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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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
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Feelin' Trendy Tie Dye Midi Dress
This trendy tie dye knit midi dress is ready for you to style up! Featuring a sleeveless high neckline and a curve-hugging mid-length silhouette, you can easily take this dress from day to night. Layer on a denim jacket and some chunky sneakers for a casual-chic date look.
Fit & Features
- High rounded neckline
- Mid-length silhouette
- Form-hugging fit
- Tie dye print
- Knit fabric
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0866
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Dream Tie Dye Ruched Mini Dress
You'll look like such a dream in this trendy tie dye mini dress! It features ruched detailing with side ties and a form-fitting style that will hug your curves. Pair this dress with some sleek gold hoops and chunky sneakers for that perf everyday vibe.
Fit & Features
- Crew neckline
- Short sleeves
- Ruched detailing
- Side ties at hem
- Short, form-hugging fit
- Tie dye print
- Knit fabric
Style Number/Barcode: 05102-0867
Category Name: Casual Dresses
Price: $13.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Feelin' Basic V Neck Knit Mini Dress
Sometimes it's a good thing to be basic! This knit mini dress features a deep V neckline and a short, flattering, curve-hugging fit. Keep it casual with some chunky sneakers and gold hoops for a day date with bae.
Fit & Features
- Spaghetti straps
- V neckline
- Square back
- Mini length silhouette
- Double-lined knit fabric
Style Number/Barcode: 05102-0880
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tie Dye Frenzy Brushed Knit Mini Dress
Make a splash in a tie-dye dress that brings the style to your next outing! The mini dress features a round neckline, a slash accent on the left side of the bodice, and a tie-dye print. Style this fun print with chunky sneakers and sleek hoops.
Fit & Features
- Round neckline
- Slashed detail on the left side of the bodice
- Short sleeves
- Tie-dye print
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 06002-0581
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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A Chic Vibe Mini Sweater Dress
Get a major chic vibe in this adorable sweater mini dress! It features a trendy mock neckline, long fitted sleeves, and a short form-hugging fit with a side slit. Pair this dress with over the knee boots for the perf fall date night look.
Fit & Features
- Mock neckline
- Long fitted sleeves with ribbed hems
- Short, form-hugging fit
- Side slit
- Sweater knit fabric
- Moderate stretch
Style Number/Barcode: 06005-0734
Category Name: Casual Dresses
Price: $15.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Tie Front Wrap Mini Sweater Dress
Get an adorable look perfect for a casual date night in this mini sweater dress! It features a wrap front and back with a front tie detail and a short, curve-hugging fit. Pair the dress with chic thigh-high boots for a gorgeous fall-time vibe.
Fit & Features
- Wrap front and back with a V neckline
- Top tie back detail
- Long sleeves with ribbed hems
- Tie front belt
- Short, form-hugging fit
- Sweater knit fabric with plenty of stretch
Style Number/Barcode: 06005-0719
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Ribbed Knit Cutout Mini Dress
Stun in a mini dress that brings sultry appeal with cutout details! The mini dress features an off the shoulder neckline, cutout detail at the bust with matching cutout detail at the midriff, and a mini length silhouette. Complete look with clear mules.
Fit & Features
- Off the shoulder neckline
- Cutout detail at the bust
- Cutout detail at the midriff
- Long sleeves
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0864
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Get On-Trend Tie Dye Knit Mini Dress
Get on-trend in this adorable tie dye knit mini dress! It features an open back detail with a tie closure and ruched, form-hugging fit to enhance your curves. Pair this dress with chunky sneakers for a casual-chic everyday look.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Open back detail with tie closure
- Ruched detailing
- Short, form-hugging fit
- Tie dye knit fabric
Style Number/Barcode: 05102-0861
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Good Vibes Basic Ribbed Knit Maxi Dress
Bring the good vibes in a maxi dress that can be dressed up for a chic day out. The dress features a scoop neckline, sleek bungee straps, and a maxi length silhouette with a high side slit. Style dress with chunky sneakers and sleek hoops.
Fit & Features
- Sleeveless scoop neckline
- Bungee spaghetti straps
- Maxi length silhouette
- High side slit
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0863
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance