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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Major Flirt Ruffle Hem Mini Dress
You'll be a major flirt in this absolutely adorable ruffle hem mini! The dress is perf paired with some wedges for a spring day out!
Fit & Features
- Short sleeves
- Wrap front | V neckline
- High rise elastic banded waist
- Wrap front skirt | Ruched detailing
- Ruffle hem
- Stretchy knit fabric
Style Number/Barcode: 05102-0651
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty Palm Ruched Maxi Dress
Keep it pretty underneath the palm trees in a maxi dress that will have you vacay-ready! The dress features a sleeveless square neckline, adjustable spaghetti straps, a pretty tropical palm leaf print, a high ruched side slit, and a maxi length silhouette. The dress is composed of a smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals.
Fit & Features
- Sleeveless square neckline
- Adjustable spaghetti straps
- Tropical palm leaf print
- High ruched side slit
- Maxi length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0639
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Little Bit Of Drama Puff Sleeve Mini Dress
A streamlined LBD with a little bit of drama. Adds some strappy heels and gold-tone jewelry for an eyecatching look!
Fits & Features
- Square Neckline
- Sheer Dobby Mesh Puff Short Sleeves
- Mini Length Silhouette
- Crepe Fabric
- Form Hugging Fit I Moderate Stretch
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0734
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Off The Shoulder Button Front Midi Dress
The perf midi dress that has major spring time vibes! With its short puff sleeves, button front detailing, and flowy feel, this dress is a must for your wardobe.
Fit & Features
- Off the shoulder sweetheart neckline
- Short puff sleeves
- Faux button down front
- Stretchy smocked back
- Front slit | Ruffle hem
- Flowy fit
- Woven fabric | Short knit lining
Style Number/Barcode: 05102-0637
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Look at Her Denim Tunic
You can’t go wrong with this denim tunic! Rock it as a dress or layer it over your favorite matching set.
Fit & Features
- Chest Pockets | Snap Down Front
- Long Sleeves
- Round Hem
- Medium Wash Denim
Style Number/Barcode: 06203-0060
Category Name: Casual Dresses
Price: $18.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Total Babe Sultry Ruched Mini Dress
Hey babe! Get ready to werk it in this sultry ruched mini dress! Featuring a short, curve-hugging silhouette and an allover polka dot print, this little black dress is perf for a date night out. Simply add on some chic mules and you'll be gorgeous from head to toe.
Fit & Features
- Adjustable spaghetti straps
- Scoop neckline
- High waist seam under bust
- Ruched, form-hugging fit
- Dual drawstrings at hem
- Mini length silhouette
- Polka dot printed mesh fabric
Style Number/Barcode: 05102-0636
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Floral Tiered Ruffle Midi Dress
Add a little floral to your wardobe with this gorg tiered ruffle midi dress! Paired with some wedges and sunnies, you'll be ready for brunch with the girls!
Fit & Features
- Adjustable spaghetti straps
- Ruffled square neckline
- Tiered ruffled seams
- Ruffled mid-length hem
- Stretchy smocked body
- Curve hugging fit
Style Number/Barcode: 05102-0634
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Playful In Polka Dots Mini Dress
Get a playful look in adorable polka dots with this LBD! The short puff sleeves make it all the more trendy.
Fit & Features
- Short sheer puff sleeves
- Sweetheart neckline
- Front ruched detailing
- Short, curve hugging fit
- Sheer mesh fabric with all over polka dot print
- Knit lining
- Plenty of stretch
Style Number/Barcode: 05101-0729
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ready Or Not Ruched Mini Dress
Ready or not, you're showing up to slay in this ruched mini dress!
Fit & Features
- Long billowy sleeves | Elastic banded cuffs
- Square neckline
- Complete stretchy smocked back
- Front ruched detailing | Dual drawstrings at hem
- Short, curve hugging fit
- Smooth woven fabric
Pink: Model is 5'8.5" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.
Black: Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0627
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Light And Fresh Cold Shoulder Button Up Tunic
Keep it fresh in a button up! Designed with a touch of feminine, this tunic is per for lunch out, or a celebratory party!
Fit & Features
- Off the shoulder fold over neckline
- Cold shoulder design
- Adjustable spaghetti straps
- Long sleeves that smock at the wrist
- Button down center | Belted waist line
- Mini hemline | Relaxed fit
- Linen like material | Minimal stretch
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.Style Number/Barcode: 06003-0898
Category Name: Casual Dresses
Price: $16.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Ruched To Perfection Midi Dress
This stunning midi dress is ruched to perfection, and will look so gorgeous on you! Paired with some strappy heels, it's totally date night material.
Fit & Features
- Spaghetti straps
- Cowl neckline
- High waist
- Ruched side detailing | Drawstring at hem
- Mid-length, asymmetric hem
- Stretchy knit fabric
- Form hugging fit
Style Number/Barcode: 05101-0727
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Curves Ahead Bodycon Dress
Showcase your curves in this bodycon and flaut a confident look with statement heels!
Fit & Features
- Wired Sweetheart Neckline
- Adjustable Spaghetti Straps
- Lined Jersey Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0633
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Floral Feels Ruffle Mini Dress
Get all those floral feels in this adorable printed ruffle mini dress! Perf to wear to a spring wedding!
Fit & Features
- Strapless sweetheart neckline
- Elastic banded back
- Hidden back zipper | Hook and eye closure
- Ruched detailing
- Tiered ruffle hem
- Floral printed woven fabric | Knit lining
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0632
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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At First Sight Ponte Skater Dress
They'll be falling for you in this twirl-worthy skater dress! Slip into a pair of white sneakers for a charming daytime look and swap them out for block heels just in time for date night!
Fits & Features
- Dual Spaghetti Straps
- Strappy Cross Back Design
- Plunging V Neckline
- Mini Length Hem I Skater Silhouette
- Ponte Fabric
- Moderate Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0726
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Boho Breeze Tiered Mini Dress
Breeze on by like the boho babe you are in this spring ready mini dress! Paired with some strappy sandals, you'll have the best 'fit.
Fit & Features
- Tank-like shoulder straps
- Square neck and back
- Parital button down front
- Hidden back zipper | Hook and eye closure
- Stretchy smocked waist
- Tiered flowy skirt
- Lightweight woven fabric | Woven skirt lining
Style Number/Barcode: 05102-0626
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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This Moment Floral Lace Skater Dress
Stand out for those special moments with a skater dress that captivates with stylish details. The dress features a sleeveless V-neckline with a scalloped lace trim, a floral lace bodice, a sheer lace back, and a skater silhouette. The dress is composed of a combination of crepe and lace fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules and door knocker earrings.
Fit & Features
- Sleeveless V-neckline
- Scalloped lace trim
- Floral lace bodice, sheer lace back
- Skater silhouette
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0624
Category Name: Casual Dresses
Price: $19.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Everyone's Sweetheart Puff Sleeve Mini Dress
You are quite the sweetheart in this fun flirty mini dress! Whether ankle booties are your style, or you are a heels babe both will make this dress pop! The ruching down the center makes her perfect for all body types, and the polka dots keep her fun and lively!
Fit & Features
- Sweetheart neckline | Padded bust
- Puff shoulders
- Long sheer sleeves with polka dot detailing
- Fully lined body with ruching down the center
- Zipper closure center back
- Mesh outer + Moderate stretch
Style Number/Barcode: 05102-0619
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Garden Parties Pleated Midi Dress
Get ready for garden parties, backyard brunches, bridal showers, and spring weddings with this spring staple! Pair with wrap heels, or strappy mules!
Fit & Features
- Tie halter neckline
- Pleated bodice with keyhole cut out
- Smocked stretchy waist line
- Pleated flowy skirt
- Mid-length hemline
- Lightweight sheen polyester material
- Unlined | Moderate stretch
Model is 5'6" with 31" bust, 26" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0724
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Sprung On You Floral Ruched Mini Dress
Have them sprung on you this spring doll! Not only to we love a sweet mini dress because it's cute and flirty, but let's get real, it's an easy effortless outfit! Simply throw on some heels and booties and ur good 2 go!
Fit & Features
- V-neckline
- 3/4 Sleeve length
- Ruched detailing down the sleeves + center
- Ruched detailing lower back to hemline
- Mini skirt lining + Frontal lining at the bust
- Ruffled mini hemline
- Chiffon | Stretch offered at ruched areas
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0606
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Main Girl Ruffled Mini Dress
You are our main girl in a mini dress! Whether you're searching for a bridal piece, or white is just ur color this mini dress is a sweet addition to your closet! Pair with neutral heels and simple earrings!
Fit & Features
- Square neckline
- Spaghetti straps
- Form fitting silhouette| Flattering vertical seams
- Mini hemline with a ruffle trim
- Stretchy woven material
- Hidden zipper center back
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0621
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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As Good As Knit Gets Mini Dress
This chic white knit mini dress is as good as it gets! Paired with some glam earrings and strappy heels, you'll be lookin' fine bb!
Fit & Features
- Spaghetti straps
- Wrap front V neckline
- Ruched side detailing
- Short envelope hem
- Ribbed knit fabric
- Plenty of stretch
Style Number/Barcode: 05102-0620
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bring On The Floral Mini Dress
Bring on the bold floral with this absolutely adorable mini! The dress has a cute ruffle hem for major flirty vibes.
Fit & Features
- Tie shoulder straps
- Slight sweetheart neckline
- Parital stretchy smocked back
- Hidden zipper | Hook and eye closure
- High waist | Flowy short skirt | Ruffle hem
- Woven fabric | Woven lining | No stretch
- All over floral print
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0607
Category Name: Casual Dresses
Price: $15.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Crochet Chic High Low Dress
Keep it cute in crochet girl! This dress is giving us major boho vibes and perfectly pairs with your fav headband and wedges!
Fit & Features
- V-Neckline
- Floral Crochet Bodice
- Adjustable Spaghetti Straps
- Smocked Back
- High Low Silhouette| Mini Skirt Length Knit Lining
- Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0617
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Livin' It Up Ruched Mini Dress
You're out here livin' your best life, and babe we're here for it! Pair this sexy ruched mini dress with some strappy heels for a fun night out.
Fit & Features
- Spaghetti straps
- Square neck and back
- Ruched sides with drawstrings at hem
- Short, curve hugging fit
- Stretchy knit fabric
Style Number/Barcode: 05102-0612
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance