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.
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.
-
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
-
Always Sunny Strapless Ruffle Eyelet Mini Dress
This eyelet mini dress is perfect for any sunny day and will be a favorite for shower celebrations, brunch, or graduations! The dress boasts a stretchy smocked bodice that hugs your figure while the ruffled mini-length hem adds a flirty allure.
Fit & Features
- Eyelet woven-lined fabric
- Strapless neckline
- Stretchy smocked bodice
- Ruffled mini-length hem
- Runs true to size
Style Number/Barcode: 05101-4019
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Floral Persuasion Sweetheart Midi Dress
We think we are in love with florals! Fall for this sweet trend in this charming midi dress! Pair with clear heels for a brunch-ready outfit!
Fit & Features
- Sweetheart Neckline | Padded Cups
- Spaghetti Straps
- Floral Print
- Lined Scuba Knit Fabric
- Midi Length Silhouette
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0066
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Go Get 'Em Tiger Print Cowl Neck Mini Dress
Girl, go get em' in tiger print! We will always love our classic leopard print but have been gradually leaning into tiger to change it up and stand out a lil'! Pair with a leather jacket and boots, or black heels!
Fit & Features
- Cowl neckline
- Spaghetti straps that cross in the back
- Mini hemline
- Form fitting silhouette
- Side slit detail
- Lined at the bust | Lots of stretch
- Tiger print pattern
Model is 5'4" with 33" bust, 24.5" waist and 39" hips. She is wearing a size small.
Style Number/Barcode: 05102-0518
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Chiffon Long Sleeve Skater Dress
We're falling for this floral look! It's the perf dress for that special outing you got lined up
Fits & Features
- Surplice V Neckline
- Cuffed & Unlined, Sheer Long Sleeves
- Zipper At Back
- Mini Length | Flowy Skater Skirt
- Lined, Chiffon Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0192
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Get With The Program Crepe Mini Dress
Give them a little attitude when you step out in a mini dress with a little sass! Pair with your go to heels, and a pair of door knocker earrings, and stun in 2020's color of the year!
Fit & Features
- Square neckline
- Bungee spaghetti straps
- Vertical flattering seams
- Mini side slit
- Form fitting silhouette
- Fully lined
- Crepe | 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: 05102-0533
Category Name: Casual Dresses
Price: $11.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Beauty In Floral Skater Dress
Beauty, this floral skater dress was made for you! It features a sleeveless bodice, adjustable spaghetti straps, a deep V neckline, a back zipper and hook and eye closure, a tie front belt, and has a flowy skater skirt. The ivory dress is composed of a crepe fabric with a full knit lining and showcases an adorable floral print.Style Number/Barcode: 05102-0278
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Thinkin' Bout It Floral Cowl Neck Mini Dress
Thinkin' bout those sunny days out at brunch with the galzzz in a cute mini? Well we have the perf dress, the rest is up to you! Pair with a panama hat and booties for that girl-next-door finish!
Fit & Features
- Cowl neckline
- Spaghetti straps
- Form fitting silhouette
- Mini hemline
- Floral ditsy pattern
- Nylon | Stretchy
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0534
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Flirty In Florals Mini Dress
Charm them all in this flirty mini dress! Throw on an oversized denim jacket and some cute heels and you got yourself a lewk
Fits & Features
- Plunging V Neckline & Back
- Short Sleeves
- Mini Length Silhouette
- Knit Fabric With Floral Print
- Form Hugging
- Plenty Of Stretch
Style Number/Barcode: 05102-0373
Category Name: Casual Dresses
Price: $19.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
What's The Ruche Midi Dress
A look we honestly can't get enough of! Slip into this form-hugging midi dress and show off those never-ending curves!
Fits & Features
- Spaghetti Straps
- Square Neckline
- Midi Length Silhouette
- Woven Fabric I Fully Lined
- Ruching Throughout
- Form Hugging Fit I Curve Hugging Fit
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0463
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Button Down Knit Midi Dress
For the modest yet trendy babe! This midi is a closet staple, whether it's work wear or a casual date night, just throw on some heels and you are lookin' gooood bb!
Fit & Features
- V- neckline | Long sleeves
- Oil slick buttons down the center
- Mid-length hemline
- Ribbed knit material
- Moderate stretch
- Form fitting silhouette
Style Number/Barcode: 06005-0516
Category Name: Casual Dresses
Price: $20.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Fever Midi Dress
Get into that floral fever with this adorable ditsy floral printed midi dress, perf for spring!
Fit & Features
- Ruffle spaghetti straps
- Ruffle square neckline
- High waist seam
- Front slit
- Mid-length, flowy fit
- All over ditsy floral print
- Knit fabric | Moderate stretch
Style Number/Barcode: 05102-0455
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
Forever In Love Floral Dress
Be forever in love with florals in this beyond gorg printed dress! Its flowy feel adds a major flirty vibe.
Fit & Features
- Long loose sleeves with single buttons to cuff
- Wrap front V neckline
- Back zipper | Hook and eye closure
- High waist | Tie back detail
- Wrap front tiered skirt
- Sheer floral printed chiffon fabric | Knit lining
Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05101-0527
Category Name: Casual Dresses
Price: $18.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
Floral Passion Scuba Skater Dress
Get passionate about florals this season bby! This twirl-worthy dress is what dreams are made of!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Floral Print
- Double Layered Skater Skirt
- Lined Scuba Fabric
- Relaxed Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05101-0155
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Serving Ruffles Mini Tube Dress
Serving ruffles and bold girl confidence—this tube mini dress does the most. With a curve-hugging fit and layers of mesh ruffles, it's your plus-one for rooftop parties, flirty photo ops, and every standout moment in between.
Fit & Features
- Knit fabric with knit lining, high stretch
- Mesh ruffled design
- Strapless tube neckline, no-slip strip
- Mini-length bodycon silhouette
- Runs true to size
Style Number/Barcode: 05102-000224
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Classy and Chic Asymmetrical Dress
Tie yourself to a classy and chic look in this stunning mini dress! Pair this beauty with fab pumps and a trendy crossbody to complete the look!
Fit & Features
- Square Neckline
- Spaghetti Straps
- Tie Waist Accent
- Asymmetrical Hem
- Lined Crepe Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05102-0460
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Full Bloom Satin Cowl Mini Dress
Spring is just around the corner! Can you believe it? We are ready, satin dresses all season, it's a trend that isn't going away any time soon!
Fit & Features
- Spaghetti straps that cross and tie at the back
- Cowl neckline
- Mini hemline
- Composed of satin | Minimal stretch
- Printed floral design
- Low back
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0458
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sprung On Florals Chiffon Midi Dress
Get sprung over florals this spring! This midi dress is the perfect all occasion piece, whether your going to a shower, a bbq, or brunch, this dress is perf!
Fit & Features
- Scoop drawstring neckline
- Adjustable spaghetti straps
- Milkmaid style bodice
- Fully lined
- Chiffon | Minimal stretch
- Ditsy floral print
- Bust tie detailing | Hidden zipper closure at side
- Mini length
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0467
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Floral Feeling Chiffon Off Shoulder Mini Dress
Bloom, baby! Look absolutely stunning in this floral mini dress!
Fits & Features
- Adjustable Shoulder Straps
- Off Shoulder Neckline & Sleeves
- Layered Ruffles Along Neckline & Hem
- Mini Length Silhouette
- Chiffon Fabric I Lining
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0434
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Floral Dream Corduroy Mini Dress
Keep it dreamy and charming with a pretty floral print! The corduroy fabric on this mini keep this mini feeling luxe and fab!
Fit & Features
- Square Neckline
- Short Sleeves
- Key Hole
- Cross Straps At Back
- Floral Print
- Corduroy Fabric
- Relaxed Fit
Style Number/Barcode: 05102-0481
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
A Classic Ribbed Midi Dress
Look like an instant classic with this curve-hugging sweater dress! The ribbed fabric creates an instant hour-glass illusion!
Fit & Features
- Off The Shoulder Neckline
- Long Sleeves
- Ribbed Knit Fabric
- Midi Silhouette
- Form Hugging Fit
- Moderate Stretch
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 06005-0417
Category Name: Casual Dresses
Price: $6.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Simply Chic A-Line Smocked Dress
Keep it simply chic with a dress that says it all!
Fit & Features
- Elastic Square Neckline
- Tie Front Accent
- Long Sleeve | Elastic Cuffs
- Smocked Waist
- A-Line Silhouette
- Lined Lightweight Woven Fabric
- Relaxed Fit | Minimal Stretch
Style Number/Barcode: 05102-0465
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance