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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So Sweet Ruffled Cutout Skater Dress
Keep it so sweet with a charming ruffled skater dress! The dress features an off-the-shoulder neckline, a smocked bodice with a ruched drawstring, long sleeves, a sexy cutout at the midriff, and a tiered ruffled skater silhouette. The dress is composed of a lightweight gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.
Fit & Features
- Off-the-shoulder neckline
- Smocked bodice with a ruched drawstring
- Long sleeves, elastic cinched hems
- Cutout at the midriff
- Tiered ruffle skater skirt
- Gauze knit fabric, relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-2486
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Twirl Ruffled Skater Dress
Create a twirl-worthy moment with a floral dress that brings the romance! The dress features a sleeveless V-neckline, spaghetti straps, a strappy back, a ditsy floral print, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with no stretch. Complete look with wedges and a clutch.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Strappy back, back zipper and hook and eye closure
- Ditsy floral print
- Skater silhouette
- Lined gauze knit fabric, relaxed fit, no stretch
- Runs true to size
Style Number/Barcode: 05102-4101
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wrapped In Florals Chiffon Skater Dress
Wrap yourself in a fab floral dress this season for your next brunch! The dress features a floral print, plunging V-neckline, ruffled cap sleeves, an open back with a tie-back strap, and a skater silhouette with an asymmetrical ruffled trim. The dress is composed of a semi-sheer chiffon fabric that offers a form hugging fit with minimal stretch. Complete look with sandals and duster earrings.
Fit & Features
- Wrap V-neckline
- Ruffled cap sleeves
- Open back with tie back ties
- Skater silhouette
- Ruffle trim
- Floral print
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1103
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Own It Ribbed Knit Midi Dress
Own your look with a ribbed dress that makes a head-turning impression! The dress features a crew neckline, long sleeves, a sexy cutout at the waist, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a teddy jacket.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Cutout at the waist
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1079
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Finding Inspo Scoop Neck Mini Dress
Casual to dressy, this scoop neck mini dress is perfect for creating all sorts of stylish fits! Featuring long sleeves, a bodycon silhouette, and a slight low-back neckline on ribbed knit fabric. Complete the look in a trendy shacket and booties.
Fit & Features
- Long sleeves
- Scoop neck on front and back
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, double-lined
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4100
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babe For The Weekend Mini Dress
Be a bold babe in this classy stunner! This long sleeve mini dress features a wide scoop neckline on the front and back on a bodycon silhouette. Composed of a rib-knit fabric. Style with statement earrings for weekend soirees.
Fit & Features
- Long sleeves
- Wide scoop neck on the front and back
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4099
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic And Seamless Midi Sweater Dress
Chic and seamless, this sweater dress is perf for creating a simple yet elevated look. It features a sleeveless scoop neckline, adjustable spaghetti straps, a mid-length, curve-hugging silhouette, and a sultry thigh-high side slit. Style this dress with clear mules.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Mid-length, form-fitting silhouette
- High side slit
- Sweater knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-1085
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Charming Florals Chiffon Skater Dress
Charm them all with a floral dress that brings those sweet vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an open-back design with cute tie-back ties, and a skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges.
Fit & Features
- Floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Open back, tie-back ties
- Skater silhouette
- Chiffon fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1100
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Radiance Eyelet Mini Dress
Radiate in a gorge floral mini dress for your next brunch date! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of an eyelet knit fabric that offers a form hugging fit with minimal stretch. Complete look with mules and hoops.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini length silhouette
- Eyelet knit fabric
- Form hugging fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4091
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Chic Cut Out Mini Dress
Create a perf casual-chic look with this must-have mini dress. It features a sweetheart neckline, long fitted sleeves, an adjustable drawstring at the bust, a sultry waist cutout, ruching, and a short, form-hugging silhouette. Style this dress with sneakers.
Fit & Features
- Sweetheart neckline
- Long fitted sleeves
- Adjustable drawstring at the bust
- Waist cutout, ruching
- Mini-length, form-fitting silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4095
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Double Take Paisley Cutout Mini Dress
Make them take a double-take with a sexy mini dress that commands attention on your next GNO! The dress features a trendy paisley print, a halter neck, a twisted neck strap that allows you to customize the coverage of the bodice, cutout at the bodice, ruching, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Paisley print
- Halter neck
- Twisted neck strap, allows for adjustable coverage
- Cutout at the bodice
- Ruching
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4083
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pull In Closer Tie Dye Mini Dress
Pull in closer with a trendy mini dress! The dress features a tie-dye print, a crew neckline, long sleeves, ruched drawstrings, 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
- Tie-dye print
- Crew neckline
- Long sleeves
- Ruched drawstrings
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4084
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Style Icon Denim Mini Dress
Stun like the style icon you are with a mini dress that stuns! The dress features a sleeveless sweetheart neckline, lightly padded cups, adjustable spaghetti straps, corset-like seams at the bodice, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless sweetheart neckline
- Lightly padded cups
- Adjustable spaghetti straps
- Corset-like seams at bodice
- Mini length silhouette
- Denim fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4085
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Denim Dreams Lace-Up Mini Dress
Keep it dreamy with a denim mini dress that elevates your look! The dress features a sleeveless scoop neckline, spaghetti straps that lead to a lace-up back, vertical seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless scoop neckline
- Spaghetti straps
- Lace-up back, lower back zipper and hook and eye closure
- Vertical seams
- Mini-length silhouette
- Denim fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4089
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic High-Slit Basic Maxi Dress
Basic yet oh-so-chic, this sleeveless maxi dress will be your new go-to. It features a crew neckline, tank shoulder straps, a sultry thigh-high side slit, and a floor-length fitted silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Thigh-high side slit
- Floor-length fitted silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4090
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Hooked In Denim Mini Dress
Get hooked in with this cute mini dress that is part glam, part casual! The dress features a strapless sweetheart neckline, hook and eye front closures, corset seams, and a mini-length silhouette. The dress is composed of a denim fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Strapless sweetheart neckline
- Hook and eye front closures
- Corset seams
- Mini-length silhouette
- Denim knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4081
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Me In Glam Tie Dye Mini Dress
Keep it colorfully glam with a mini dress that is everything! The dress features a sleeveless square neckline, spaghetti straps, a tie-dye hue, a ruched body throughout, and a mini-length silhouette. Complete look with mules and statement cuff.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye hue
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4077
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Stunner Ribbed Knit Midi Dress
Stun on them with a stylish midi dress that makes a head-turning impression! The dress features a sleeveless V-neckline, spaghetti straps, an open back with an O-ring accent, and a midi-length silhouette. The dress is composed of a ribbed knit fabric that offers a form-hugging fit with a moderate stretch. Complete outfit with clear mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, O-ring accent
- Midi-length
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4071
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Style Cutout Maxi Dress
Showcase a stunning style this season in this trendy maxi dress. It features a sleeveless V-neckline, spaghetti straps, dual waist cutouts that lead to the back, and a floor-length, curve-hugging silhouette. Pair this sultry dress with hoop earrings and sleek heels.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Dual waist cutouts that lead to the back
- Floor-length, form-hugging fit
- Ribbed cotton fabric
- Runs true to size
Style Number/Barcode: 05102-4079
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Beauty Puff Sleeve Eyelet Skater Dress
Mesmerize with a skater dress that is perf for your next photoshoot! The dress features a square neckline, short puff sleeves, an eyelet pattern, and a skater silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Square neckline
- Short puff sleeves
- Eyelet pattern
- Skater silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4073
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Fab Tie Dye Ruched Mini Dress
Keep it totally fab with a ruched mini dress! The dress features a sleeveless square neckline, spaghetti straps, tie-dye print, a ruched body, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-dye print
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4078
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Darling Gingham Print Mini Dress
Stay on trend with a pretty mini dress that is perf for brunch with the squad! The dress features a sleeveless square neckline, spaghetti straps, gingham print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Gingham print
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4074
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropical Sunsets Maxi Dress
Your dream vacation is calling! Pack this stunning tropical floral printed maxi dress for a gorgeous look. It features an off-the-shoulder square neckline, a fitted smocked bodice, short ruffled sleeves, a tie-front accent to highlight the waist, and a flowy, floor-length silhouette with a wrap-front design. Style this dress with sleek hoop earrings and strappy sandals.
Fit & Features
- Off-the-shoulder square neckline
- Fitted smocked bodice
- Short ruffled sleeves
- Tie-front detail
- Flowy, floor-length silhouette, wrap-front design
- Woven fabric, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-4068
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Twist Long Sleeve Midi Dress
The twist back on this midi dress is pretty chic! It features long sleeves, a crew neckline, and a form-fitting silhouette. The dress is composed of a ribbed knit fabric with a moderate stretch. Perfect for styling with suede booties and a statement bracelet.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Twisted open back detail
- Midi-length hem
- Form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1075
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance