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.
-
Friday Night Ruched Midi Dress
Get this dress now so you don’t have to worry about not having anything to wear next Friday! It looks great paired with clear heels and layered gold necklaces.
Fits & Features
- Square Neckline
- Ruched Detailing
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0707
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Brunch Babe Floral Mini Dress
We know you love to get cute for brunch with the girls! Style this smocked floral mini dress with white heels and gold accessories.
Fit & Features
- Tie front detail
- Front cut out
- Stretchy smocked body
- Short, form hugging fit
- Ditsy Floral print
- Adjustable Spaghetti Straps
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0744
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
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
-
Friday Night Ruched Midi Dress
Get this dress now so you don’t have to worry about not having anything to wear next Friday! It looks great paired with clear heels and layered gold necklaces.
Fits & Features
- Square Neckline
- Ruched Detailing
- Form Hugging Fit
Model is 5'9" with a 32" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0692
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
That Vintage Look Tunic
Get vintage with it and slip into this cute piece! The slim fit tunic has a basic crew neck paired with a large V cutout front and short sleeves. The stretchy knit fabric is detailed with light distressing and features a large graphic that has the words "Vintage," "Rock and Roll" and "Live fast die young" mixed with a skull and rose image.Style Number/Barcode: 06002-4971
Category Name: Casual Dresses
Price: $6.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Carine Metallic Glitter Ruched Mini Dress
Special Occasion
Almost instantly, Carine's glitter metallic shine will draw eyes your way. You'll be loving her figure-flattering fit that'll have you look and feel amazing. Don't forget to include some stiletto heels and earrings to really finish the look!
Fits & Features
- Adjustable Spaghetti Straps
- V Neckline I Padded Bust
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Ruched Down Center Front, Back & Sides
- Smooth Woven Glitter Knit I Fully Lined
- Form Hugging Fit I Minimal Stretch
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0326
Category Name: Casual Dresses
Price: $36.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Floral Dreams Skater Lace Dress
Dream up the perfect look this season in charming florals! This pretty skater only needs a pair of pretty pumps for a look that's ready for brunch!
Fit & Features
- V-Neckline
- Spaghetti Straps
- Open Back | Floral Lace Back
- Floral Print Pattern
- Skater Silhouette
- Lined Scuba Knit Fabric
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05101-0659
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flirty In Florals Midi Dress
Get a little flirty in pretty florals with this gorg printed midi dress!
Fit & Features
- Adjustable spaghetti straps | Cross back
- V neckline
- Ruched side detailing
- Asymmetric hem
- Mid-length, curve hugging fit
- All over floral print
- Knit fabric | Plenty of stretch
Model is 5'9" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0516
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
A Bold Move Mini Dress
Make a major bold move and absolutely stun in this vibrant mini dress! The bright coral hue is perf for spring break!
Fit & Features
- Bungee spaghetti straps
- Square neckline
- Dart seam detailing
- High waist | Front cut out
- Short, ruffle hem
- Form hugging fit
- Crepe fabric | Moderate stretch
Style Number/Barcode: 05101-0780
Category Name: Casual Dresses
Price: $13.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Leopard Love Lace Up Front Mini Dress
We've all got love for leopard print in our wardrobe! Make your presence be known in this fierce mini dress!
Fits & Features
-
Sheer Roomy Long Sleeves
- Ruffle-Trim At Sweetheart Neckline & Shoulders
- Lace-Up Front
- Back Zipper With Hook & Eye Closure
- Mini Length Hemline I Adjustable Dual Drawstrings At The Front
- Woven Lined Fabric
- Minimal Stretch
Style Number/Barcode: 05101-0768
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Sheer Roomy Long Sleeves
-
Good To Grow Floral Satin Mini Dress
Flaunt the florals cause you look good to go! Go for a sultry look by wearing it off the shoulder or wear the short sleeves up. Slip into your favorite heels and you're all set!
Fits & Features
- Short Sleeves I Can Be Worn Off Shoulder
- Lace Trim Scoop Neckline I Self Tie At Center Front I Keyhole Opening
- Empire Waist
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Satin-Like Fabric I Floral Print
- Form Hugging Fit I Minimal Stretch
Style Number/Barcode: 05101-0459
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flower Of Love Scuba Mini Dress
Brighten up your wardrobe with bold and beautiful floral prints! It's the perf dress for your wedding guest attire!
Fits & Features
-
Wire V Neckline I Vertical Darts At The Bust
- High Waist Seam
- Mini Length Silhouette
- Smooth Scuba Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0191
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Wire V Neckline I Vertical Darts At The Bust
-
Feelin' Slick Satin Puff Sleeve Mini Dress
...And lookin' slick! We are lovin' the puff sleeve trend and know you are too. You'll be lookin' oh-so-chic, everyone's going to think you came off the runway!
Fits & Features
- Square Neckline
- Sheer Mesh Puff Shoulder Short Sleeves
- Back Zipper With Hook & Eye Closure
- Mini Length Silhouette
- Satin Fabric
- Form Hugging Fit I Moderate Stretch
Style Number/Barcode: 05101-0589
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
One Shoulder Asymmetrical Ribbed Maxi Dress
Show off some skin in this cute AF maxi dress!
Fits & Features
- One Shoulder Strap
- Slanted Neckline
- Maxi Length I Sultry Side Slit
- Ribbed Knit
- Form Hugging I Plenty Of Stretch
Style Number/Barcode: 06005-0341
Category Name: Casual Dresses
Price: $17.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Perfectly Stylish Sleeveless Ribbed Knit Midi Dress
Achieve a perfectly stylish everyday look with this sleeveless ribbed knit midi dress! Designed with a comfortable ribbed knit fabric offering plenty of stretch, it features a V-neckline, spaghetti straps, a midi-length hem with a chic high front slit, and a form-hugging silhouette. Pair with a cropped denim jacket and clear mules.
Fit & Features
- Stretchy ribbed knit fabric
- V-neckline
- Spaghetti straps
- High front slit
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 06005-1645
Category Name: Casual Dresses
Price: $7.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
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
-
Knits Not You Crossover Mini Dress
Can you handle knit? Because we can't! This fitted dress is more than a 9-5 piece! Style with a blazer, or long duster for the daytime, then once 5 hits ditch the blazer for ur happy hour attire!
Fit & Features
- Cross over neckline
- Sleeveless
- Form fitting silhouette
- Ribbed knit material
- Moderate stretch
- Mini hemline
Style Number/Barcode: 06005-0495
Category Name: Casual Dresses
Price: $13.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Julissa Knot Front Heat Stone Mini Dress
Special Occasion
Sparkle and glitter like the night sky in our statement Julissa!
Fits & Features
- Plunging V Neckline With Twist Front Design
- Adjustable Spaghetti Straps
- Zipper With Hook & Eye Closure At Back
- Ruching Along The Sides & Center Back
- Mini Length Silhouette
- Fully Lined, Mesh Knit Fabric With Heat Stone Embellishments All Over
- Curve Hugging Fit With Ample Stretch
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Special Occasion products cannot be returned to any retail locations.
Style Number/Barcode: 05001-0249
Category Name: Casual Dresses
Price: $25.97 $69.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Button Down Tie Front Midi Dress
A casual midi dress with chic details! Slip into some mules and you're all set for those daytime festivities with your girls!
Fits & Features
- Bust Tie & Faux Button Front Design
- Short Sleeves I Elastic Cuffs & Shoulders
- Midi Length Silhouette
- Rib Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Style Number/Barcode: 05102-0720
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Square Neck Denim Mini Dress
A casually chic mini dress is a must for any wardrobe! Add a cute cross body purse and slip into some mules for the perf daytime outfit!
Fits & Features
- Square Neckline With Contrast Stitching I Vertical Dart Seams
- Short Sleeves With Elastic Cuffs
- Back Zipper With Hook & Eye Closure
- Mini Length Hem
- Denim Fabric
- Relax Fit I Moderate Stretch
Style Number/Barcode: 05102-0738
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
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
-
Keep It Chic Mini Dress
Keep it simple & chic in this perf LBD! Dress it up with some strappy mules or down with a jean jacket and a casual slip on sneaker.
Fit & Features
- Turtleneck
- Tank-like shoulder straps
- Short, flowy fit
- Crepe fabric
- Plenty of stretch
Style Number/Barcode: 06001-2487
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
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
-
Floral The Right Reasons High Neck
Brunch? Wedding guest? Winery? This floral mini dress is perfect for all these special occasions!
Fits & Features
- Adjustable Spaghetti Straps
- Lace Zipper Back
- High Neckline
- Mini Length Silhouette | Skater Skirt
- Smooth Scuba Fabric With Floral Prints
- Form Hugging Fit | Moderate Stretch
Style Number/Barcode: 05101-0168
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance