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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Heart Of Bloom Ditsy Floral Mini Dress
Go full bloom with a pretty mini dress! The dress features a sleeveless square neckline, a tie-front accent, spaghetti straps, a ditsy floral print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with mules.
Fit & Features
- Sleeveless sweetheart neckline
- Tie-front
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette, form-hugging fit
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-2041
Category Name: Casual Dresses
Price: $18.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Stylish Stunner Ruched Mini Dress
Bring stylish and stunning looks this season in this on-trend mini dress. It features a crew neckline, short sleeves, a front waist cutout with a cross-strap design, ruching, and a mini-length silhouette with ties at the hem. Pair this dress with heeled mules and a chic crossbody purse.
Fit & Features
- Crew neckline
- Short sleeves
- Front waist cutout, cross-strap design
- Ruching
- Short, form-hugging fit
- Ties at the hem
- Ribbed knit fabric
- Runs true to size
Style Number/Barcode: 05102-2029
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cutout Cutie Ruched Mini Dress
Create a chic look with a mini dress that showcases your stunning style! The mini dress features a sleeveless crew neckline, a waist cutout that creates an O-ring design, a ruched drawstring, and a mini-length silhouette. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch.
Fit & Features
- Sleeveless crew neckline
- Waist cutout
- Ruched drawstring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1968
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Total Knockout Knit Midi Dress
Step up in this knockout midi dress that is all the rage! Perfect for stepping out for a casual lunch date or layer this dress for the perfect workwear outfit. The dress features a crew neckline, cap sleeves, and a midi-length silhouette accented with a high side slit. Elevate your look with square toe strappy mules and statement-making earrings!
Fits & Features
- Crew neckline
- Cap sleeves
- Midi length hem
- High side slit
- Ribbed knit fabric
- Plenty of stretch, form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-0897
Category Name: Casual Dresses
Price: $4.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Crew neckline
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Basic Vibes Cutout Maxi Dress
Rock those basic vibes with a maxi dress that keeps its lowkey. The dress features a sleeveless scoop neckline, adjustable spaghetti straps, a sexy lower back cutout, and a maxi-length silhouette. The dress is composed of a lined cotton knit fabric that offers a relaxed fit with a moderate stretch. Complete look with t-strap sandals.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Lower back keyhole
- Maxi length silhouette with a high side slit
- Cotton knit fabric
- Relaxed fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1961
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Free-Spirited Darling Tie-Dye Mini Dress
Channel your boho side with a tie-dye dress that keeps it chic and casual. The dress features a sleeveless V-neckline with a halter neck tie, a tie-dye pattern, an open back with tie-back straps, and a mini-length A-line silhouette with tiered ruffles. The dress is composed of a lined linen fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Halter neck-tie
- Tie-dye pattern
- Open back with tie back straps
- Mini length A-line silhouette
- Ruffles
- Lined linen, relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1952
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Silhouette Ribbed Knit Mini Dress
Create a chic silhouette in this curve-hugging mini dress! It features a wrap front and back design with a V-front and back, long fitted sleeves, a high waist seam, and a mini-length fit. The ribbed knit fabric offers plenty of stretch. Style this dress with cute mules.
Fit & Features
- Wrap front and back, V-front and back
- Long fitted sleeves
- High waist seam
- Short, form-fitting silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 06005-0993
Category Name: Casual Dresses
Price: $6.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Off The Shoulder Ribbed Knit Mini Dress
Button up in a chic mini dress that is perf to dress up or dress down in for your next outing! The dress features an off-the-shoulder neckline, short sleeves, a faux button-down front, and a mini-length silhouette. The dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with mules and denim jacket.
Fit & Features
- Off the shoulder neckline
- Short sleeves
- Faux button down front
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1911
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Charm Sleeveless Mini Dress
Bring the floral charm with a pretty mini dress! The dress features a sleeveless square neckline, smocked tie-shoulder straps, a floral print, and a mini-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with sandals.
Fit & Features
- Sleeveless square neckline
- Smocked tie-shoulder straps
- Floral print
- Mini length silhouette
- Lightweight woven fabric, knit lining
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-1905
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Pep It Up Plaid Mini Dress
Pep it up in a cute plaid mini dress! The dress features a sleeveless square neckline, spaghetti straps, a plaid print, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Mini-length silhouette
- Knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1866
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Such A Charmer Ditsy Floral Mini Dress
Charm them all with a mini dress that makes a sweet impression! The dress features a sleeveless square neckline, spaghetti straps, a ditsy floral print, 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 mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ditsy floral print
- Mini-length silhouette
- Ribbed knit fabric, knit lining
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1895
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Chic Ribbed Knit Mini Dress
Make a chic impression with a mini dress that gives off those effortlessly chic vibes! The dress features a sleeveless collared neckline, a button-down front, contrasting hued trim, 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 clear mules.
Fit & Features
- Sleeveless collared neckline
- Button-down front
- Contrasting hued trim
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-0990
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Perfect Match Ponte Knit Skater Mini Dress
This mini dress and you are a perfect match, babe! The dress features a sleeveless square neckline, spaghetti straps, tie-back straps, a lower back keyhole, and a pleated tennis-style styled skater skirt. The dress is composed of a lined Ponte knit that offers a form-hugging fit with a moderate stretch. Complete look with wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Tie-back straps, lower back keyhole
- Pleated tennis skirt, skater silhouette
- Lined Ponte knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1863
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Style Plaid Mini Dress
Showcase a chic and perfect style in this plaid mini dress that is a must-have for fall. It features a sleeveless square neckline, spaghetti straps, and a short, curve-hugging fit. Complete the outfit with a faux leather jacket to add an edgy vibe to the look.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-fitting silhouette
- Knit fabric, moderate stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 05102-1864
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Romance Asymmetrical Mini Dress
Fall in love with this dreamy tropical printed mini dress that is a must-have for summer vacays. It features a sleeveless V-neckline, adjustable spaghetti straps, side ruched detailing, and a mini-length, curve-hugging silhouette with a trendy asymmetrical hem. Style this dress with cute mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Side ruched detailing
- Short, form-hugging fit
- Asymmetrical hem
- Brushed knit fabric, plenty of stretch, tropical palm leaf print
- Runs true to size
Style Number/Barcode: 05102-1857
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Stunner Asymmetrical Midi Dress
This dress will have you looking stunning as you watch the sunset on your next vacay! It features a sleeveless V-neckline, adjustable spaghetti straps, a beautiful tropical floral print, and a mid-length, curve-hugging silhouette with an asymmetrical hem. Style this dress with hoop earrings and strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Back cross-back design
- Ruched detailing
- Mid-length, form-hugging fit, asymmetrical hem
- Knit fabric, moderate stretch, tropical floral print
- Runs true to size
Style Number/Barcode: 05102-1860
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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So Adored Cut Out Mini Dress
Feel so beloved in this pretty mini dress! The dress features a scoop neckline, short sleeves, a midriff cutoff with tie waist accent, and a mini-length silhouette. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with platform heels.
Fit & Features
- Scoop neckline
- Short sleeves
- Midriff cutout, tie waist accent
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-1859
Category Name: Casual Dresses
Price: $19.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty Vibes Butterfly Printed Mini Dress
Showcase those sweet and flirty vibes in this trendy knit mini dress. It features spaghetti straps, a square neckline, ruching down the sides, ties at the hem, and a short, form-hugging silhouette. The lightweight ribbed knit fabric has an adorable colorful butterfly print, making it a perf dress for the spring season. Complete your look with a denim jacket and strappy sandals.
Fit & Features
- Spaghetti straps
- Square neckline
- Ruched detailing and ties at the hem
- Mini-length, curve-hugging fit
- Unlined ribbed knit fabric
- Plenty of stretch
- Colorful butterfly print
Style Number/Barcode: 05102-1705
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Tropics Babe High Slit Midi Dress
Hit the tropics in this gorge midi dress! The dress features a sleeveless V-neckline, spaghetti straps that cross at the back, a tropical print, a ruched side seam, and a midi-length silhouette with a high side slit. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a floppy hat and sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross at the back
- Tropical print
- Ruched side seam
- Midi length silhouette, high side slit
- Smooth knit fabric
- Form hugging fit, runs true to size
Style Number/Barcode: 05102-1799
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfectly Plaid Knit Mini Dress
You'll look perfectly stylish in this plaid mini dress that you can take from day to night! It features a sleeveless square neckline, spaghetti straps, and a short, form-fitting silhouette that will hug your curves. Style with sneakers for a casual daytime look, and layer on a faux leather jacket and style with ankle booties for night.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Mini-length, form-hugging fit
- Lined knit fabric, moderate stretch
- Plaid print
- Runs true to size
Style Number/Barcode: 05102-1687
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Preppy And Trendy Plaid Ruched Mini Dress
Keep it preppy in a plaid mini dress that is perf for your next brunch with the squad! The dress features a plaid print, a sleeveless square neckline, spaghetti straps, dual ruched drawstrings, and a mini-length silhouette. Complete look with mules and a jelly purse.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Dual ruched drawstrings
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-1679
Category Name: Casual Dresses
Price: $19.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Fab Tie Dye Midi Dress
Keep it totally fab with a midi dress that channels those pretty vibes! The dress features a sleeveless V-neckline, spaghetti straps, a tie-dye print, and a midi silhouette with a high side slit. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Tie-dye print
- Midi silhouette
- High side slit
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1633
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Splash Of Style Tie Dye Midi Dress
Add a splash of style with a pretty midi dress! The dress features a sleeveless cowl neckline, spaghetti straps, a strappy back design, a tie-dye print, and a midi-length silhouette. The dress is composed of a lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with clear mules.
Fit & Features
- Sleeveless cowl neckline
- Spaghetti straps
- Strappy back design
- Tie-dye print
- Midi length silhouette
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-1659
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Vibes Tie-Dye Knit Mini Dress
Bring the casual vibes this season with this trendy tie-dye knit mini dress. It features a crew neckline, short sleeves, side ruching, and a mini-length, curve-hugging silhouette with side ties at the hem. Complete the look with cute sneakers for the perf everyday outfit.
Fit & Features
- Crew neckline
- Short sleeves
- Side ruching
- Side ties at the hem
- Short, form-hugging fit
- Knit fabric, tie-dye print
- Runs true to size
Style Number/Barcode: 05102-1588
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free