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.
Now Trending
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.
-
Tortoise O-Ring Ribbed Knit Midi Dress
Casual and cute, you'll be loving the O-ring belt around this chic midi dress! We love to see you rockin' this with some white sneakers and a faux leather jacket!
Fits & Features
-
Spaghetti Straps
- Scoop Neckline I Square Back
- Tortoise O-Ring Waist Belt
- Midi Length Silhouette
- Ribbed Knit Fabric I Fully Lined
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Featured
Style Number/Barcode: 05102-0673
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Spaghetti Straps
-
All About It Ribbed Knit Mini Dress
We're all about our basic essentials and this mini dress is a must! Pair it with some white sneakers for a daytime look or throw on a faux leather jacket and some thigh-high boots for a PM 'fit!
Fits & Features
- Scoop Neckline & Back
- Mini Length Silhouette
- Double Layered Ribbed Knit
- Form Hugging Fit
- Plenty Of Stretch
Style Number/Barcode: 05102-0668
Category Name: Casual Dresses
Price: $9.97 $22.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Flirty Vibes Skater Dress
Give off major flirty vibes and capture some hearts in this adorable double layered skater dress! Keep it casual with some white sneakers or dress it up with some wedges!
Fit & Features
- Adjustable spaghetti straps
- Square neckline
- Open back | Tie closure
- High waistband
- Double layered skater skirt
- Flowy fit
- Woven fabric
Style Number/Barcode: 05101-0747
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Tropical Dream Sleeveless Mini Dress
Dream up the perfect vacation look with a mini dress that channels those vibes! The dress features a sleeveless scoop neckline, adjustable spaghetti straps, lace-up back, a tropical print, 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 wedges.
Fit & Features
- Sleeveless scoop neckline
- Adjustable spaghetti straps
- Lace-up back
- Tropical print
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-0665
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Drawn To You Ruched Mini Dress
Get drawn into this fab mini dress that is perf for your next date night with bae! The dress features a sleeveless sweetheart neckline, a small keyhole with a ruched drawstring, and a mini-length silhouette. The dress is composed of a knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with mules.
Fit & Features
- Sleeveless sweetheart neckline
- Keyhole
- Ruched drawstring
- Mini length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0664
Category Name: Casual Dresses
Price: $6.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Easy Does It Puff Sleeve Ruched Mini Dress
Fall for this sweet mini dress that'll have you ready for the warmer days ahead! Pair with slip-on mules and a cute mini purse for the perf daytime OOTD!
Fits & Features
-
Surplice V Neckline
- Puff, Short Sleeves
- Mini Length Silhouette
- Ruching Along The Sides
- Brushed Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05102-0663
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Surplice V Neckline
-
On My Level Ruched Mini Dress
GIRLLL, they'll want to get on your level as soon as they see you in this! Slip into some pumps to really elevate your look!
Fits & Features
-
Elastic Spaghetti Straps
- Scoop Neckline
- Mini Length Silhouette
- Ruching All Over
- Form Hugging Fit I Plenty Of Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0661
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Elastic Spaghetti Straps
-
Oh So Dainty Ruffle Trim Off Shoulder Ruched Mini Dress
Step right into sunnier days with this charming mini dress! Opt for block heels and a cute mini purse for an eyecatching ensemble!
Fits & Features
-
Ruffle Trim Off Shoulder Design
- Tie Front
- Ruching Throughout
- Mini Length Hem I Full Knit Lining
- Form Hugging Fit I Plenty Of Stretch
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0657
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Ruffle Trim Off Shoulder Design
-
Ribbed Cut Out Sweater Dress
Can't decide what to wear in-between that winter and spring transition? This sleeveless sweater dress is the perf mid-point! Style this look up with some booties or chic mules!
Fits & Features
- Crew Neckline
- Cut Out Design At Center Front Reveals Plunging V
- Sleeveless Bodice
- Mini Length Silhouette
- Ribbed Knit Fabric
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 06005-0613
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Own Knit Open Back Midi Dress
Own your look bb! You know how to werk it, especially in this sultry open back knit midi dress!
Fit & Features
- Mock neckline
- Long fitted sleeves
- Open back | Twist back detail | Lower back cut out
- Curve hugging fit
- Ribbed knit fabric | Plenty of stretch
Style Number/Barcode: 05102-0656
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Gorgeous Getaway Maxi Dress
This stunning printed maxi dress will have you looking absolutely gorgeous for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, a flowy, floor-length silhouette, and a sultry thigh-high side slit. The knit fabric has an all-over tropical palm leaf print, making the dress a perf option for a summer vacay. Style it with wedges and a chic pair of sunglasses.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Floor-length silhouette, high side slit
- Relaxed fit
- Knit fabric, palm leaf print
- Runs true to size
Style Number/Barcode: 05102-0654
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Flirty and Frilly Skater Lace Dress
Keep it flirty and fab in this twirl-worthy skater dress! Pair this must-have dress with pumps and dainty pieces to complete your look!
Fit & Features
- Sweetheart Neckline
- Floral Lace Bodice
- Adjustable Spaghetti Straps
- Lattice Back
- Skater Silhouette
- Lined Crepe Fabric
- Relaxed Fit | Moderate Stretch
Style Number/Barcode: 05101-0738
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Smocked Ruffle Mini Dress
This smocked and ruffled floral mini dress is a major yes. Add to cart and pair with some strappy heels for a nice daytime look!
Fit & Features
- Puff shoulders
- Long sleeves | Smocked detail | Ruffle hems
- Square neckline | Ruffle trim
- Stretchy smocked bodice
- Ruffle details
- Short tiered ruffle hem
- 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: 05102-0649
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Zip Up Chic Mini Dress
Zip up into this chic LBD! Perf for a casual night out with the girls when you want to feel a little dressier than jeans!
Fit & Features
- Collared
- Short sleeves
- Half zip up front
- Short, form hugging fit
- Stretchy knit fabric
Style Number/Barcode: 05102-0650
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Dreamy In Denim Button Front Mini Dress
Look ever so dreamy in denim in this spring ready mini dress! Pair with some wedges and trendy sunnies and you'll be ready to go!
Fit & Features
- Long sleeves | Single buttons to cuff | Puff shoulders
- Sweetheart neckline | Bust seam detailing
- Partial stretchy smocked back
- Button down front
- Slanted front pockets
- Short, form-fitting style
- Jean fabric | Moderate stretch
Style Number/Barcode: 05102-0653
Category Name: Casual Dresses
Price: $9.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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
-
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