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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Of-The-Moment Chic Swirl Print Midi Dress
This of-the-moment chic swirl print midi dress is perf for happy hour! It features a sleeveless V-neckline, bungee spaghetti straps, a hip-hugging fit that flows out to a midi-length A-line silhouette, and a sultry front slit. The smooth jersey knit fabric showcases an alluring all-over swirl print pattern. Style with a faux leather blazer and strappy stilettos.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Hip-hugging fit, midi-length A-line silhouette
- Thigh-high front slit
- Swirl print pattern
- Jersey knit fabric, lined bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4817
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Always Cozy Turtleneck Mini Dress
You'll forever be cozy in this soft and stretchy brushed knit mini dress! It features a turtleneck, long fitted sleeves, and a short, curve-hugging, bodycon silhouette. Style with a plaid blanket scarf and knee-high boots.
Fit & Features
- Turtleneck
- Long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Double-lined brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4811
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Laced Up For The Night Mini Dress
Heat up the night in this bombshell sleeveless mini dress featuring v-neckline, tank-style straps, a bodycon silhouette, and a cutout side with lace-up straps. Perfect for styling with strappy stiletto heels.
Fit & Features
- Sleeveless v-neckline
- Tank-style straps
- Bodycon silhouette
- Cutout side with lace-up straps
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4814
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cream Of The Crop Cutout Mini Dress
Look and feel your absolute best in this prize-worthy casual mini dress! It features a sleeveless, one-shoulder neckline with a thin shoulder strap, a sultry cutout waist with a hoop insert, and a bodycon silhouette. Complete the look in clear strap heels for a lunch date.
Fit & Features
- Sleeveless, one-shoulder neckline
- Thin shoulder strap
- Cutout waist, hoop insert
- Bodycon silhouette
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4806
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knot Pleasure Crew Neck Midi Dress
This crew neck midi dress will be pleased to be added to your fashion closet! It features long fitted sleeves, a form-hugging silhouette, and a front knot accent at the waist. The slinky knit fabric offers a moderate stretch. Complete the look with strappy heels.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Form-hugging silhouette
- Front knot accent at the waist
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4807
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Wonders Square Neck Midi Dress
This sleek midi dress will do wonders for your curves! It features a sleeveless square neckline with bungee spaghetti straps, and a side ruched seam to accentuate your figure along the asymmetrical slit hem. Complete the look in strappy mules for a brunch!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Asymmetrical midi slit hem
- Slinky knit double-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4805
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Draw Attention One-Shoulder Midi Dress
You'll draw all the attention to you in this one-shoulder midi dress perfect for a casual lunch with friends! The dress features a single long sleeve, an adjustable drawstring waist cutout, a side ruched seam, and a form-hugging fit. Complete the look in chic lattice booties.
Fit & Features
- One-shoulder neckline
- Single long sleeve
- Adjustable drawstring waist cutout
- Side ruched seam
- Form-hugging, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4803
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Morning Brew Henley Midi Dress
Serve major looks in the morning slaying it in this midi dress featuring long sleeves, a collared v-neckline, a button-down front, a bodycon silhouette, and a slit hem. Style with a Panama hat and booties!
Fit & Features
- Long sleeves
- Collared v-neckline
- Button-down front
- Bodycon silhouette
- Midi-length slit hem
- Soft knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4797
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute And Casual Knit Hoodie Dress
This cute and casual knit hoodie dress is perfect for styling up for your weekend plans! It features a hoodie with a front drawstring, long fitted sleeves, and a mini-length, form-hugging fit. The soft ribbed knit fabric offers plenty of stretch for ultra comfortable wear. Complete the look in this short dress with a plaid shacket and combat boots.
Fit & Features
- Hoodie, front drawstring
- Long fitted sleeves
- Mini-length hem
- Form-hugging fit
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4798
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chain My Mind Side Slit Midi Dress
This knit midi dress will change your mind about going out for the night! Catch all the attention in this sultry dress featuring a sleeveless square neck, chain link adjustable spaghetti straps, a bodycon silhouette, and a side slit. Complete the look with a bold clutch purse.
Fit & Features
- Sleeveless square neck
- Chain link adjustable spaghetti straps
- Bodycon silhouette
- Side slit
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4800
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Trendy Style Cutout Sweater Dress
Show off a fab trendy style in this long sleeve sweater dress! It features a scoop neckline, a bold cutout at the bust with a tie-front design, dual front cutouts at the waist, and a short, curve-hugging silhouette. The knit fabric offers a moderate stretch. Pair with knee-high boots for a cute everyday 'fit.
Fit & Features
- Long fitted sleeves
- Scoop neckline
- Bust cutout, tie-front design
- Dual front cutouts at the waist
- Mini-length hem, form-hugging fit
- Sweater knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1596
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cool Girl Casual Knit Mini Dress
Show off a cool girl style in this casual knit mini dress! It features a mock neckline with a partial zip-front design, long fitted sleeves, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch for comfortable wear. Complete the look with combat boots.
Fit & Features
- Mock neckline
- Partial zip-front
- Long fitted sleeves
- Mini-length hem, fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4789
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Rock Legend Graphic Choker Tunic
Showcase your rock babe status in this edgy graphic tunic top featuring short sleeves, a choker neck with a cutout accent and slash details, and a front script that reads, "Vintage Rock N Roll" along the form-fitting short hem. Complete the look in combat boots for a concert.
Fit & Features
- Short sleeves
- Choker neck with cutout accent
- Slash details
- Graphics front script "Vintage Rock N Roll"
- Form-fitting, short hem
- Jersey knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1414
Category Name: Casual Dresses
Price: $12.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Preppy Spirit Collared Midi Dress
Get some pep in your step by styling this casual midi dress for art shows or family dinners! The mid-length dress features a collared V-neckline, long fitted sleeves, and a bodycon silhouette on stretchy ribbed knit fabric. Style with knee-high boots to complete the look!
Fit & Features
- Collared V-neckline
- Long fitted sleeves
- Bodycon silhouette
- Midi-length hem
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4785
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Bae Crew Neck Slit Maxi Dress
A cute basic maxi dress for looking trendy on your off-duty days! It features short sleeves, a crew neck, a bodycon silhouette, and a high side slit to show off some leg! The dress is composed of a brushed knit stretchy fabric. Complete the look in flat sandals and a handbag.
Fit & Features
- Short sleeves
- Crew neck
- High side slit
- Bodycon silhouette
- Maxi-length hem
- Brushed knit stretchy fabric
- Runs true to size
Style Number/Barcode: 05102-4786
Category Name: Casual Dresses
Price: $18.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Minimalistic Sultry Midi Dress
Chanel a sultry minimalistic wardrobe for fall in this staple crepe midi dress featuring a sleek sleeveless V-neckline, bungee spaghetti straps, a curve-hugging silhouette, and a front slit accent. Complete the look in low-heeled mules and a chic hat.
Fit & Features
- Sleeveless V-neckline
- Bungee spaghetti straps
- Curve-hugging silhouette
- Front slit accent
- Midi-length hem
- Crepe fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4782
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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She's Got Bold Style Midi Dress
Showcase your fearless bold style in this alluring and chic midi dress! It features a sleeveless one-shoulder neckline with an asymmetrical shoulder strap, a center O-ring cutout, dual waist cutouts, and a midi-length, curve-hugging silhouette with a thigh-high side slit. Complete the look with hoop earrings.
Fit & Features
- Sleeveless one-shoulder neckline
- Asymmetrical single shoulder strap
- Center O-ring cutout
- Dual waist cutouts
- Midi-length hem, bodycon silhouette, high side slit
- Smooth knit fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4774
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Major Obsession Marble Print Midi Dress
The obsession you'll have with this fabulous marble print midi dress is so real! It features a V-neckline with a twist-front design, an alluring front waist cutout to showcase some skin, long fitted sleeves, a ruched side seam that leads to a high-cut side slit, and a midi-length hem with a form-hugging silhouette. The stretchy knit fabric features a trendy marble print pattern. Style this midi dress with spiral heels!
Fit & Features
- V-neckline, twist-front design
- Front waist cutout
- Long fitted sleeves
- Ruched side seam, high side slit
- Midi-length hem, form-hugging fit
- Marble print, stretchy knit fabric
- Runs true to size
Style Number/Barcode: 05102-5309
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Struck By Sultry Halter Mini Dress
Get struck by this sultry halter mini dress sure to capture every eye in the room! The knit dress features a sleeveless halter neck with tie closure, a strappy cutout waist, and a form-hugging silhouette. Complete the look in sassy platform heels.
Fit & Features
- Sleeveless halter neck with tie closure
- Strappy cutout waist
- Form-hugging silhouette
- Mini-length hem
- Lined slinky knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4776
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Swirl Of Splash Crew Mini Dress
A splash of this swirl print mini dress will instantly give your closet a fresh look! The dress features long fitted sleeves, a crew neckline, and a bodycon silhouette on smooth knit fabric with a moderate stretch. Complete the look in a crop denim jacket for a day out with friends!
Fit & Features
- Long fitted sleeves
- Crew neckline
- Bodycon silhouette
- Mini-length hem
- Swirl print
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4779
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Simple Life Crew Tank Midi Dress
All a girl needs is this basic crew tank midi dress perfect for dressing up or down! It features a sleeveless bodice, wide tank shoulder straps, a midi-length hem, and a bodycon silhouette on lined ribbed knit fabric with plenty of stretch. Style this mid-length dress with a jacket and suede booties.
Fit & Features
- Sleeveless crew neckline
- Wide tank shoulder straps
- Midi-length hem
- Bodycon silhouette
- Lined ribbed knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4772
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Links Chain Strap Midi Dress
This stylish midi dress entered the chat! It features a sleeveless V-neckline with trendy chain link shoulder straps, a bodycon silhouette, and a front slit on stretchy, double-lined ribbed knit fabric. Complete the look in clear strap heels.
Fit & Features
- Sleeveless V-neckline
- Chain link shoulder straps
- Bodycon silhouette
- Front slit
- Midi-length hem
- Double-lined, rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4773
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyday Slay Ribbed Knit Midi Dress
Showcase an everyday slay in this curve-hugging midi dress! It features a sleeveless square neckline, spaghetti straps, an open back with a double strap design, a midi-length hem with a bodycon silhouette, and a thigh-high side slit for a sultry accent. The ribbed knit fabric offers plenty of stretch. Style with clear mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Open back, double strap design, tie closure
- Midi-length hem, bodycon silhouette
- High side slit
- Ribbed knit fabric, lining at the bust, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4770
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Beauty Floral Mini Dress
Radiate effortless beauty in this gorg floral mini dress! It features a square neckline, sheer long peasant sleeves to add a chic flair, all-over ruching, a mini-length hem with a form-hugging fit, and an all-over blooming floral print. The sheer chiffon fabric includes a partial knit lining down the body of the dress. Style with dainty duster earrings and a pair of neutral heels.
Fit & Features
- Square neckline
- Sheer long peasant sleeves, elastic cinched hems
- All-over ruching, back zipper, hook and eye closure
- Mini-length hem, form-hugging fit
- Floral print
- Sheer chiffon fabric, partial knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05101-1860
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale