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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Sharp Lines Asymmetrical Long Sleeve Midi Dress
Strike a fierce impression in a ribbed knit dress with an asymmetrical off-the-shoulder neckline, a pleated popover accent, fitted long sleeves, and a midi-length hem. Complete the look with strappy heels for the perfect work-to-happy hour look!
Fit & Features
- Ribbed knit fabrication
- Asymmetrical off-the-shoulder neckline
- Pleated popover accent at the neckline
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5947
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Luxe Charm Cashmere Knit Hanky Hem Mini Dress
Channel a luxe aura in a ribbed cashmere-like knit dress that features a boat neckline, long fitted sleeves, a partially open back design, and a short hanky hem with an A-line silhouette. Complete the look with knee-high boots and leg warmers for a chic moment!
Fit & Features
- Ribbed cashmere-like knit fabrication, moderate stretch
- Boat neckline
- Long fitted sleeves
- Partial open back, tie-back spaghetti straps
- Mini-length hanky hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-6053
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Vibes Long Sleeve Ruched Midi Dress
Channel sleek vibes in a midi dress that features a boat neckline, fitted long sleeves with thumb holes, and ruching that enhances curves. Complete look with strappy heels to take you from the office to happy hour!
Fit & Features
- Smooth knit fabrication, double-lined
- Boat neckline
- Long sleeves with thumb holes
- Ruching
- Midi length hem
- Runs true to size
Style Number/Barcode: 05101-3954
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casual Glam Ribbed Knit Long Sleeve Mini Dress
The ribbed knit dress features a mock neck, long sleeves accented with thumb holes, and a mini-length hem. For a casually glam vibe, complete the look with ankle booties.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Mock neckline
- Long fitted sleeves with thumb hole accents
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-6014
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Button-Down Drop Waist Mini Dress
So elevated, this adorable mini dress is designed with a textured knit fabric and a sleek button-down front. It features a sleeveless square neckline with tank straps, a drop waist, and a short pleated A-line silhouette for that cute flair.
Fit & Features
- Textured knit fabric, sewn-in knit lining
- Square neckline
- Tank shoulder straps
- Button-down front
- Drop waist
- Mini-length pleated A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3842
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sleek Vibes Off The Shoulder Knit Midi Dress
Keep it sleek and stylish in a ribbed knit dress that features a v-neckline that can be worn off-the-shoulder, fitted long sleeves, and a midi-length hem. Complete the look with sneakers to add a casual touch!
Fit & Features
- Lined ribbed knit fabrication
- V-neckline and off-the-shoulder
- Long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5942
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Adorable Stunner Strapless A-Line Mini Dress
You'll be an adorable stunner in this mini dress designed with crepe fabric with a contrast color block outline for a chic look. It features a strapless straight-across neckline, a high waist seam, and a short A-line silhouette to add that flirty flair.
Fit & Features
- Crepe fabric, stretchy knit lining
- Contrast color block outline
- Strapless straight neckline
- High waist seam
- Back zipper closure
- Mini-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05101-3801
Category Name: Casual Dresses
Price: $14.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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All Things Cozy High Slit Knit Midi Dress
Oh-so-cute and cozy, this knit midi dress is a seasonal staple. It features a mock neckline, long fitted sleeves, an asymmetric mid-length hem creating a thigh-high side slit, and a form-hugging silhouette. The ribbed hacci knit fabric has an ultra-soft feel with plenty of stretch. Style this midi dress with knee-high boots for a latte date.
Fit & Features
- Mock neckline
- Long fitted sleeves
- Asymmetric mid-length hem
- Thigh-high side slit
- Form-hugging fit
- Ribbed hacci knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-5333
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect Curves Ribbed Knit Off-The-Shoulder Midi Dress
Showcase your perfect curves in this midi dress designed with soft ribbed knit fabric. It features an off-the-shoulder neckline with a chic fold-over design, long fitted sleeves, and a midi-length bodycon silhouette.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Midi-length bodycon fit
- Runs true to size
Style Number/Barcode: 05102-5894
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Perfection Long Sleeve Knit Mini Dress
This ribbed knit mini dress will create perfect casual 'fits! It features a square neckline, long fitted bell sleeves with cute flared-out hems, and a mini-length, form-hugging silhouette. The lined knit fabric offers plenty of stretch for comfortable wear. Style with knee-high boots.
Fit & Features
- Ribbed knit fabric, knit lining, plenty of stretch
- Square neckline
- Long fitted bell sleeves, flared hems
- Form-hugging fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-5889
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Seasonal Staple Ribbed Knit Bell Sleeve Mini Dress
This adorable ribbed knit mini dress will be your fave staple of the season featuring a square neckline, long bell sleeves, and a short form-hugging silhouette. Style with knee-high boots for a casual party.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Square neckline
- Long bell sleeves
- Mini-length bodycon fit
- Runs true to size
Style Number/Barcode: 06005-2086
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Like Me Scoop Neck Skater Mini Dress
Showcase your sweet side in this ribbed knit mini dress made to please the crowd! It features a sleek scoop neckline and a skater silhouette that flatters every figure. Style with a handbag.
Fit & Features
- Stretchy ribbed knit fabric
- Scoop neckline
- Tank shoulder straps
- Skater silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 06005-000006
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Stylish Embrace Cable Knit Midi Dress
Embrace a cozy vibe in a cable knit dress that features a trendy v-neckline, fitted long sleeves, and a midi-length hem. Complete look with ankle booties!
Fit & Features
- Unlined cable knit fabrication
- V-neckline
- Fitted long sleeves
- Midi length hem
- Runs true to size
Style Number/Barcode: 06005-2097
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Layered In Glam Ribbed Knit Long Sleeve Maxi Dress
Nail that layered look in a ribbed knit dress featuring a plunging square neckline, a bralette inset with lace trim, fitted long sleeves, and a maxi-length hem with a back slit accent. Complete the look with trendy ankle booties for the ultimate vibe.
Fit & Features
- Ribbed knit fabrication, plenty of stretch
- Square neckline
- Bralette inset with lace trim
- Fitted long sleeves
- Long hem length
- Back slit
- Runs true to size
Style Number/Barcode: 05102-5848
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Mesmerizing Glam Abstract Ruched Midi Dress
Step out and mesmerize in a midi dress that features a sleeveless square neckline, ruching throughout to enhance curves, and an abstract marble print. Complete look with strappy heels for a look that's ready for date night!
Fit & Features
- Lined mesh fabrication
- Sleeveless square neckline
- Ruching
- Abstract marble print
- Midi length hem
- Runs true to size
Style Number/Barcode: 05102-5937
Category Name: Casual Dresses
Price: $19.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Game Plunge V-Neck Bubble Skater Dress
Win hearts in this adoring bubble skater dress perfect for dressy occasions! Boasting a flattering skater silhouette, this poplin woven dress is designed with a plunge V-neckline and back to show some skin, short ruffled bubble sleeves, and a bubble short-length hem. Complete the look in strappy sandals.
Fit & Features
- Poplin woven fabric, sewn-in knit lining
- Plunge V-Neckline
- Short ruffled bubble sleeves
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-2935
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Social Butterfly Square Neck Floral Mini Dress
A dreamy butterfly floral mini dress perfect for social girlies! The mini-length dress features a square neckline that showcases a ribbon trim for romance, adjustable spaghetti straps to get a perfect fit, front metal closures, and a form-hugging silhouette that will flatter your figure. Complete the look in lace-up stiletto heels and a purse for a date!
Fit & Features
- Woven fabric lined with stretchy knit
- Butterfly floral print
- Adjustable spaghetti straps
- Ribbon trim, front metal closures
- Back zipper and hook-eye closure
- Form-hugging silhouette
- Runs true to size
Style Number/Barcode: 05102-5623
Category Name: Casual Dresses
Price: $5.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Leopard Print Woven A-Line Midi Dress
Trendy and elevated, this leopard-printed woven midi dress features a sleeveless square neckline, adjustable spaghetti straps for a customized fit, and a partially smocked back for added stretch. The high front slit adds a bold vibe to the mid-length A-line silhouette.
Fit & Features
- Leopard-printed woven fabric, no stretch
- Square neckline, underbust seam
- Adjustable spaghetti straps
- Partially smocked back design
- High front slit
- Midi-length A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-5923
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Polished Perfection Vest Pleated Short Dress
Capture polished perfection in this chic vest pleated short dress! Designed with a structured twill woven fabric, this dress features a fitted vest top with an A-line skirt. The top is shaped with a sleeveless V-neckline and tank shoulder straps, followed by a button-front design and an angled cropped hem for a snatched look. The chic waist cutout adds a touch of allure, leading to a fitted high waist and a flowy, pleated short-length hem. The dress includes a back zipper closure for effortless styling. Complete your look with gold hoops and strappy mules!
Fit & Features
- Non-stretch twill woven fabric
- Sleeveless V-neckline with tank shoulder straps
- Button-front design, angled cropped hem
- Back zipper with hook and eye closure
- Waist cutout, high-rise skirt with pleating
- A-line fit
- Runs true to size
Style Number/Barcode: 05102-5536
Category Name: Casual Dresses
Price: $5.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twist Of Chic High-Slit Knit Midi Dress
Bring a twist of chic to the every day with a midi dress that features an asymmetrical one-shoulder neckline with a trendy twist shoulder accent and a daringly high side slit. Complete look with slingback shoes to take you from the office to happy hour!
Fit & Features
- Stretchy knit fabrication
- Asymmetrical one-shoulder neckline
- Twist shoulder strap accent
- High side slit
- Midi-length hem
- Bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5983
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On The Down Low Denim Strapless Midi Dress
Take your look on the down low in this denim midi dress! The knee-length dress features a strapless neckline, stretchy smocked back, and button-down front closures, this bodycon dress will have you breaking the fashion barriers. With belt loop accents, three-pocket styling, and a midi-length hem, this denim stunner gives you the power to take risks and turn heads! Style this midi dress with a purse and block heels for a birthday brunch!
Fit & Features
- Strapless neckline
- Stretchy smocked back
- Button-down front closures
- Bodycon silhouette, midi-length hem
- Belt loop accents, three-pocket styling
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-5283
Category Name: Casual Dresses
Price: $5.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic Choice Knit Off-The-Shoulder Maxi Dress
This trendy ribbed knit maxi dress is a chic choice for the season offering plenty of stretch for comfortable wear. It features an off-the-shoulder fold-over neckline, long fitted sleeves, and a maxi-length bodycon silhouette accented with a back slit.
Fit & Features
- Ribbed knit fabric with plenty of stretch
- Off-the-shoulder neckline, fold-over design
- Long fitted sleeves
- Back slit
- Maxi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 06005-2104
Category Name: Casual Dresses
Price: $6.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Girl Power Leopard Print Strapless Midi Dress
Show off major girl power in this sexy leopard print midi dress that was made for all eyes on you. It features a strapless straight-across neckline, ruching down the side seams, a midi-length hem, and a bodycon silhouette to put your gorgeous figure on display. The lined sheer mesh fabric features an all-over leopard print pattern to amp up the look. Style this midi dress with strappy stilettos for a nightclub!
Fit & Features
- Strapless straight-across neckline, no-slip strip
- Ruched side seams, hidden side zipper, hook and eye closure
- Midi-length hem
- Bodycon silhouette
- Leopard print
- Sheer mesh fabric, mini-length knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05101-3211
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Serving Sleek Square Neck Bodycon Midi Dress
Serve a gorgeous sleek silhouette in this brushed knit midi dress featuring a sleeveless square neckline, thin tank straps, and a midi-length bodycon fit to hug your curves. Style with hoop earrings and stiletto heels.
Fit & Features
- Brushed knit fabric with knit lining, plenty of stretch
- Square neckline
- Thin tank shoulder straps
- Midi-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-5975
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale