turtleneck Long Sleeve Mini Dress
Soft and lightweight ribbed knit fabric crafts this trendy mini dress perfect for styling day to night! The mini-length dress features fitted long sleeves, a folded turtleneck, and a flattering bodycon silhouette on double-lined ribbed knit fabric. Complete the look in an oversized blazer and boots for brunch downtown or date night!
Fit & Features
- Double-lined ribbed knit fabric, moderate stretch
- Fitted long sleeves
- Folded turtleneck
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5245
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Muse Scoop Neck Mini Dress
A casual mini dress that's sure to become your fashion muse! The mini-length dress features fitted long sleeves, a scoop neckline, a built-in shelf bra for extra support, and a flattering bodycon silhouette on stretchy rib knit fabric. Complete the look in a moto jacket and boots for day or evening plans!
Fit & Features
- Fitted long sleeves
- Scoop neckline
- Built-in shelf bra
- Bodycon silhouette, mini-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5244
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Staple Tie-Front Ribbed Knit Midi Dress
This adorable tie-front midi dress is a stylish staple for an effortlessly chic look! It features a crew neckline, long fitted sleeves, a tie-front design at the waist, a mid-length hem with a high side slit, and a bodycon silhouette. The ribbed knit fabric offers plenty of stretch. Pair with ankle booties!
Fit & Features
- Stretchy ribbed knit fabric
- Crew neckline
- Long fitted sleeves
- Tie-front waist design
- High side slit
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5248
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stand Out Marble Print Cutout Midi Dress
Stand out this season and have all eyes on you in this marble print midi dress perfect for weekend getaways or sunset cocktails! The dress features a sleeveless square neck, spaghetti straps, a cutout bodice, and side ruched seams that accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker necklace.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cutout bodice
- Side ruched seams, bodycon silhouette
- Midi-length
- Marble print, smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5235
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Curve Allure Mock Neck Maxi Dress
Bring the allure to your look in this curve-flaunter maxi dress perfect for a dinner out with friends or date night! It features a sleeveless mock neck, bodycon silhouette, and side slit accent, and is crafted from smooth knit fabric with lining. Complete the look with a cute crop jacket.
Fit & Features
- Sleeveless mock neck
- Bodycon silhouette
- Side slit accent
- Maxi-length hem
- Smooth knit fabric, lined, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5232
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Check Me Out Plaid Bodycon Mini Dress
You'll be the object of everyone's gaze in this trendy plaid bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a stylish lower back cutout, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The stretchy brushed knit fabric features a chic windowpane plaid print. Complete your look with clear mules!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Lower back cutout
- Mini-length hem, bodycon silhouette
- Plaid print
- Brushed knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5230
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Throwback Blues Denim Print Mini Dress
Let this printed denim mini dress cure your throwback blues! It features a sleeveless square neckline, tank shoulder straps, a bodycon silhouette, and a mini-length hem on smooth and stretchy knit fabric. Complete the look with classic hoop earrings.
Fit & Features
- Sleeveless square neckline
- Tank shoulder straps
- Bodycon silhouette
- Mini-length hem
- Printed denim, smooth, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5229
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Curve-Hugging Chic Sheer Lace Maxi Dress
Flaunt your stunning silhouette in this casual curve-hugging sheer lace maxi dress. It features a crew neckline, short sleeves, dainty ruffled trims, a maxi-length hem with a back slit accent, and a bodycon fit. The sheer textured lace fabric offers a moderate stretch. Style with clear heels.
Fit & Features
- Crew neckline, short sleeves
- Back zipper and hook-eye closure
- Ruffled trims
- Maxi-length hem, back slit
- Bodycon silhouette
- Sheer textured lace fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5228
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer In Tie Dye Cutout Midi Dress
Spend your summer in this tie-dye midi dress perfect for backyard dinners to sunset cocktails! It features a sleeveless V-neckline, spaghetti straps, a sexy cutout waist, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in trendy doorknocker earrings.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Cutout waist
- Bodycon silhouette
- Midi-length hem
- Tie-dye print, stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5225
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Finders Keepers Tie Dye Mini Dress
Lucky you to have found this tie-dye mini dress! Perfect for summer fun, this sleeveless dress features a square neckline, spaghetti straps, adjustable side drawstrings let you customize the style, and a bodycon silhouette on stretchy rib knit fabric. Complete the look in strappy sandals for a backyard dinner party!
Fit & Features
- Sleeveless square neckline, spaghetti straps
- Adjustable side drawstrings
- Bodycon silhouette
- Mini-length hem
- Unique tie-dye print
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5224
Category Name: Casual Dresses
Price: $6.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Good Looks Mock Neck Long Sleeve Knit Midi Dress
This mock neck midi dress will look so good on you! The midi dress features fitted long sleeves, a flattering form-hugging fit, and a center back slit on soft and stretchy ribbed knit fabric. Complete the look with a moto jacket for day or evening plans!
Fit & Features
- Soft and stretchy ribbed knit fabric
- Mock neckline
- Fitted long sleeves
- Form-hugging fit
- Center back slit
- Runs true to size
Style Number/Barcode: 05102-5221
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic In The City Turtleneck Mini Dress
You'll look chic as you take a stroll in the city in this trendy turtleneck mini dress! It features a turtleneck that you can fold over, long fitted sleeves, ruching down the side seams, a mini-length hem, and a bodycon silhouette to showcase your curves. The soft brushed knit fabric offers plenty of stretch for comfortable wear. Style this mini dress with a faux leather blazer and over-the-knee boots for a cute fall 'fit.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Ruched side seams
- Mini-length hem
- Bodycon silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5220
Category Name: Casual Dresses
Price: $17.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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It's The Vibe Satin Cutout Maxi Dress
This maxi dress is the vibe for tonight! Going out has never looked so chic than on this sleeveless dress featuring a V-neckline, spaghetti straps, cutout sides and back, and a form-hugging silhouette with a flattering high side slit. Complete the look in lace-up stiletto heels.
Fit & Features
- Sleeveless V-neckline, spaghetti straps
- Cutout sides and back
- Form-hugging silhouette
- High side slit
- Maxi-length hem
- Smooth knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5218
Category Name: Casual Dresses
Price: $5.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vibrant Getaway Abstract Midi Dress
This abstract print midi dress was made for your next getaway! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, side ruched seams, and a flirty asymmetrical side slit along the hem. Complete the look in cute sandals.
Fit & Features
- Sleeveless square neck
- Spaghetti straps
- Bodycon silhouette, side ruched seams
- Asymmetrical side slit, midi-length hem
- Abstract print
- Smooth knit fabric, bust lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5216
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Iconic Basic Cap Sleeve Midi Dress
An iconic basic midi dress your closet needs! Create effortlessly chic looks with this knit dress featuring cap sleeves, a V-neck, and a bodycon silhouette with a curved hemline on brushed stretchy fabric. Style with slide sandals and sunglasses for hanging downtown with friends!
Fit & Features
- Cap sleeves
- V-neck
- Bodycon silhouette
- Curved midi-length hemline
- Brushed stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05101-2530
Category Name: Casual Dresses
Price: $5.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Invite Accepted Keyhole Slit Midi Dress
With this midi dress, you'll accept every invite just to show it off! Featuring a sleeveless scoop neckline, a spaghetti strap that cross in the back, a front keyhole bust cutout, a bodycon silhouette, and a flirty slit along the hem on smooth knit fabric. Complete the look in stiletto mules for a dinner date.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps, cross back
- Front keyhole bust cutout
- Bodycon silhouette
- Front slit, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5215
Category Name: Casual Dresses
Price: $5.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make It Sexy Off-The-Shoulder Mini Dress
Show off your curves in this sexy mini dress for weekend outings! The short dress features an off-the-shoulder neckline with a flirty bust keyhole tie, long sleeves with flared cuffs, side ruched seams to accentuate your figure, a bodycon silhouette, and a mini-length hem. Complete the look in lace-up stiletto heels and dare to be bold!
Fit & Features
- Off-the-shoulder neckline, bust keyhole tie
- Long sleeves with flared cuffs
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Slinky knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5212
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Most Noteworthy Ponte Pleated Mini Dress
A classic little black dress for your most noteworthy look for date night! The short dress features a sleeveless square neckline, spaghetti straps, and a side pleated seam that leads to the form-hugging mini-length hem on lined ponte fabric. Style the mini dress with a rhinestone necklace for a glam touch!
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side pleated seam
- Form-hugging silhouette
- MIni-length hem
- Lined ponte knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05103-5077
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The 'It' Knit Sleeveless Maxi Dress
Take your trendsetting status to chic summer style with this sleeveless knit maxi dress perfect for styling over your swimsuit! It features a scoop neckline, tank shoulder straps, a form-hugging fit, and a flirty high-side slit on crochet-style knit fabric with a short stretchy lining. Complete the look in sunglasses and sandals!
Fit & Features
- Sleeveless scoop neckline
- Tank shoulder straps
- Form-hugging fit
- High side slit
- Maxi-length hem
- Crochet-style knit fabric, short stretchy lining
- Runs true to size
Style Number/Barcode: 05102-5207
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Unique Feels Abstract Print Mock Neck Maxi Dress
Showcase your unique style in this artsy abstract print maxi dress for a gallery opening or a wine bar! It features cap sleeves, a mock neck, and a bodycon silhouette. The dress is composed of a sheer mesh fabric with a stretchy knit maxi slip lining with adjustable spaghetti straps, a scoop neck, and a fitted hem. Complete the look in platform sandals.
Fit & Features
- Cap sleeves
- Mock neck
- Bodycon silhouette, maxi-length hem
- Abstract print, mesh fabric
- Stretchy knit maxi slip lining, adjustable spaghetti straps
- Scoop neck, fitted hem
- Runs true to size
Style Number/Barcode: 05102-5208
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale