Casual Dresses
Casual dresses that keep up with your plans—brunch, outdoor concerts, coffee runs, and everything in between. From easy ribbed knits to breezy jersey and mesh, these pieces prove laid-back can still look styled. Make it flirty with a ruffled dress or bodycon mini, or keep it flowy with midi and maxi silhouettes. Mesh details add a little edge, while sleeveless minis and long-sleeve staples cover every season. Whether you’re layering up for a chill weekend or slipping into something light for a last-minute dinner date, these casual dresses are made to move with your mood—and 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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Steal The Spotlight Leopard Slit Midi Dress
Steal the spotlight looking so fierce in this leopard midi dress! It features a sleeveless V-neckline, spaghetti straps, a flowy midi-length hem, and a front slit perfect for showing off some skin. Style with a pair of strappy sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length hem, flowy silhouette
- Front slit
- Leopard print
- Crepe knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4306
Category Name: Casual Dresses
Price: $19.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual-Chic Moment Mini Dress
Have a stylish casual-chic moment in this ribbed knit mini dress. It features a crew neckline, long fitted sleeves, a trendy wrap tie-front design, and a short, form-hugging silhouette. Complete the look with heeled booties.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Wrap tie-front design
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4298
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Classic Chic Shirt Dress
This classic chic mini shirt dress is everything you need and more. It features a collar, a plunging V neckline with lace-up ties, long sleeves with buttons to cuff, a high waist seam, and a mini-length silhouette. The dress is composed of a woven fabric with no stretch. Complete look with thigh-high boots and a cabby hat.
Fit & Features
- Collar, V-neckline
- Lace-up front
- Long sleeves, buttoned cuffs
- High waist seam
- Mini length silhouette
- Woven fabric
- Form hugging fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1464
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sporty Babe Hooded Mini Dress
Achieve that trendy sporty babe look with this casual ribbed knit mini dress. It features a hoodie, a high neckline with front drawstrings, long sleeves, ruched side detailing, and a short, curve-hugging silhouette. Style this dress with cute sneakers.
Fit & Features
- Hoodie
- High neckline, front adjustable drawstrings
- Long fitted sleeves
- Ruched sides, adjustable drawstrings
- Mini-length, form-fitting silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4324
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Embrace The Chill Mock Neck Sweater Tunic
Embrace the chill in style! This sweater tunic features a sleeveless, mock neck design on a form-fitting silhouette and mini-length hem. Composed of a soft eyelash knit fabric with a moderate stretch. Complete the look in an oversized blazer.
Fit & Features
- Sleeveless, mock neck
- Form-fitting silhouette
- Mini-length hem
- Soft eyelash knit fabric
- Moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1113
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Born to Be Bold Lace Leopard Maxi Dress
This curve-hugging maxi brings the heat with sultry lace, sheer mesh, and sky-high slits—made for nights when playing it safe isn't on the mood board!
Fit & Features
- Leopard print, mesh fabric, stretchy knit lining
- Lace sweetheart neckline, lace bust, lace shoulder straps
- High side slits
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000265
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wild At Heart Brushed Knit Leopard Mini Dress
Showcase your wild side in a mini dress that makes a fierce impression! The dress features a leopard print, a crew neckline, long sleeves, ruched drawstrings, and a mini-length silhouette with a rounded hem. The dress is composed of a brushed knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto and ankle booties.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched drawstrings
- Leopard print
- Mini length silhouette
- Brushed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4263
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Everyday Plaid Mini Dress
Create an elevated everyday outfit with this chic plaid mini dress! It features an on-trend square neckline, long sleeves, and a short, form-hugging fit. Style this dress with an oversized faux leather blazer and ankle booties.
Fit & Features
- Square neckline
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Plaid print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4228
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Chic Twist Long Sleeve Midi Dress
The twist back on this midi dress is pretty chic! It features long sleeves, a crew neckline, and a form-fitting silhouette. The dress is composed of a ribbed knit fabric with a moderate stretch. Perfect for styling with suede booties and a statement bracelet.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Twisted open back detail
- Midi-length hem
- Form-fitting silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1075
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Moves Ruched Mini Dress
Make chic moves in this curve-hugging mini dress! It features a trendy mock neckline, long sleeves, a sultry cutout above the bust, ruched detailing down the sides, and a short, form-fitting silhouette. Style this dress with sleek hoop earrings.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Cutout above the bust
- Ruching down the sides
- Mini-length, form-fitting silhouette
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4144
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fiercely Bold Dragon Graphic Mini Dress
Keep it fiercely bold with a mini dress that slays! The dress features a V-neckline, slashed detailing, an image of a dragon, text that reads: "Free Soul", long sleeves, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with a moto jacket and booties.
Fit & Features
- V-neckline
- Slashed distressing
- Image of dragon
- "Free Soul" in black text
- Long sleeves
- Mini length silhouette
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1048
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Totally Tie-Dye Mock Neck Dress
You'll tie-dye for this mock neck dress featuring long sleeves and a mini-length hem. The dress is composed of a ribbed knit fabric with a moderate stretch. Style with edgy booties.
Fit & Features
- Long fitted sleeves
- Mock neckline
- Tie-dye pattern
- Bodycon silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4206
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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Back To Basics Turtleneck Mini Dress
Your head-to-toe look needs this turtleneck dress as a base for creating fab looks! It features fitted long sleeves and a short-length hem. This dress is composed of crepe-lined fabric with a moderate stretch. Style with a duster coat.
Fit & Features
- Fitted long sleeves
- Turtleneck design
- Bodycon silhouette
- Short-length hem
- Crepe-lined knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4299
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rocker Babe Slashed Mini Dress
Rock on babe in a tee that shows off your edgy side! The mini dress features a crew neckline, short sleeves, a bold rock-inspired graphic, a slashed design at the back, and a mini-length silhouette. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with combat boots and a swag chain belt.
Fit & Features
- Crew neckline
- Short sleeves
- Rock-inspired graphic
- Slashed design at back
- Mini length silhouette
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1027
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic Basic Mock Neck Mini Dress
This mini dress is the perfect day-to-night style! It features long sleeves, a mock neckline, and a bodycon silhouette designed to accentuate your curves. Complete the look with a necklace.
Fit & Features
- Long fitted sleeves
- Mock neckline
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-4281
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Shirr Thing Long Sleeve Mini Dress
This mini dress is sure to be a hit for your closet! It features long fitted sleeves, a mock neck, and a side shirring detail that shapes the high-low short hem. The brushed knit fabric offers a moderate stretch. Style with an oversized jacket.
Fit & Features
- Long sleeves
- Mock neck
- Side shirring detail
- Bodycon silhouette
- High-low mini hem
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4139
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Daring Chic Cutout Mini Dress
Dare to go bold with a dress that is anything but basic! The dress features a collared neckline, a multi-button down front, long sleeves, dual waist cutouts, 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 heels and a crossbody.Fit & Features
- Collared neckline
- Multi-button down front
- Long sleeves
- Dual waist cutouts
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4276
Category Name: Casual Dresses
Price: $5.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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A Casual Slay Ruched Midi Dress
You'll casually slay in this basic chic midi dress with elevated details. It features a mock neckline, long fitted sleeves, a curve-hugging silhouette, and a front slit with ruching. Style this dress with trendy clear mules.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Form-fitting silhouette
- Front slit, ruching
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4284
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
- Mock neckline
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All Eyes On You High Slit Maxi Dress
Giving "I didn’t come to play, I came to slay" energy. With a draped neckline, leggy side slit, and flattering ruching—this dress is a total scene-stealer from cocktail hour to afterparty.
Fit & Features
- Soft knit fabric with stretch, full knit lining
- Draped cowl neckline with adjustable spaghetti straps
- Side slit
- Form-hugging fit
- Maxi-length hem
- Runs true to size
Style Number/Barcode: 05102-000059
Category Name: Casual Dresses
Price: $19.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Totally Fab Ribbed Mini Dress
Keep your look totally fab in a mini dress that keeps it effortlessly chic! The dress features a sleeveless V-neckline, bungee spaghetti straps, 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 V-neckline
- Bungee spaghetti straps
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06002-1050
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Simply Sultry And Stunning Mini Dress
You'll look simply sultry and stunning in this lightweight knit mini dress! It features a strappy cross-front design with a V-neckline, long fitted sleeves, an open back with a strappy cross-back design, and a short, curve-hugging fit. Style this dress with clear mules.
Fit & Features
- Front and back cross-strap designs
- V-neckline
- Open back
- Long fitted sleeves
- Mini-length, form-fitting silhouette
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4289
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Basic Ribbed Knit High Slit Midi Dress
Channel effortless style while looking chic in a knit dress! The dress features a mock neck, long sleeves, an asymmetrical high side slit, and a midi-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete the look with ankle booties and a moto jacket.
Fit & Features
- Mock neck
- Long fitted sleeves
- Asymmetrical high side slit
- Midi-length silhouette
- Ribbed knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 06005-1174
Category Name: Casual Dresses
Price: $16.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Drawn To Glam Ruched Mini Dress
Get drawn to this fab dress that creates a head-turning moment. The dress features a mock neck, long sleeves, 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. Complete look with mules and dainty rings.
Fit & Features
- Mock neck
- Long fitted sleeves
- Ruched drawstring
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4230
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale