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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Trendy Twist Knot Open Back Ribbed Mini Dress
Stun in a dress that makes them take a double-take with bold details! The dress features a crew neckline, fitted long sleeves, and a stunning open back with a twist knot bar strap accent. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Crew neckline
- Fitted long sleeves
- Open back
- Twist knot bar strap
- Ribbed knit fabric
- Mini length silhouette
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0991
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ribbed Knit O-Ring Mini Dress
Keep it chic in a ribbed knit dress that has a stylish twist! The mini dress features a trendy crew neckline, an O-ring accent with waist cutouts, and composed of a ribbed knit fabric that embraces curves. Complete look with clear mules for a head-turning look.
Fit & Features
- Crew neckline
- O-ring accent with waist cutouts
- Fitted long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form-hugging fit
Style Number/Barcode: 05102-0998
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slay In Basics Ribbed Knit Mini Dress
Slay in a basic mini dress that is perfect for a casual date night. The dress features a mock neck, long sleeves, and a rounded mini length hem. The dress is composed of a ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Mock neck
- Long sleeves
- Rounded mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0852
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Chic Cutout Midi Dress
Keep it chic with a midi dress that brings all the appeal. The dress features a sleeveless scoop neckline, a midriff cutout, spaghetti straps, a mini-length silhouette with a midi length overlay. The dress is composed of a ribbed knit fabric that offers a form-hugging fit. Complete look with wedges.
Fit & Features
- Sleeveless scoop neckline
- Midriff cutout
- Spaghetti straps
- Mini length silhouette with overlay
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0995
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The One Basic One Shoulder Ribbed Mini Dress
This ribbed dress is the one that you can't live without! Dress up this beauty with duster earrings and mules for a glam night out outfit. The dress features a one-shoulder neckline, a ruched mini length silhouette, and composed of a ribbed knit fabric.
Fit & Features
- Sleeveless bodice
- One-shoulder neckline
- Ruched body
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0997
Category Name: Casual Dresses
Price: $10.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Twist Back Ribbed Knit Midi Sweater Dress
Keep your look on point and trendy in this chic twist back knit sweater dress! Featuring a partially open back and a mid-length, curve-hugging silhouette, this dress is perfect for the fall season. Dress it up with statement earrings for a cute fall date night.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Open back with twist back detail
- Mid-length silhouette
- Form-hugging fit
- Ribbed sweater knit fabric
Style Number/Barcode: 06005-0846
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Effortlessly Chic Sleeveless Mini Dress
You'll look so effortlessly chic in this simple yet stylish mini dress! It features a sleeveless bodice, a high neckline, and a mini length, curve-hugging silhouette. The knit fabric is lined and offers plenty of stretch for comfortable wear. Pair this dress with a denim jacket for a casual look or a blazer for an elevated vibe.
Fit & Features
- High neckline
- Short, form-hugging fit
- Lined knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0994
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Brushed Knit Sleeveless Crew Neck Midi Dress
Slip into this adorable sleeveless midi dress for a chic everyday look! It features a crew neckline and a mid-calf length, curve-hugging silhouette. The brushed knit fabric has a soft cashmere-like feel. Pair this dress with chunky sneakers for a casual vibe or heeled booties for a date night.
Fit & Features
- Crew neckline
- Tank-like shoulder straps
- Mid-length, form-hugging fit
- Brushed knit fabric
Style Number/Barcode: 05102-0984
Category Name: Casual Dresses
Price: $15.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleeveless Shaggy Knit Mini Dress
Keep it chic in a shaggy knit dress that brings flair to your wardrobe. The dress features a sleeveless scoop neckline, tank straps, and a mini length silhouette. The dress is composed of an unlined shaggy knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with clear mules.
Fit & Features
- Sleeveless scoop neckline
- Tank straps
- Mini length silhouette
- Shaggy knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0982
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Need For Basics Ribbed Midi Dress
Get your need for basics in a dress that can be dressed up or dressed down for your next day out. The dress features a trendy square neckline, tank-like straps, and a midi length silhouette. Complete your look with clear heels and statement hoop earrings.
Fit & Features
- Sleeveless square neckline
- Tank-like straps
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0871
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stylish Babe Scoop Neck Mini Dress
You'll be a total stylish babe in this chic mini dress! It features a wide scoop neckline, long fitted sleeves, and a curve-hugging, mini length silhouette. The dress is composed of a brushed knit fabric with plenty of stretch for comfortable wear. Pair this dress with thigh-high boots to elevate it to a night out look!
Fit & Features
- Wide scoop neckline
- Long fitted sleeves
- Short, form-hugging fit
- Brushed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0986
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tied to Basics Ribbed Knit Scoop Neck Mini Dress
Get tied to basics in a ribbed mini dress that is oh too gorgeous! The dress features a scoop neckline, tie spaghetti straps, and composed of a ribbed knit fabric that hugs curves in all the right places. Complete your casually cute look with stud earrings and block heels.
Fit & Features
- Scoop neckline
- Tie spaghetti straps
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0978
Category Name: Casual Dresses
Price: $7.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Basic Side Slit Ribbed Knit Mini Dress
Amp up your basic mini dress with a trendy side slit! This staple piece dress features a mock neck, long sleeves, and a side slit. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties.
Fit & Features
- Mock neck
- Long sleeves
- Side slit
- Mini length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0966
Category Name: Casual Dresses
Price: $16.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Gorgeous Girl Faux Wrap Front Ribbed Mini Dress
You'll look oh so gorgeous in this wrap front ribbed mini dress! Featuring a deep V neckline and a ribbed knit fabric that will hug your curves, this dress is perf for a night out. Pair with some large hoop earrings and heels to complete the vibe.
Fit & Features
- Bungee spaghetti straps
- Deep V neckline
- Faux wrap front with asymmetric hem
- Ruched detailing
- Short, form-hugging fit
- Ribbed knit fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0818
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Open Back Ruched Ribbed Knit Midi Dress
Style up this basic ribbed knit midi dress for the perfect everyday look! It features a partial lower open back, ruched detailing and a curve-hugging mid-length silhouette. Pair the dress with chunky sneakers to get that casual, cute vibe.
Fit & Features
- Scoop neckline
- Long fitted sleeves
- Partial lower open back
- Ruched detailing
- Form-hugging fit
- Midi length
- Ribbed knit fabric
Style Number/Barcode: 05102-0977
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Crush Cozy Mini Dress
You'll absolutely love this cozy crush-worthy mini dress! It features an off the shoulder fold-over neckline, long blouson sleeves with tapered hems, and a mini length, curve-hugging silhouette. The lightweight knit fabric has a cashmere-like feel and offers plenty of stretch. Pair this dress with thigh-high boots for the perf holiday look.
Fit & Features
- Off the shoulder fold-over neckline
- Long blouson sleeves
- Short, form-hugging fit
- Soft knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0970
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stunning Mesh Mini Dress
Keep it Stunning in a chic mini dress, babe! The dress features a sleeveless square neckline, bungee-corded straps, and a curve-hugging mini-length silhouette. Complete the look with chic mules.
Fit & Features
- Sleeveless square neckline
- Corded shoulder straps
- Mini-length silhouette
- Sheer mesh fabric, full knit lining
- Form-hugging fit
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0976
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keepin' Knit Chic Midi Sweater Dress
Keep it chic and stylish in this knit midi sweater dress, a perf transitional piece into the new season! It features a curve-hugging fit and a mid-length silhouette. Pair the dress with some trendy heeled booties for that must-have fall look.
Fit & Features
- V neckline
- Tank-like shoulder straps
- Mid-length silhouette
- Form-hugging fit
- Ribbed sweater knit fabric
Style Number/Barcode: 06005-0832
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cut To The Chase Knit Mini Dress
Let's cut to the chase - this knit mini dress is so chic! Featuring trendy cut outs and a sexy, curve-hugging fit, this dress is perf for a girl's night out. Pair it with chunky gold hoops to give the look some glam.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Waist cut out
- Ruched detailing
- Short, form-hugging fit
- Knit fabric with plenty of stretch
Style Number/Barcode: 05102-0974
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Own Knit Ruched Mini Dress
Own your gorgeous look in this adorable knit mini dress! It features a trendy mock neckline, ruched detailing down the back, and a sexy curve-hugging fit. Pair this dress with some chic heels for a night out.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Open back
- Ruched back detailing
- Short, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-0971
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Slaying Knit Sleeveless Ribbed Midi Dress
Slay it in a ribbed knit dress that stuns for your next date night in! The dress features a sleeveless square neckline, sleek bungee straps, and a curve-hugging midi-length silhouette. Complete look with clear mules.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0964
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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The Every Day Ribbed Knit Midi Dress
This knit dress is perfect for your everyday occasions! Layer with chunky sneakers and dainty rings to create a chic back to school outfit this season. The dress features a mock neck, long sleeves, a midi-length silhouette, and composed of a soft to the touch ribbed knit fabric that enhances curves.
Fit & Features
- Mock neck
- Long sleeves
- Midi length silhouette
- Lined ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0960
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Flowy Floral Woven Midi Dress
Create an effortlessly pretty look in this floral woven midi dress! It features a trendy tie front detail and a flattering flowy mid-length silhouette. Pair the dress with block heels and gold hoops for the perfect date night outfit.
Fit & Features
- V neckline
- Tie front detail
- Three-quarter length flowy sleeves
- Front waist cut out
- Mid-length flowy fit
- Floral printed woven fabric
Model is 5'7" with a 32.5" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0962
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Vibes Button Down Ribbed Mini Dress
Rock a basic mini dress to layer with your favorite denim jacket or moto jacket this season. The dress features a crew neckline, a button-down front, long sleeves, and a mini length silhouette with a raw edge hem. The dress is composed of a ribbed knit fabric.
Fit & Features
- Crew neckline
- Button-down front
- Long sleeves
- Mini length silhouette, raw edge hem
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0955
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance