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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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
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Art Of Style Abstract Print Midi Dress
Show everyone how it's done! This sleeveless midi dress features a square neck, spaghetti straps, a side ruched seam that accentuates your curves along the bodycon silhouette, and a high side asymmetrical slit. The dress is designed with an artsy abstract print on smooth knit fabric. Complete the look with earrings for an art gallery opening!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Side ruched seam, bodycon silhouette
- High side asymmetrical slit
- Midi-length hem
- Abstract print, smooth knit fabric, moderate stretch
- Bust lining
- Runs true to size
Style Number/Barcode: 05102-5206
Category Name: Casual Dresses
Price: $5.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Charmed Mock Neck Bodycon Mini Dress
This bodycon mini dress would be charmed to make your acquaintance! A short dress that features fitted bell long sleeves and a mock neckline, and is composed of a rib knit fabric with a sewn-in knit lining. Style the mini dress with a chic crossbody bag for a day date!
Fit & Features
- Fitted bell long sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Rib knit fabric, sewn-in knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5204
Category Name: Casual Dresses
Price: $5.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Totally Iconic Bubble Mesh Bodycon Mini Dress
Create a fabulous club look that is totally iconic with this bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a mini-length hem, a bodycon silhouette that will flaunt your figure, and is composed of a textured bubble mesh fabric. The lined mesh fabric offers plenty of stretch. Style with platform heels.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini-length hem
- Bodycon fit
- Textured bubble mesh fabric, sewn-in knit lining
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5202
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flaunt Your Figure Bodycon Mini Dress
Flaunt your gorgeous figure in this curve-hugging mini dress! Featuring a sleeveless square neckline, bungee spaghetti straps, an alluring open back with a cross-back strap design, a mini-length hem, and a bodycon fit, you'll look amazing from any angle. The textured knit fabric offers plenty of stretch. Style with hoop earrings and clear heels.
Fit & Features
- Sleeveless square neckline, dart seam detailing
- Bungee spaghetti straps
- Open back, cross-back bungee strap design
- Mini-length hem
- Bodycon silhouette
- Textured knit fabric, smooth knit lining at the bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5205
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Style Icon Cutout Bodycon Midi Dress
This sultry-chic midi dress will level up your look and make you a casual style icon! It features a sleeveless asymmetric one-shoulder neckline with a tank strap, a bold asymmetric waist cutout for a hint of skin, a midi-length hem, and a bodycon silhouette that will hug your curves. The ribbed knit fabric offers plenty of stretch. Pair with clear mules.
Fit & Features
- Sleeveless asymmetric one-shoulder neckline
- Tank strap
- Asymmetric waist cutout
- Midi-length hem
- Bodycon silhouette
- Stretchy ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-5201
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Set The Curve Square Neck Maxi Dress
Set the tone for flaunting your curves in this essential maxi dress perfect for day or night styling! It features a sleeveless square neck, spaghetti straps, a bodycon silhouette, and a sexy center-back high slit on double-lined knit fabric with a buttery soft feel. Complete the look with a crop denim jacket and sandals for a sunset dinner date!
Fit & Features
- Sleeveless square neck, spaghetti straps
- Bodycon silhouette
- Center back high slit
- Maxi-length hem
- Double-lined knit fabric
- Buttery soft and stretchy
- Runs true to size
Style Number/Barcode: 05102-5200
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic And Simple Smooth Knit Mini Dress
This chic and simple smooth knit mini dress is the elevated basic you need! It features a sleeveless mock neckline, tank shoulder straps, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The buttery-soft and smooth double-lined knit fabric offers plenty of stretch. Style with hoop earrings and clear mules.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Mini-length hem
- Bodycon silhouette
- Soft and smooth double-lined knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5198
Category Name: Casual Dresses
Price: $5.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Real Showstopper Lace-Up Maxi Dress
A real showstopper of a maxi dress! Flaunt your best self in this sleeveless dress featuring a square neckline, spaghetti straps, an open lace-up back design, a ruched side seam, and a bodycon silhouette with a flattering high side asymmetrical slit on sleek knit fabric. Complete the look in block heels for a dinner date.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open lace-up back design
- Ruched side seam, bodycon silhouette
- High side asymmetrical slit, maxi-length fitted hem
- Sleek knit and stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-5346
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Plans Rib Knit Bodycon Maxi Dress
Casual plans? Look amazing in this sleeveless maxi dress for everything on your social calendar! It features a square neckline, spaghetti straps, a bodycon silhouette, and a fitted long hem on stretchy rib knit fabric. Complete the look in cute flower earrings and sandals.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Bodycon silhouette
- Maxi, fitted long-length hem
- Stretchy rib knit fabric
- Runs true to size
Style Number/Barcode: 05102-5195
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Chaser Cowl Neck Mini Dress
The perfect mesh mini dress for a sunset dinner by the beach! It features a sleeveless cowl neckline, sleek bungee spaghetti straps, and side-ruched seams to accentuate your curves along the bodycon silhouette. Complete the look with a sleek choker and earrings.
Fit & Features
- Sleeveless cowl neckline
- Bungee spaghetti straps
- Side ruched seams, bodycon silhouette
- Mini-length hem
- Sunset beach graphic design
- Mesh fabric, stretchy knit lining
- Runs true to size
Style Number/Barcode: 05102-5197
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Definite Yes High Slit Maxi Dress
This sleek high slit maxi dress is a definite yes for leveling up your casual looks! It features a sleeveless cowl neckline, spaghetti straps, a maxi-length hem with a thigh-high front slit to showcase some leg, and a slim-fit silhouette. The smooth knit fabric offers plenty of stretch. Style with strappy sandals for a lunch date!
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Maxi-length hem
- High front slit
- Slim-fit silhouette
- Smooth and stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5194
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale