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 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
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The Every Day Knit Mini Dress
Keep it cute in a basic mini dress that is perfect to wear any day! The dress features an off the shoulder neckline with a boat neck bust, short sleeves, and composed of a flattering knit fabric. Complete your outfit with sleek stilettos and a cute crossbody.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Boat neckline
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0892
Category Name: Casual Dresses
Price: $9.97 $16.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Pretty In Plaid Woven Mini Dress
Keep it pretty in a plaid dress that is so on trend this season! The dress features a sleeveless square neckline, a plaid print, and a mini length silhouette. Complete your cute date night look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Woven fabric
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 05102-0891
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Timelessly Chic Ribbed Knit Basic Midi Dress
Keep it timelessly chic in a dress that wows! Perfect for a cocktail event or making the right first impression, this mini dress is a must! The dress features a crew neckline with a racer bust, a fitted form-hugging fit, and composed of a ribbed knit fabric. Complete your chic outfit with mules and duster earrings.
Fit & Features
- Sleeveless crew neckline
- Racer bust
- Ribbed knit fabric
- Form hugging fit
- Midi length silhouette
Style Number/Barcode: 05102-0894
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keepin' Knit Simple Ribbed Midi Dress
Keep it simple and stylish in this basic ribbed knit midi dress! It features long fitted sleeves and a mid-length, form-hugging silhouette to enhance your curves. Pair this dress with heeled booties for a casual date night look perf for the cooler months.
Fit & Features
- Long fitted sleeves
- V neckline
- Mid-length, form-fitting style
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0890
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Essential Ribbed Tube Mini Dress
Keep it casual in a tube dress that keeps your look effortlessly on point. The dress features a sleeveless straight neckline and a tube silhouette. Complete look with sneakers and shimmering hoops.
Fit & Features
- Sleeveless square neckline
- Tube silhouette
- Mini length
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0887
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Fall For Floral Woven Midi Dress
Fall head over heels for this adorable ditsy floral midi dress! Featuring a trendy cowl neckline and a flowy mid-length silhouette, this dress would pair perfectly with some simple gold hoops and clear mules. Wear to your next brunch with your girls and you'll receive all the compliments.
Fit & Features
- Adjustable spaghetti straps
- Cowl neckline
- 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: 05102-0882
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruched And Ribbed Knit Crew Neck Mini Dress
This ruched and ribbed knit mini dress is the casual-chic piece you need in your closet! It features a form-hugging fit with ruched detailing to enhance your curves. This dress can be worn as a mini or pulled down and styled as a midi. Wear it with simple slides or elevate the look in heels.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Ruched sides
- Adjustable ties at hem
- Rib-knit, moderate stretch, fits true to size
Style Number/Barcode: 05102-1092
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Live It Up Tie Dye Knit Mini Dress
Live it up in this majorly on-trend tie dye mini dress! Featuring a chic lace-up back and a curve-hugging fit, this dress is perf to make a stylish statement at your next brunch. Simply pair it with some clear mules for a gorgeous look.
Fit & Features
- Scoop neckline
- Spaghetti straps leading to a lace-up back
- Short, form-hugging fit
- Tie dye knit fabric
Style Number/Barcode: 05102-0884
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Major Influence Mock Neck Ruched Mini Dress
Hey, trendsetter! Stun in this mini dress that is so chic and casual! The mini dress features a sleeveless mock neck, a ruched body and a mini length silhouette that hugs curves in all the right places. Style with chunky sneakers to nail those lowkey vibes.
Fit & Features
- Sleeveless
- Mock neck
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0886
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get Knit Right High Slit Maxi Dress
Get your look right in a knit dress that is perfect for keeping it casual! The dress features a sleeveless crew neckline and a maxi length silhouette with a high side slit. Complete your look with chunky sneakers for a cute coffee run outfit.
Fit & Features
- Crew neckline
- Sleeveless
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 05102-0883
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Purrfect Match Leopard Print Tunic
This stylish leopard print tunic will be the purrfect match for you! It features a twist front detail with a tie back, long puff sleeves, and a short hem to elongate your legs. Pair this trendy tunic with some clear heels for an of the moment look.
Fit & Features
- Long puff sleeves
- V neckline
- Twist front detail
- Tie back
- Short hem
- Allover leopard print
- Woven fabric
Style Number/Barcode: 06003-1075
Category Name: Casual Dresses
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keep It Basic Ribbed Mini Dress
Keep your look basic and chic in this ribbed mini dress you can totally dress up or down! It features a mini length silhouette and a form-hugging fit to enhance your curves. Elevate your outfit by pairing this adorable dress with chunky sneakers for a more casual vibe.
Fit & Features
- Bungee spaghetti straps
- Scoop neckline
- Short, form-hugging fit
- Ribbed fabric
Style Number/Barcode: 06002-0611
Category Name: Casual Dresses
Price: $10.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ribbed Knit Crew Neck Maxi Dress
This simple yet stunning ribbed knit maxi dress is a must for your fab fall look. Featuring a high crew neckline and a flattering curve-hugging silhouette, this dress can easily be dressed up with some strappy heels or down with a pair of chunky sneakers. Wear on a casual date night with bae.
Fit & Features
- High crew neckline
- Tank-like shoulder straps
- Form-hugging fit
- Side slit
- Maxi length
- 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: 05102-0870
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Break The Rules Ruched Knit Mini Dress
Dare to bold up your look in a mini dress that showcases curves. The mini dress features a trendy square neckline, fitted long sleeves, and a ruched mini-length silhouette with an envelope hem. Complete look with chunky sneakers for a casual affair.
Fit & Features
- Square neckline
- Long sleeves
- Ruched body
- Mini-length silhouette
- Envelope hem
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0872
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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The Every Day Tube Midi Dress
Step out in this staple dress to wear any day for any occasion! This midi dress is perfect for dressing up with heels to create a night out outfit or dressing down with sneakers for a casual coffee date. The dress features a sleek tube neckline and a midi length silhouette with a mini side slit.
Fit & Features
- Sleeveless straight tube neckline
- Midi length silhouette
- Mini side slit
- Knit fabric
- Form hugging fit
- Moderate stretch
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0827
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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In Knit To Win It Midi Dress
You'll be totally in it to win it in this adorable knit midi dress! It features a double-lined knit fabric and a mid-length, curve-hugging silhouette. Wear this dress with chunky sneakers for an adorable everyday look.
Fit & Features
- Spaghetti straps
- Scoop neckline
- Mid-length form-hugging fit
- Double lined knit fabric
Style Number/Barcode: 05102-0877
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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In Knit For A Good Time Basic Mini Dress
Throw on this basic mini dress and let the good vibes flow! This knit dress is perfect to dress up or dress down for your next date night or for GNO with the squad. The dress features a trendy square neckline, sleek bungee straps, and a mini-length silhouette. Dress up with mules or keep it casual in sneakers.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0873
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale