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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All The Right Moves Ruched Mini Dress
Make all the right moves with a mini dress that showcases your curves! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched body
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4275
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Strappy Waist Sleeveless Midi Dress
This ribbed knit midi dress is the perf option for a casual yet still sultry look! It features a sleeveless crew neckline, tank shoulder straps, a front waist cutout with a strappy design, and a mid-length, curve-hugging silhouette with a chic side slit. Style this dress with strappy heels.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Front waist cutout, strappy design
- Mid-length, form-hugging fit
- Side slit
- Lined ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4272
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Retro Mood Tie Dye Midi Dress
Channel a retro mood with a midi dress that is totally fab! The dress features a tie-dye print, a crew neckline, short sleeves, and a high side slit with a twist knot accent. The dress is composed of smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a denim jacket.
Fit & Features
- Crew neckline
- Short sleeves
- High side slit, twist knot accent
- Tie-dye pattern
- Midi length silhouette
- Cotton kbit fabric
- Form-hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4271
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Making My Mark Ribbed Mini Dress
Make your style mark with a mini dress that is part casual, part glam! The dress features a sleeveless crew neckline, tank shoulder straps, and an open back with criss-cross straps. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Open back, criss-cross straps
- Lined ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4270
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Glam Button Down Mini Dress
Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Shoulder pads
- Mini length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4265
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wild At Heart Brushed Knit Leopard Mini Dress
Showcase your wild side in a mini dress that makes a fierce impression! The dress features a leopard print, a crew neckline, long sleeves, ruched drawstrings, and a mini-length silhouette with a rounded hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto and ankle booties.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched drawstrings
- Leopard print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4263
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Glam Button Down Mini Dress
Channel that effortless glam with a mini dress that stuns! The dress features a collared neckline, a button-down front, long sleeves, shoulder pads, and a mini-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Shoulder pads
- Mini length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4264
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Daring Button Up Midi Dress
Dare to button up in a midi dress that showcases your curves. The dress features a collared neckline, a button-down front, long sleeves, dual waist cutouts, and a midi-length silhouette. The dress is composed of a slinky lurex knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and sleek hoops.
Fit & Features
- Collared neckline
- Button-down front
- Long sleeves
- Dual waist cutouts
- Midi length silhouette
- Lurex-knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4268
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Trendy Collared Mini Dress
Keep your everyday fall look trendy and on point with this casual-chic mini dress! It features a collared V-neckline, long fitted sleeves with slit details at the hems, a vertical seam detail running down the center with ruching, and a short, curve-hugging silhouette. Style this dress with knee-high boots.
Fit & Features
- Collared V-neckline
- Long fitted sleeves, slit details at the hems
- Vertical seam detail down the center, ruching
- Mini-length, form-fitting silhouette
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4266
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruched Babe Long Sleeve Mini Dress
Flaunt your figure in this crowd-pleasing mini dress featuring side ruching with ties on a form-hugging silhouette. The smooth knit fabric offers a moderate stretch. Perfect for styling with heels and a clutch.
Fit & Features
- Crew neck
- Long sleeves
- Side ruching with ties
- Form-hugging silhouette
- Mini-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4259
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summertime Beauty Cutout Midi Dress
Hey beauty! Get a gorgeous look perf for summertime in this stunning midi dress. It features a sleeveless halter neckline, dual waist cutouts, and a mid-length, form-fitting silhouette to hug your curves. Style this dress with strappy sandals.
Fit & Features
- Sleeveless halter neckline
- Dual waist cutouts
- Mid-length, form-hugging fit
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-4255
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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The Minimal Satin High Slit Mini Dress
Keep it minimal and sleek with a mini dress that is perf to dress up for your next date night! The dress features a sleeveless V-neckline, adjustable spaghetti straps, and a mini side slit. The dress is composed of a satin fabric that offers a form hugging fit with minimal stretch. Complete look with rhinestone heels and statement earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Mini side slit
- Satin fabric, additional knit lining
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4254
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Day Dates Long Sleeve Button Down Dress
This bodycon mini dress is totally date-worthy! It features long sleeves, a collared neckline, button-down closure with ruching, and a bodycon silhouette. The dress is composed of a soft knit fabric with a moderate stretch. Complete the look with booties and statement jewelry.
Fit & Features
- Long sleeves, collared neckline
- Button-down with ruching
- Bodycon silhouette
- Short length hem
- Soft knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4262
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Raising The Bar Plaid Mini Dress
Raise the bar with a mini dress that is part classy, part casual! The dress features a plaid print, a sleeveless square neckline, and a mini-length silhouette. The dress is composed of a lined knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a denim jacket.
Fit & Features
- Plaid print
- Sleeveless square neckline
- Mini length silhouette
- Lined knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4256
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pretty In Plaid Mini Dress
Look and feel like a total babe wearing this plaid mini dress! It features a sleeveless, square neckline with spaghetti straps on a form-hugging fit offering a moderate stretch. Complete your daytime look with a cropped jacket.
Fit & Features
- Sleeveless, square neckline
- Spaghetti straps
- Plaid print
- Form-hugging fit
- Polyester fabric with moderate stretch
- Mini-length silhouette
- Runs true to size
Style Number/Barcode: 05102-4258
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute As A Button V-Neck Midi Dress
You're cute as can be in this v-neck midi dress perfect for a day date! It features long sleeves, a button-down front, midi length hem on a form-fitting silhouette. The rib-knit fabric offers a moderate stretch. Style with chic heels.
Fit & Features
- Long sleeves, v-neckline
- Button-down front
- Midi length hem
- Form-fitting silhouette
- Rib knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4257
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Thinking About Knit Cutout Midi Dress
You've got knit on the mind, show off in a midi dress that stuns! The dress features a crew neckline, short sleeves, a knot accent at the center with dual cutouts at the waist, and a midi-length silhouette that is accented with a high side slit. The dress is composed of a cotton knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and a clutch.
Fit & Features
- Crew neckline
- Short sleeves
- Twist knot accent
- Dual cutouts at the waist
- Midi-length silhouette, high side slit
- Cotton knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4261
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stay Cozy Cable Knit Mini Dress
Keep it cozy with a mini dress that is perf for a casual date night! The dress features a wrap V-neckline, long balloon sleeves with ribbed cuffs, a cinching tie waist with belt loops, and a mini-length silhouette. The dress is composed of cable knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties.
Fit & Features
- Wrap V-neckline
- Long balloon sleeves, ribbed cuffed hems
- Tie-waist belt with belt loops
- Mini-length silhouette
- Cable knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4250
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy And Cute Cable Knit Mini Dress
Get a cozy and cute look this season in this adorable cable knit mini dress! It features a wrap front and back design with a deep V-neckline, long loose sleeves with tapered hems, a tie-front waist, and a short, curve-hugging fit. Pair this dress with thigh-high boots for a date night.
Fit & Features
- Wrap front and back
- V-neckline
- Long sleeves
- Tie-front waist
- Mini-length silhouette, form-hugging fit
- Cable knit fabric with moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4251
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Denim Spirit Tie-Back Mini Dress
Cute, casual, with the spirit of denim in a sleek bodycon mini dress! Features a sleeveless, square neck, spaghetti straps, and a tie-back closure on a sultry open-back design. Complete the look in strappy mules for a day date.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Open tie-back, zipper closure
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4248
Category Name: Casual Dresses
Price: $4.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Girl Vibes Tie-Dye Mini Dress
Bring those effortless cool girl vibes in this fab tie-dye mini dress. It features a square neckline, short sleeves, and a short, curve-hugging silhouette. Style this knit dress with sneakers to keep it casual or clear heels for an elevated glam look.
Fit & Features
- Square neckline
- Short sleeves
- Mini-length, form-hugging fit
- Tie-dye print
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-4249
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feelin' Wild Sleeveless Slip Dress
Showcase a chic wild style in this sleeveless slip dress! It features a lined V-neckline, spaghetti straps, a cute tie-back detail, and a flirty short silhouette with a subtle flared-out hem. The lightweight woven fabric has a trendy all-over animal print. Complete the look with strappy mules.
Fit & Features
- Sleeveless lined V-neckline
- Spaghetti straps
- Tie-back detail
- Mini-length silhouette
- Woven fabric, no stretch, animal print
- Runs true to size
Style Number/Barcode: 05102-4245
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweetest Frame Long Sleeve Midi Dress
Bring the sweetness in this long sleeve midi dress featured in a sweetheart neck, bodycon silhouette, and midi-length hem. The dress is composed of a rib-knit fabric offering a moderate stretch. Complete the look with chic booties.
Fit & Features
- Long sleeves
- Sweetheart neckline
- Bodycon silhouette
- Midi-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1179
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strut And Snap Ribbed Knit Midi Dress
Strut it out in a knit midi dress that is perf for every day! Designed with a ribbed knit fabric, this dress offers a form-hugging fit with a moderate stretch. It features a sleeveless square neckline, tank shoulder straps, a high side slit accented with glossy metal buttons, and a midi-length hem. Complete the look with mules.
Shop More Sweater Dresses: Sweater Dress Collection
Fit & Features
- Ribbed knit fabric with moderate stretch
- Square neckline
- Tank shoulder straps
- Metal button accents
- Side slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1167
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free