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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Cute Weekend Vibes Ribbed Knit Mini Dress
This cute and cozy ribbed knit mini dress is perf for your weekend plans! It features a crew neckline, long fitted sleeves, ruched detailing down the side seams, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch. Style with knee-high boots to grab coffee with your friends.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Ruching down the sides
- Mini-length hem, fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4839
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sultry Style Strappy Back Midi Dress
Simple yet so alluring, you'll love the sultry style of this strappy back midi dress. It features a sleeveless V-neckline, spaghetti straps that lead to an open back with cross-back lace-up straps, a midi-length hem, and a bodycon silhouette that will hug your natural curves. The ribbed knit fabric offers plenty of stretch. Complete your look with clear heels and a chic handbag.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Open back, cross-back lace-up straps, tie closure
- Midi-length hem
- Bodycon silhouette
- Ribbed knit fabric, full knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4835
Category Name: Casual Dresses
Price: $5.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Color Me Pretty Ombre Midi Dress
Give your closet some pretty color with this ombre knit midi dress perfect for dressing up! The dress features a sleeveless scoop neck, sleek spaghetti straps, an open lace-up back with tie closure, a bodycon silhouette, and an asymmetrical side slit cutout to showcase some chic strappy heels.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Open lace-up back, tie closure
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Ombre lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4825
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Back Of My Mind Crepe Slip Dress
You'll be unforgettable once they see you in this crepe slip dress perfect for casual parties and celebrations! It features a sleeveless V-neck, spaghetti straps, a form-hugging silhouette, and a sultry front slit along the midi-length hem. Style with simple hoop earrings to complete the look!
Fit & Features
- Sleeveless V-neck, spaghetti straps
- Form-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4826
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take A Trip Sweater Halter Dress
Taking a trip somewhere fab? You're gonna need this sweater halter dress perfect for looking chic on the go! It features a sleeveless bodice, cross straps with neck-tie closure, a bodycon silhouette, and a mini-length hem. Complete the look in linear earrings.
Shop More Styles: The Sweater Collection
Fit & Features
- Sleeveless halter neck
- Cross straps, neck-tie closure
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1605
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Abstract Idea Mesh Printed Dress
Wear your art! This abstract mesh mini dress features a sleeveless square neck, adjustable spaghetti straps, front cutouts with rhinestone button accents, side ruched seams, and a bodycon silhouette. Complete the look in glitzy heels and earrings.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Front cutouts with rhinestone button accents
- Side ruched seams
- Bodycon, mini-length hem
- Abstract print, lined-mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4824
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Swirl Mesh Midi Dress
Captivate the room with your unique style! Unveil this swirl print midi dress featuring a sleeveless V-neckline with sleek spaghetti straps, a bodycon silhouette, and an asymmetrical hem with a side slit cutout. Complete the look in strappy heels for a birthday party.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Bodycon silhouette
- Asymmetrical midi hem, side slit cutout
- Swirl print
- Sheer mesh fabric, full knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4823
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wrap It Up Cable Knit Sweater Dress
Wrap yourself up in style this season! Cue compliments whenever you're in this cable knit sweater midi dress featuring long balloon sleeves, a v-neckline, and a surplice bodice with a tie-front waist belt and a bodycon silhouette. Style with pointed-toe booties to complete the look!
Fit & Features
- Long balloon sleeves
- V-neckline
- Surplice bodice
- Tie-front waist belt
- Bodycon silhouette
- Midi-length hem
- Cable knit fabric, minimal stretch
- Fits true to size
Style Number/Barcode: 05102-4818
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wear Your Art Striped Midi Dress
Wear this fine work of art and every eye will be on you! This marble striped midi dress features long sleeves, front and back v-necklines, a bodycon silhouette, and a tie-front waist. Complete the look in PVC mules for a casual lunch!
Fit & Features
- Long sleeves
- Front and back v-necklines
- Bodycon silhouette
- Tie-front waist
- Midi-length hem
- Marble striped print, stretch-knit fabric
- Fits true to size
Style Number/Barcode: 05102-4821
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Marvelous Mod Mesh Short Dress
So marvelously mod, this marble print mesh dress has entered the chat. It features a sleeveless square neckline, spaghetti straps, and side ruched seams to accentuate your curves along the bodycon silhouette. Complete the look in chunky platform heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Mini-length hem
- Marble print, mesh-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4819
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shape Of Me Backless Mini Dress
You'll fall in love with the shape of your curves in this body-hugging mini dress perfect for bachelorettes or going wine-tasting! It features a sleeveless V-neck, bungee spaghetti straps, and a backless design with a lower ruched seam to accentuate your assets on the bodycon silhouette. Complete the look in platform wedges.
Fit & Features
- Sleeveless V-neck
- Bungee spaghetti straps
- Backless design, lower ruched seams
- Bodycon silhouette
- Mini-length hem
- Brushed double-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-5026
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Of-The-Moment Chic Swirl Print Midi Dress
This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Hip-hugging fit, midi-length A-line silhouette
- Thigh-high front slit
- Swirl print pattern
- Jersey knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4817
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Cozy Turtleneck Mini Dress
You'll forever be cozy in this soft and stretchy brushed knit mini dress! It features a turtleneck, long fitted sleeves, and a short, curve-hugging, bodycon silhouette. Style with a plaid blanket scarf and knee-high boots.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Double-lined brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4811
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced Up For The Night Mini Dress
Heat up the night in this bombshell sleeveless mini dress featuring v-neckline, tank-style straps, a bodycon silhouette, and a cutout side with lace-up straps. Perfect for styling with strappy stiletto heels.
Fit & Features
- Sleeveless v-neckline
- Tank-style straps
- Bodycon silhouette
- Cutout side with lace-up straps
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4814
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cream Of The Crop Cutout Mini Dress
Look and feel your absolute best in this prize-worthy casual mini dress! It features a sleeveless, one-shoulder neckline with a thin shoulder strap, a sultry cutout waist with a hoop insert, and a bodycon silhouette. Complete the look in clear strap heels for a lunch date.
Fit & Features
- Sleeveless, one-shoulder neckline
- Thin shoulder strap
- Cutout waist, hoop insert
- Bodycon silhouette
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4806
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knot Pleasure Crew Neck Midi Dress
This crew neck midi dress will be pleased to be added to your fashion closet! It features long fitted sleeves, a form-hugging silhouette, and a front knot accent at the waist. The slinky knit fabric offers a moderate stretch. Complete the look with strappy heels.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Form-hugging silhouette
- Front knot accent at the waist
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4807
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Wonders Square Neck Midi Dress
This sleek midi dress will do wonders for your curves! It features a sleeveless square neckline with bungee spaghetti straps, and a side ruched seam to accentuate your figure along the asymmetrical slit hem. Complete the look in strappy mules for a brunch!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Asymmetrical midi slit hem
- Slinky knit double-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4805
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Draw Attention One-Shoulder Midi Dress
You'll draw all the attention to you in this one-shoulder midi dress perfect for a casual lunch with friends! The dress features a single long sleeve, an adjustable drawstring waist cutout, a side ruched seam, and a form-hugging fit. Complete the look in chic lattice booties.
Fit & Features
- One-shoulder neckline
- Single long sleeve
- Adjustable drawstring waist cutout
- Side ruched seam
- Form-hugging, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4803
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Morning Brew Henley Midi Dress
Serve major looks in the morning slaying it in this midi dress featuring long sleeves, a collared v-neckline, a button-down front, a bodycon silhouette, and a slit hem. Style with a Panama hat and booties!
Fit & Features
- Long sleeves
- Collared v-neckline
- Button-down front
- Bodycon silhouette
- Midi-length slit hem
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4797
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute And Casual Knit Hoodie Dress
This cute and casual knit hoodie dress is perfect for styling up for your weekend plans! It features a hoodie with a front drawstring, long fitted sleeves, and a mini-length, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch for ultra comfortable wear. Complete the look in this short dress with a plaid shacket and combat boots.
Fit & Features
- Hoodie, front drawstring
- Long fitted sleeves
- Mini-length hem
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4798
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chain My Mind Side Slit Midi Dress
This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.
Fit & Features
- Sleeveless square neck
- Chain link adjustable spaghetti straps
- Bodycon silhouette
- Side slit
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4800
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Style Cutout Sweater Dress
Show off a fab trendy style in this long sleeve sweater dress! It features a scoop neckline, a bold cutout at the bust with a tie-front design, dual front cutouts at the waist, and a short, curve-hugging silhouette. The knit fabric offers a moderate stretch. Pair with knee-high boots for a cute everyday 'fit.
Fit & Features
- Long fitted sleeves
- Scoop neckline
- Bust cutout, tie-front design
- Dual front cutouts at the waist
- Mini-length hem, form-hugging fit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1596
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Girl Casual Knit Mini Dress
Show off a cool girl style in this casual knit mini dress! It features a mock neckline with a partial zip-front design, long fitted sleeves, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch for comfortable wear. Complete the look with combat boots.
Fit & Features
- Mock neckline
- Partial zip-front
- Long fitted sleeves
- Mini-length hem, fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4789
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rock Legend Graphic Choker Tunic
Showcase your rock babe status in this edgy graphic tunic top featuring short sleeves, a choker neck with a cutout accent and slash details, and a front script that reads, "Vintage Rock N Roll" along the form-fitting short hem. Complete the look in combat boots for a concert.
Fit & Features
- Short sleeves
- Choker neck with cutout accent
- Slash details
- Graphics front script "Vintage Rock N Roll"
- Form-fitting, short hem
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1414
Category Name: Casual Dresses
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance