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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Trendsetting Stunner Slinky Knit Midi Dress
Show off your trendy stunner status in this of-the-moment slinky knit midi dress. It features a collared neckline, long sleeves, a complete button-down front, ruching at the waist, and a mid-length, curve-hugging silhouette. Complete the look with sleek hoop earrings.
Fit & Features
- Collared neckline
- Long fitted sleeves
- Complete button-down front
- Ruching at the waist
- Mid-length, form-hugging fit
- Slinky knit fabric
- Runs true to size
Style Number/Barcode: 05102-4222
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring On Basics Sleeveless Midi Dress
Bring on those basic vibes with a dress that is perf for every day! The dress features a sleeveless V-neckline, tank shoulder straps, and a midi-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless V-neckline
- Tank shoulder straps
- Midi-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4221
Category Name: Casual Dresses
Price: $32.90
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Chic Button Front Tunic
Create an effortlessly chic everyday look with this classic tunic. It features a collared neckline, a complete button-down front, long sleeves, and a cinched waist effect for a figure-flattering silhouette. Style this tunic with sleek hoops and clear mules.
Fit & Features
- Collared neckline
- Button-down front
- Long sleeves, single-button details
- Cinched waist effect
- Pleating detail
- Woven fabric, no stretch
- Runs true to size
Style Number/Barcode: 06003-1497
Category Name: Casual Dresses
Price: $18.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Such A Showstopper Mini Dress
You'll be such a showstopper in this sassy-chic mini dress. It features an on-trend mock neckline, long sleeves, side ruched detailing with an adjustable tie, and a short, curve-hugging fit. The lightweight stretchy knit fabric showcases a fab all-over snake print. Style this dress with black thigh-high boots.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Side ruching, adjustable drawstring at the hem
- Mini-length, form-fitting silhouette
- Stretchy knit fabric, snake print
- Runs true to size
Style Number/Barcode: 05102-4215
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stun In Snake Print Button-Down Dress
Make a stunning appearance in this snake print dress! It features long sleeves, a collared v-neck, a button-down front with ruching to flaunt your figure, and a fitted hem. Complete your look with a boater hat and heels.
Fit & Features
- Long sleeves, collared v-neck
- Snake print
- Button-down with ruching
- Short, fitted hem
- Smooth knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4216
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple And Sexy High-Slit Midi Dress
Simple and sexy, this ribbed cotton midi dress can be dressed up or down. It features a sleeveless crew neckline, tank shoulder straps that lead to a cross-back design, a high side slit, and a mid-length, curve-hugging silhouette. Style this dress with sandals to keep it casual, or heels for a chic vibe.
Fit & Features
- Sleeveless crew neckline
- Tank shoulder straps
- Open back, cross-back design
- High side slit
- Mid-length, form-hugging fit
- Ribbed cotton fabric, lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4213
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make A Seam Ribbed Knit Mini Dress
Create a stylish scene with a dress that brings major exposure! The dress features a square neckline, long sleeves, exposed vertical seams that create an hourglass effect, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and hoops.
Fit & Features
- Square neckline
- Long sleeves
- Exposed vertical seams
- Mini length silhouette
- Ribbed knit-lined fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4214
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Born To Ride Lace Up Mini Dress
Let this mini dress let everyone know that you were born to be wild! The dress features a crew neckline, a plunging keyhole at the bodice, a chain-link lace-up front, short sleeves, and a mini-length silhouette. The dress features a graphic that reads: "Riders, Motorcycle" with an image of eagle wings. The dress is composed of a cotton knit fabric. Complete look with sneakers.
Fit & Features
- Crew neckline
- Keyhole at bodice
- Chain link lace-up front
- Short sleeves
- Mini length silhouette
- Graphic: "Riders, Motorcycle", image of eagle wings
- Form hugging fit, moderate stretch
Style Number/Barcode: 06002-0944
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get A Clue Plaid Blazer Dress
Showcase a trendy look with this effortlessly fab dress that will give you an all-in-one outfit! It features a blazer-designed top with a V-neckline and a lapel collar, shoulder pads, long sleeves, a dual snap-button front, a waist cutout, and a short fitted skirt with a high waist and a faux button-down design. The plaid woven fabric has a smooth lining and no stretch. Pair this dress with strappy mules.
Fit & Features
- Blazer-designed top
- V-neckline, lapel collar
- Shoulder pads, long sleeves
- Dual snap-button front
- Waist cutout, hidden side zipper closure
- Short fitted skirt, high waist, faux button-down design
- Woven fabric, smooth lining, no stretch, plaid print
- Runs true to size
Style Number/Barcode: 05102-4209
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Baddie Chic Tie Front Mini Dress
Rock on like the baddie you are with a tie-front mini dress that is part edgy, part chic! The dress features a plunging V-neckline, short sleeves, a sexy tie-front, cutout at the midriff, and a mini-length silhouette. The dress features an image of eagle wings, roses, and a script that reads: "American Motorcycles. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with chunky sneakers.
Fit & Features
- Plunging V-neckline, short sleeves
- Tie-front, cutout at the midriff
- Mini length silhouette
- Image of eagle wings, roses
- Script: "American Motorcycles"
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-0943
Category Name: Casual Dresses
Price: $10.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Status Strapless Midi Dress
Elevate your chic status with this simple yet stunning midi dress. It features a strapless square neckline, a high waist seam, a mid-length, curve-hugging silhouette, and a sultry side slit. Style this dress with strappy heels for a night out.
Fit & Features
- Strapless square neckline
- High waist seam
- Mid-length, form-hugging fit
- Side slit
- Runs true to size
Style Number/Barcode: 05102-4210
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Moves Mesh Mini Dress
Make stylish trendy moves in this must-have mesh mini dress. It features a sleeveless square neckline, spaghetti straps, side ruching, and a short, curve-hugging silhouette. The sheer mesh fabric has a full knit lining and showcases an all-over subtle zebra print. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Back zipper and hook and eye closure
- Side ruching, mini-length, form-fitting silhouette
- Sheer mesh fabric, full knit lining, moderate stretch
- Zebra print
- Runs true to size
Style Number/Barcode: 05102-4211
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Basic Long Sleeve Mini Dress
This ribbed cotton mini dress is a chic basic you need in your closet! It features a crew neckline, long fitted sleeves, and a short, curve-hugging silhouette. Style this dress with cute booties.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Ribbed cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4208
Category Name: Casual Dresses
Price: $11.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Totally Tie-Dye Mock Neck Dress
You'll tie-dye for this mock neck dress featuring long sleeves and a mini-length hem. The dress is composed of a ribbed knit fabric with a moderate stretch. Style with edgy booties.
Fit & Features
- Long fitted sleeves
- Mock neckline
- Tie-dye pattern
- Bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4206
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Extra Extra Newspaper Print Mini Dress
You'll be the talk of the town babe in this eye-catching mini dress! It's designed with a unique newspaper print, ruched tie sides, and thin spaghetti straps. Wear it with hoops and lace-up heels to be tomorrow's front page news!
Fit & Features
- Bodycon fit with moderate stretch
- Thin spaghetti straps
- V-neckline
- Ruched sides with ties
- Brushed knit fabric, newspaper print
- Runs true to size
Style Number/Barcode: 05102-4203
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendy Stunner Plaid Mini Dress
You'll be a total trendy stunner in this sultry sleeveless plaid mini dress! It features a square neckline, spaghetti straps, an open back with a strappy design, and a short, curve-hugging silhouette. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, strappy design
- Mini-length, form-hugging fit
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4205
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simply Stylish Mock Neck Mini Dress
Simply stylish, this basic mini dress is a must-have you can dress up or down! It features a mock neckline, long fitted sleeves, and a short, form-hugging fit. The lightweight cotton fabric offers a moderate stretch. Layer on a faux leather shacket and complete the look with ankle booties.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Cotton fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4200
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Trendsetter Ruched Knit Mini Dress
Showcase casual trendsetting looks in this stylish knit mini dress. It features a square neckline, short sleeves, ruched side detailing with drawstrings, and a short, form-hugging silhouette. Pair this dress with a denim jacket and cute mules for an effortless everyday outfit.
Fit & Features
- Square neckline
- Short sleeves
- Ruched side detailing
- Adjustable drawstrings
- Mini-length, form-hugging fit
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4333
Category Name: Casual Dresses
Price: $4.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Dose Of Style Knit Mini Dress
Serve up major style with a mini dress that is perf for a chic layered outfit. The dress features a mock neck, long sleeves, a ruched drawstring, and a mini-length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a trench coat and boots.
Fit & Features
- Mock neck
- Long sleeves
- Ruched drawstring
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4199
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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So Sophisticated Collared Midi Dress
Keep your look sleek and sophisticated in a midi dress that's a major staple! The dress features a collared neckline, long sleeves, a side slit, 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 look with a plaid coat and ankle booties.
Fit & Features
- Collared neckline
- Long sleeves
- Side slit
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4197
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Chic Ditsy Floral Mini Dress
Bring the charm with a floral mini dress that is perf for date night! The dress features a sleeveless sweetheart neckline with a lace trim, spaghetti straps, a ditsy floral print, 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 wedges.
Fit & Features
- Sleeveless sweetheart neckline, lace trim
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, lace trim at the hem
- Smooth knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4196
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Start A Spark Ruched Mini Dress
Start a spark with a mini dress that showcases your luxe style! The dress features a sleeveless square neckline, bungee spaghetti straps, a ruched body, and a mini-length silhouette. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with lucite heels and gold jewelry.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Ruched body
- Mini length silhouette
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4191
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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On That Retro Vibe Colorblock Mini Dress
Channel those retro vibes with this fab mini dress! The dress features a colorblock pattern, a crew neckline, long sleeves, a cutout at the midriff with criss-cross straps, dual ruched drawstrings at the hem, and a mini-length silhouette. 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
- Colorblock pattern
- Crew neckline
- Long sleeves
- Cutout at midriff, criss-cross straps
- Dual ruched drawstrings
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4192
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Essential Ribbed Knit Midi Dress
This ribbed knit midi dress is a basic essential you need in your closet that you can dress up or down. It features a sleeveless square neckline, spaghetti straps, a mid-length, curve-hugging silhouette, and a stylish side slit. Keep this dress casual with sneakers, or elevate the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Form-hugging fit
- Side slit, midi-length hem
- Double-lined rib knit fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4961
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free