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.
-
Carmela Metallic Shine Party Dress
Special Occasion
You'll be leading the dance floor in our sparkling Carmela! Twist, twirl, and bust a move in her flowy skater skirt while showcasing all the shine from every angle. Style her up with some rhinestone heels and a pair of earrings to match!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust I Mesh Inset
- Mini Length Hem I Skater Silhouette
- Mesh Inset At Back With Triple Row Detail I Back Zipper With Hook & Eye Closure
- Mesh Lined Metallic Threaded Fabric I Fully Lined
- Form Hugging Fit I Moderate Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0417
Category Name: Casual Dresses
Price: $31.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Blissful In Lace Maxi Dress
This gorge lace maxi dress will have you looking and feeling blissful! Don't forget to pair this dress with a fab mini purse and block heels!
Fits & Features
- Crew Neckline I Button Nape & Keyhole Opening At Back
- Sheer Fitted Long Sleeves I Smocked Cuffs
- Sheer Partially Lined Bodice
- Maxi Length Hem
- Lace Fabric I Mini-Length Lining
- Form Hugging Fit I Plenty Of Stretch
Style Number/Barcode: 05101-0760
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
- Crew Neckline I Button Nape & Keyhole Opening At Back
-
Too Dot To Handle Polka Dot Midi Dress
Bb girl, you're sizzling in this dress! Add a pair of cute booties and a faux leather jacket to complement this 'fit!
Fits & Features
- Adjustable Spaghetti Straps
- Surplice V Neckline
- Side Zipper WIth Hook & Eye Closure
- Midi Length Silhouette With Front Slit
- Textured Knit Fabric I Polka Dot Design I Unlined
- Relax Fit I Minimal Stretch
- Zipper Not Featured
Style Number/Barcode: 05101-0761
Category Name: Casual Dresses
Price: $14.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Simply Chic Wrap Front Romper
Simple & chic is your go-to style. This wrap front romper is perf for a daytime look paired with some gold hoops and cute wedges.
Fit & Features
- Short sleeves
- Hidden back zipper | Hook and eye closure
- Wrap front V neckline
- Button closure
- Wrap overlay
- Flowy shorts
- Woven fabric with a short lining | No stretch
Style Number/Barcode: 06303-0068
Category Name: Casual Dresses
Price: $17.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Total Sweetheart Floral Mini Dress
Showcase your sweet style in this adorable floral printed mini dress! It features short sleeves, a V neckline, ruching at the bust with a front drawstring, a small cutout under the bust, and a short, form-hugging silhouette. The unlined knit fabric offers plenty of stretch. Complete your look with dainty earrings and a cute crossbody purse.
Fit & Features
- Short sleeves
- V neckline
- Ruching at the bust with a front drawstring
- Small cutout under the bust
- Ruching down the sides
- Mini-length, form-hugging fit
- Unlined knit fabric with plenty of stretch
- Floral print
- Runs true to size
Style Number/Barcode: 05102-0679
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Lovely In Linen Smocked Mini Dress
Look oh so lovely in linen in this perf springtime mini! The smocked detailing make it all the more flattering!
Fit & Features
- Long sleeves | Smocked cuffs
- Square neck | Eyelet trim detail
- Front tie | Keyhole cut out
- Stretchy smocked skirt
- Short, ruffle hem
- Linen fabric
Style Number/Barcode: 05102-0681
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Pretty In Plaid Mini Dress
Keep it pretty in plaid with this brunch ready mini dress! This season-ready dress only needs a pair of wedges and a pop of jewel tones for a complete look!
Fit & Features
- Square Neckline
- 3/4 Puff Sleeves
- Plaid Print
- Lined Lightweight Fabric
- Mini Length Silhouette
- Relaxed Fit
- Minimal Stretch
Style Number/Barcode: 05102-0680
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Day Dreamin’ Eyelet Mini Dress
Get ready for a sweet summer day in this eyelet dress. Pair it with wedges and a cute mini bag.
Fits & Features
- All Over Eyelet Pattern
- Puff Sleeves
- Lace Up Detailing
- Ruffle Hem
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0678
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flower Power Puff Sleeve Mini Dress
Take on the floral trend with this gorg puff sleeve printed mini! Pair the dress with some espadrille platform sandals and a cute woven bag!
Fit & Features
- Short puff sleeves | Elastic banded cuffs
- Sweetheart neckline
- Back zipper | Hook and eye closure
- Front center ruched detailing
- Short ruffle hem
- Sheer floral printed woven fabric
- Knit lining
Style Number/Barcode: 05101-0756
Category Name: Casual Dresses
Price: $17.97 $45.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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