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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Sporty-Chic Long Sleeve Mini Dress
Give your everyday look a sporty-chic vibe by styling up this adorable mini dress! It features long fitted sleeves, a mock neckline with a partial zip front, and a short, form-hugging fit. Pair this dress with chunky sneakers to casually slay your 'fit!
Fit & Features
- Long fitted sleeves
- Mock neckline
- Partial zip front
- Mini length
- Curve-hugging silhouette
- Double-lined brushed knit fabric
- Plenty of stetch
Style Number/Barcode: 05102-0930
Category Name: Casual Dresses
Price: $12.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Everyday Ruched Knit Mini Dress
Get an effortless everyday 'fit in this adorable ruched knit mini dress! It features trendy ruched detailing with drawstrings and can be worn as a mini or midi. Dress it up with clear mules for a date night or keep it casual with some chunky sneakers for a shopping trip.
Fit & Features
- Tank-like shoulder straps
- High rounded neckline
- Ruched detailing
- Drawstrings at hem
- Form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-1018
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off the Shoulder Long Sleeve Mini Dress
Stun in a basic off the shoulder dress that keeps it casual and cute. The dress features an off the shoulder neckline, long ruched sleeves, and a mini length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with plenty of stretch. Complete the look with clear mules.
Fit & Features
- Off the shoulder neckline
- Long ruched sleeves
- Mini length silhouette
- Knit fabric
- Form-hugging fit
- Plenty of stretch
Style Number/Barcode: 05102-0937
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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All Buttoned Up Off The Shoulder Midi Dress
Get all buttoned up in this adorable off the shoulder midi dress! It features a complete button-down front with a curve-hugging, mid-length fit. Perfect for everyday, pair this dress with heeled booties to take your look into fall.
Fit & Features
- Off the shoulder neckline
- Short fitted sleeves
- Complete button-down front
- Mid-length, form-hugging fit
- Ribbed knit fabric
Style Number/Barcode: 05102-0943
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stunning Snake Print Mesh Mini Dress
Stun in a trendy snake print dress that makes a stylish statement! Throw this dress on with your favorite black heels for your next GNO. The dress features a sleeveless square neckline, sleek bungee straps, and a snake print. The dress is composed of mesh fabric that offers a form hugging fit with a moderate stretch.
Fit & Features
- Sleeveless square neckline
- Bungee straps
- Snake print
- Mini length silhouette
- Mesh fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0936
Category Name: Casual Dresses
Price: $6.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Trendy Ribbed Mini Dress
Keep it trendy in a ribbed mini dress that is perfect for nails those casual vibes! The dress features a square neckline, long sleeves, and a mini length silhouette. The dress is composed of a ribbed knit fabric that offers a form hugging fit that offers a moderate stretch. Complete your look with chunky sneakers.
Fit & Features
- Square neckline
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
- Double lined
Style Number/Barcode: 05102-0940
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Chic Ruched Knit Mini Dress
Keep it totally chic in a ruched mini dress! The dress features an off the shoulder neckline, long fitted sleeves, and a ruched drawstring center. The dress is composed of a ribbed knit fabric that hugs curves in all the right places. Complete look with sneakers for a casual look.
Fit & Features
- Off the shoulder neckline
- Long fitted sleeves
- Ruched drawstring center
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0932
Category Name: Casual Dresses
Price: $14.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple And Sleek Tie Shoulder Slip Dress
Simple and sleek, this slip dress is a gorgeous piece you need to have in your closet. Featuring tie shoulder straps and a flowy mid-length silhouette, it can so easily be dressed up with some clear mules or down with chunky sneaks. Wear to your next date with bae and you'll leave a lasting impression.
Fit & Features
- Tie shoulder straps
- Slight V neckline
- Square back
- Flowy mid-length fit
- Woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0895
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keeping Knit Casual Ribbed Mini Dress
Keep it cute and casual in a wrap mini dress that is perfect for dinner with the squad. The dress features an off the shoulder neckline, long Dolman sleeves, a bar strap accent at the back, a cinching tie waist belt, 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.
Fit & Features
- Off the shoulder neckline
- Bar strap at the back
- Long Dolman sleeves
- Tie waist belt with belt loops
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 06005-0804
Category Name: Casual Dresses
Price: $24.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Basic Vibes Knit Midi Dress
Rock those basic vibes in a dress that keeps it comfortable and chic. The everyday dress features a sleeveless bodice, a v-neckline with notched detail, and a midi length silhouette. Complete your look with chunky sneakers and a chunky necklace to create a trendy streetwear look.
Fit & Features
- Sleeveless bodice
- V-neckline with notched detail
- Midi length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0924
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Basic Midi Dress
Bring it back to basics in a ribbed dress that showcases your curves in all the right places. The dress features a scoop neckline, long sleeves, 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 ankle booties.
Fit & Features
- Scoop neckline
- Long sleeves
- Midi length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 06005-0800
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flirty Floral Polka Dot Mini Dress
Create a flirty first impression in this pretty floral polka dot mini dress! It features a cowl neckline, a flowy mini length silhouette, and a fun floral print on a polka dot woven fabric. For a cute day date look, layer on a denim jacket and pair with some clear heels.
Fit & Features
- Adjustable spaghetti straps
- Cowl neckline
- Flowy mini length fit
- Floral print
- Polka dot woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0914
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Flair Woven Midi Dress
You'll have that total floral flair in this stunning woven midi dress! Featuring a V neckline and a flowy mid-length silhouette, this dress would be perfect for a fall date night. Pair with some clear heels and accessorize with gold hoops to let the dress make the statement.
Fit & Features
- Adjustable spaghetti straps
- V neckline
- Back zipper closure
- Flowy mid-length fit
- Ditsy floral print
- Woven fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0915
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Feline Fashionista Leopard Mesh Mini Dress
Keep it fierce in a leopard dress that shows off your affinity for style! The mini dress features a leopard print, a sleeveless square neckline, and sleek spaghetti straps. Complete your night-out look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Leopard print pattern
- Mini-length silhouette
- Lined mesh fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-0927
Category Name: Casual Dresses
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Keeping Knit Real Ruched Mini Dress
Keep it real in this chic mini dress for your next outing with the squad! The dress features a crew neckline, ruched side seams with drawstrings at the hem, and a curve-hugging mini-length silhouette. Complete your look with mules.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched side seams
- Drawstrings at the hem
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
Style Number/Barcode: 05102-0921
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Brushed Knit Mini Dress
Elevate your everyday style with this adorable brushed knit mini dress! It features an off the shoulder fold-over neckline with long fitted sleeves and a short, curve-hugging silhouette. Pair this dress with heeled booties for the perf winter date night with bae.
Fit & Features
- Off the shoulder fold-over neckline
- Long fitted sleeves
- Short, form-hugging fit
- Stretchy ribbed brushed knit fabric
- Stretchy knit lining
- Merrow edge hems
Style Number/Barcode: 05102-0917
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Must-Have Ribbed Knit Mini Dress
This must-have ribbed knit mini dress needs to be in your closet this season! It features a mock neckline, long fitted sleeves, a short, form-hugging fit, and a cute merrow edge trim. Pair this dress with chunky sneakers for a casual 'fit to hang with the squad.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Mini length silhouette
- Curve-hugging fit
- Ribbed knit fabric with plenty of stretch
- Merrow edge trim
Style Number/Barcode: 05102-0928
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Trendy Girl Turtleneck Mini Dress
Hey trendy girl! Style up this adorable turtleneck mini dress for a cozy-chic look! It features long fitted sleeves, a short, curve-hugging silhouette, and viscose crepe fabric with plenty of stretch for comfortable wear. Pair this dress with chunky sneakers for an effortless everyday 'fit.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Short, form-hugging fit
- Viscose crepe fabric with a lining
- Plenty of stretch
Style Number/Barcode: 05102-0956
Category Name: Casual Dresses
Price: $6.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Lovin' The Basics Cotton Midi Dress
You'll be lovin' everything about this basic cotton midi dress! Featuring a crew neckline and a mid-length, curve-hugging fit, this dress will flatter your figure. Pair with some gold hoops and chunky sneakers for a laid back, casual vibe you can wear to hang out with your squad.
Fit & Features
- Crew neckline
- Short sleeves
- Mid-length silhouette
- Cotton fabric
Style Number/Barcode: 05102-0926
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Slay Every Day Basic Scoop Neck Midi Dress
Slay every day in a basic midi dress that is effortlessly chic. The dress features a sleeveless scoop neckline, tank-straps, and a midi length silhouette. The double lined smooth knit fabirc offers a comfortable feel. Complete your look with chunky sneakers and stud earrings to nail low-key vibes.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Midi length silhouette
- Double lined smooth knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0908
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Majorly Chic Turtleneck Midi Dress
Give your workwear look a majorly chic vibe when you wear this must-have midi dress! It features a sleeveless bodice, a trendy turtleneck, and a mid-length, curve-hugging silhouette. Layer on an oversized blazer and style with strappy heels for the perfect outfit for the office.
Fit & Features
- Sleeveless bodice
- Turtleneck
- Mid-length
- Form-hugging fit, moderate stretch
- Viscose crepe fabric
- Double-lined
Style Number/Barcode: 05102-0911
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Keeping Knit Chic Mock Neck Ruched Mini Dress
Keep it chic in a ruched dress that elevates your night out outfit! The dress features a mock neck, fitted long sleeves, and a ruched side drawstring. Complete your night out look with clear heels.
Fit & Features
- Mock neck
- Fitted long sleeves
- Ruched side drawstring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0904
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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What's The Scoop Cutout Ribbed Knit Mini Dress
Serve up a chic look in the ribbed dress! Perfect for your next brunch date, this mini dress brings the drama! The dress features a scoop neckline with shoulder cutouts, tank-like straps, and a mini length silhouette. Style dress with a fab top knot and door knocker earrings.
Fit & Features
- Scoop neckline with tank-like straps
- Shoulder cutouts
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0903
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Classic Chic Scoop Neck Knit Mini Dress
Fall in love with the classic chic look of this adorable basic knit mini dress! It features bungee spaghetti straps and a short, flattering, curve-hugging fit. This dress can easily be dressed up with heels for date night or kept more casual with a bucket hat and chunky sneakers for a shopping day.
Fit & Features
- Bungee spaghetti straps
- Scoop neckline
- Mini-length silhouette
- Knit fabric
- Runs true to size
Style Number/Barcode: 05102-0897
Category Name: Casual Dresses
Price: $9.97 $18.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale