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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Solid Stunner Ruched Tube Dress
We'll keep it brief: this mini is made for for your next night out! Tube-style dress features a curve-hugging cut, strapless neckline, and all-over strategic ruching detail. Don't forget to pair it with the matching duster! Dress slips on and is made from a smooth, solid woven material with moderate stretch.Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05103-0165
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Go With The Flow Maxi Dress
Go with the flow of this gorgeous maxi dress! It features a sleeveless deep V-neckline with a lined crochet lace top, adjustable spaghetti straps, a tie-back detail with a lower back cutout, and a flowy, floor-length skirt with pleated detailing and a relaxed fit. Style this dress with new earrings and strappy sandals for your summer vacay.
Fit & Features
- Sleeveless deep V-neckline
- Lined crochet lace top
- Adjustable spaghetti straps
- Tie-back detail, lower back cutout
- Floor-length skirt, pleated detailing
- Relaxed fit
- Gauze fabric
- Runs true to size
Style Number/Barcode: 05102-0295
Category Name: Casual Dresses
Price: $6.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Breezy Babe Crochet Maxi Dress
Enchant them all in this maxi dress! It's the perf vacay dress you need to pack before that trip!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Lined Crochet Front Design
- Tie Open Back
- Flowy Maxi Length Silhouette
- Textured Knit Fabric I Partial, Mini Length Knit Lining
- Relaxed Fit I Moderate Stretch
Style Number/Barcode: 05102-0294
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plus Thrill Of Knit Ribbed Dress
Toe the perfect line between casually chic and sultry-on-trend in this off-the-shoulder mini. Dress features all-over medium-width ribbing, a scoop neck, decorative wood-like buttons and a full lining. Dress is made from a soft, heavier-weight cotton blend with a fair amount of stretch.
Style Number/Barcode: 15102-0035
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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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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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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Ready For My Snap Midi Dress
Get ready to take all the snaps in this simply stunning midi! The sweater dress features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, double white striped detailing and gold faux snap buttons down each side, and a mid-length fit. The black dress is composed of a ribbed knit fabric with plenty of stretch.Style Number/Barcode: 06005-0096
Category Name: Casual Dresses
Price: $4.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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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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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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Ruffle Ride Skater Dress
Keep it cool in this breezy-beautiful skater dress! It features adjustable spaghetti straps, a seamed V neck bodice, tiers of ruffle trim at the bust, waist, thigh and hem, and an A-line skirt with back zip. Dress is fully lined and made from a lightweight Tencel-blend with natural crinkle-effect and little to no stretch.
Style Number/Barcode: 05102-0329
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Such A Babe Button Down Midi Dress
Yes babe, you'll totally work it in this chic button down midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back, lined and padded cups, flattering horizontal seam detailing along the bust, a hidden back zipper closure, a high rise paper bag waist with a tie front belt, faux button detailing, and a mid-length skirt that offers a form hugging fit. The top is composed of a ribbed linen fabric and the skirt is made from a stretchy knit.
Model is 5'9" with a 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0245
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Smocked Stunner Mini Dress
Showcase the stylish stunner you are in this adorable smocked mini dress! It features a sleeveless bodice, thick smocked shoulder straps with ruffle detailing, a sweetheart neckline, a stretchy and smocked bust, a high waist seam with a ruffle trim, and a flowy skirt with a tiered ruffle hem. The dress is composed of a lightweight woven fabric with a woven skirt lining.
Style Number/Barcode: 05102-0230
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Get Sprung On Florals Mini Dress
Get sprung on this too cute mini dress! It features an off the shoulder neckline with short cuffed sleeves, a trendy tie front with a keyhole cut out, seam detailing, a smocked back, and a short, form hugging fit. The dress is composed of a woven fabric with no stretch.
Style Number/Barcode: 05102-0099
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rainbow Wave Maxi Dress
You love color, so embrace the rainbow! All eyes will be on you in this vibrantly chic maxi dress, which features a multi-hued stripe pattern, spaghetti straps, scoop neck, pockets at either hip, and plenty of stretch. Don't forget to pair it with the matching head wrap!
Style Number/Barcode: 05102-0244
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Trendsetter In Tie Dye Mini Dress
Be a total trendsetter in this fun tie dye mini dress! It features a sleeveless bodice, tank-like shoulder straps, a scoop neckline, a tie front accent, and a short, curve hugging fit. The dress is composed of a stretchy knit fabric.
Style Number/Barcode: 05102-0227
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Not So Basic Mini Dress
Sure, you probably have your share of mini dresses. Now it's time for an of-the-moment upgrade! This ultra-chic mini features an off-the-shoulder elasticized neckline, gathered bodice and sleeves, a back zip, banded waist with back smocking, and pencil skirt with gather-drape detail. Dress is made from a mid-weight woven material with little to no stretch.
Style Number/Barcode: 05101-0165
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral In Love Midi Dress
Fall in love with this romantic floral midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a V neckline created by a knot front detail, a hidden back zipper and hook and eye closure, and an A-line mid-length fit with a front slit. The dress is composed of a lightweight woven fabric.Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0209
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Catch The Bouquet Dress
This neutral ditsy flower pattern dress has us swooning! With a floral bouquet pattern it features a square neckline, ruffled stretchy spaghetti straps, a square back with a hidden zipper and double straight hem down the middle. This mini dressed has a ruched side detailing and an inner linen lining.
Style Number/Barcode: 05102-0207
Category Name: Casual Dresses
Price: $9.97 $47.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Braid For Shade Maxi Dress
Elegantly subdued hues and sophisticated cut lend this maxi its easy appeal. Dress features a halter neck with deep V, banded waist with cutout and two rows of braid trim, a braided clasp back, and an A-line skirt with back zip. Dress is partially lined and made from a soft, crepe-like woven material with little to no stretch.Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0181
Category Name: Casual Dresses
Price: $19.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Life's A Beach Mesh Dress
Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.
Style Number/Barcode: 05102-0159
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Chic Mini Dress
Add some floral chic to your pretty look with this adorable mini dress! It features a sleeveless bodice, tie shoulder spaghetti straps, a sweetheart neckline with a tie front detail, a square back with a hidden zipper and hook and eye closure, a high waist seam, and a flowy A-line skirt. The dress is composed of a woven fabric with a skirt lining, and offers no stretch.
Style Number/Barcode: 05102-0224
Category Name: Casual Dresses
Price: $15.97 $40.90
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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Va Va Venom Knit Dress
You don't bite, but you're ready to pounce! Channel your wild side in this bold mini. Dress slips on, has a curve-hugging fit, and features spaghetti straps and a scoop neck. Dress is made from a ultra-soft brushed knit fabric with a fair amount of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0169
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Life's A Beach Mesh Dress
Hit the pool, bask by the beach, or prep to party in this colorful mesh maxi! Dress features a vibrant tropical print, a strapless neckline, dramatic ruffle trim running from bust to hem, a high front slit, and built-in briefs. Dress bodice is semi-sheer and does not include a top. Maxi is made from a mesh blend material with moderate stretch.
Style Number/Barcode: 05102-0158
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance