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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Ruche Hour Sleeveless Mini Dress
Subtly sophisticated, this ruched mini is equally sultry—and ready for evenings out! Dress features a mesh overlay, high neck, slim-cut sleeveless bodice, and ruching detail at the sides, back, and front beginning at the waist. Slip-on style is fully lined and made offers a fair amount of stretch.
Style Number/Barcode: 05103-0073
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Read My Lips Tunic Top
Make a strong style statement without saying a word in this tunic top. Pair it with skinny denim or go bold and make it a mini! Top features spaghetti straps and a large rainbow-colored graphic. Top nips slightly at waist and is made from an ultra-soft woven material with a fair amount of stretch.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06002-0131
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sweetly Tied Skater Dress
Sweeten up your look with this adorable red skater dress! It features a sleeveless bodice, adjustable halter straps that lead to a button back closure with a keyhole cut out below, a back zipper and hook and eye closure, a V neckline, a cute tie front detail, and a flowy skater skirt. The dress is composed of a lightweight linen fabric with a short knit lining.
Style Number/Barcode: 05102-3826
Category Name: Casual Dresses
Price: $13.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Love Bud Sweetheart Dress
Hey sweetheart, Hey love bud , Hey little cutie ! The dress features a sweetheart neckline , tie yourself ribbon spaghetti straps, and a built in wire for a bra-like effect. The back-line of this dress is square and includes a hidden zipper. The bodice of this dress is a body con style that is form fitting and shows off those curves and has a mini slit at the hem. The dress is composed of a canvas material that offers moderate stretch. Muah!
Style Number/Barcode: 05102-0219
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Breezy Like Me Sleeveless Ruffled Maxi Dress
An effortless woven maxi dress for shower celebrations, graduations, or meet-ups with the girls! It boasts a flowy ruffled silhouette and a floor-length hem perfect for styling with cute sandals.
Fit & Features
- Cotton fabric, woven lining
- Square neckline
- Adjustable spaghetti straps
- Flowy ruffled silhouette
- Maxi-length floor hem
- Runs true to size
Style Number/Barcode: 05102-6022
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Sweet As Pie Skater Dress
Honey you will look sweet as pie in this cute skater dress! This piece features a V neckline, spaghetti straps, a skater style skirt, and the best part...It has pockets! This dress is comprised of a soft crepe material that offers moderate stretch.Style Number/Barcode: 05101-8838
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Anything But Basic Maxi Dress
This sophisticated, streamlined maxi will more than earn its place in your closet this season. Chic and versatile, it goes pretty much anywhere you do! Dress features a square neckline, all-over rib knit detail, crisscross spaghetti straps, adjustable keyhole tie detail, back cutout, and side slit. Dress is partially lined and made from a soft, densely knit material with moderate stretch.
Style Number/Barcode: 05102-0012
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Make It Snappy Dress
Time to flaunt those curves and make it snappy girl! This white toned dress features adjustable spaghetti straps that lead to a square back. The dress has a form fitting silhouette and an a-symmetrical hem at the hip with a gold button detail and a small slit. This ensemble is composed of a ribbed knit material that offers moderate stretch.Style Number/Barcode: 06005-0129
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Fab And Flared Midi Dress
Keep it fab in this twirl-worthy must have! The black dress features a V neckline, spaghetti straps and a midi length silhouette with flared hem. Dress is composed of an unlined ribbed sweater knit fabric that offers a form hugging fit with a moderate stretch.Style Number/Barcode: 06005-0113
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Buckled In Sleeveless Mini Dress
Ready to take this sultry mini for a ride? We thought so! Dress features all-over ribbing and a sleeveless bodice with scoop neck and buckle-detailed shoulder straps. Dress is made from a soft, densely woven material with plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-0112
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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See You Soon Shirt Dress
A classic with a twist—quite literally! This ultra-chic little white shirt dress is beyond versatile: think work, weekend, lunch, brunch, and everything in between! Dress features a collared open V front, a seamed back, long sleeves with double-button cuffs, flattering twist detail at waist, and a draped straight-line skirt.Style Number/Barcode: 06003-0310
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Oh Snap Button Midi Dress
Be all over everyone's snaps in this midi dress! It has a scoop neckline, tank-style straps, and a row of faux snap buttons down the side of the skirt that leads to a side slit. Sweater dress has a comfortable slim fit and is composed of a ribbed knit fabric with plenty of stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6308
Category Name: Casual Dresses
Price: $39.90
Availability: Out of Stock
Product Badge:- Clearance
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Plus From The Block Midi Dress
Where you from Lil' Mama? This cute dress has a flattering V neckline paired with thin straps and a sexy, bodycon fit with a small back slit. The garment is composed of a crepe fabric that offers a moderate stretch and is detailed with a multi-color block design.Model is 5'9" with a 44" bust, 37" waist and 47" hips. She is wearing a size 1X
Style Number/Barcode: 15102-0028
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Basic Essentials Midi Dress
Sometimes less is more! This basic red midi dress can be kept casual or paired with accessories to dress it up! Throw on your favorite sunnies or wide brimmed hat to achieve beach worthy vibes! This dress features a scoop neckline, narrow shoulder straps and a soft to the touch fabric feel creating a curve hugging fit with plenty of stretch.
Style Number/Barcode: 15102-0020
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Floral Fiesta Maxi Dress
This beautiful floral maxi dress is perfect for your spring and summer occasions! It features a stretchy off the shoulder neckline with a ruffle pop over, a stretchy high waist seam, and a flowy floor-length skirt. Dress is composed of an unlined crepe fabric with no stretch.Model is 5'8 with a 42" bust, 35" waist, and 45" hips. She is wearing a size 1X.
Style Number/Barcode: 15102-0033
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Strappy & Stunning Mini Dress
This must-have dress is stylin' and so fab! The mustard yellow asymmetrical dress features a deep V neckline, spaghetti straps, a wrap bodice with ruching on the side, and a wrap skirt with an asymmetrical hem. Dress is composed of an unlined crepe fabric with a moderate stretch.
Style Number/Barcode: 15103-0025
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Too Hot to Handle Halter Knit Mini Dress
This halter mini dress hugs you with a bodycon fit and a side sash that brings the drama and accentuates your curves. Pair with sandals for brunch by the beach or vacay!
Fit & Features
- Texture knit stretchy fabric, stretchy knit lining
- Halter neckline with hardware trim, spaghetti strap tie
- Padded bra cups
- Back zipper and hook-eye closure
- Bodycon silhouette
- Front wrap sash design
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000115
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Strings Attached Sweater Mini Dress
Get all tied up with this LBD. It features spaghetti straps that lead to a sexy lace-up back, a sweater knit, and a mini length. Dress offers plenty of curve hugging stretch!Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-6358
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sleek Style Ribbed Midi Dress
Keep it sleek and stylin' with this yellow ribbed midi dress! It features a deep round neckline, spaghetti straps, and a traditional midi length. Ribbed knit offers plenty of curve hugging stretch.Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6284
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
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Crochet Babe Tunic
All you need is sand and sun with this peach crochet tunic! It has a deep V neckline, lined cups, adjustable shoulder straps leading to a low square back, an exposed silver zipper closure, and a comfortable slim fit.Tunic is composed of an unlined crochet fabric with minimal stretch.Model is 5'7 with a 34" bust, 24" waist, and 36" hips. She is wearing a size small.
Style Number/Barcode: 06005-6289
Category Name: Casual Dresses
Price: $5.00 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Take A Snap Button Midi Dress
You'll want to take tons of snaps for the gram in this button down midi dress! It features a sleeveless bodice, tank-like shoulder straps, gold faux snap buttons, a front slit, and a midi length. The black dress is composed of a ribbed knit fabric with plenty of stretch.Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.
Style Number/Barcode: 06005-6300
Category Name: Casual Dresses
Price: $36.90
Availability: Out of Stock
Product Badge:- Clearance
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Fit On Point Sweater Dress
Make your entire 'fit on point with this adorable sweater dress! It features an off the shoulder elastic banded neckline, long fitted sleeves, a narrow belt around the waist with a small gold buckle and gold grommets, and a form hugging fit. The mauve dress is composed of a ribbed knit fabric with plenty of stretch.
Style Number/Barcode: 06005-6214
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Zipped With Style Knit Dress
Zip your look with style with this trendy knit dress! It features a mini mock neck, long fitted sleeves, a complete zip font with a chic O ring detail, and a belted tie waist. The burgundy dress is composed of a ribbed knit fabric that offers plenty of stretch and a curve hugging fit.
Style Number/Barcode: 06005-6152
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Stripe It Right Sweater Dress
Stripe it right with this adorable sweater dress! It features a mini mock neck, short cap sleeves, and a short, curve hugging fit. The white dress is composed of a ribbed knit fabric that offers plenty of stretch and showcases a black and red striped print.
Style Number/Barcode: 06005-6179
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance