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.
-
Tie Dye Frenzy Brushed Knit Mini Dress
Make a splash in a tie-dye dress that brings the style to your next outing! The mini dress features a round neckline, a slash accent on the left side of the bodice, and a tie-dye print. Style this fun print with chunky sneakers and sleek hoops.
Fit & Features
- Round neckline
- Slashed detail on the left side of the bodice
- Short sleeves
- Tie-dye print
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 06002-0581
Category Name: Casual Dresses
Price: $6.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Keeping Knit Retro Tie Dye Ruched Mini Dress
Keep it retro in a tie-dye dress to brighten up your outfits! The mini dress features a mock neck with a zipper front, a tie-dye print, and a mini length silhouette complemented with ruched side seams. Complete your look with clear mules.
Fit & Features
- Mock neck with zippered front
- Long sleeves
- Tie-dye print
- Mini length silhouette
- Ruched side seams
- Form hugging fit
- 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: 05102-1013
Category Name: Casual Dresses
Price: $16.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Keeping Knit Chic Mock Neck Ruched Mini Dress
Keep it chic in a ruched dress that elevates your night out outfit! The dress features a mock neck, fitted long sleeves, and a ruched side drawstring. Complete your night out look with clear heels.
Fit & Features
- Mock neck
- Fitted long sleeves
- Ruched side drawstring
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
Model is 5'7" with a 34" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0904
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Keeping Knit Real Ruched Mini Dress
Keep it real in this chic mini dress for your next outing with the squad! The dress features a crew neckline, ruched side seams with drawstrings at the hem, and a curve-hugging mini-length silhouette. Complete your look with mules.
Fit & Features
- Crew neckline
- Long sleeves
- Ruched side seams
- Drawstrings at the hem
- Mini-length silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
Style Number/Barcode: 05102-0921
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Major Influence Mock Neck Ruched Mini Dress
Hey, trendsetter! Stun in this mini dress that is so chic and casual! The mini dress features a sleeveless mock neck, a ruched body and a mini length silhouette that hugs curves in all the right places. Style with chunky sneakers to nail those lowkey vibes.
Fit & Features
- Sleeveless
- Mock neck
- Ruched body
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0886
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Feline Fashionista Leopard Mesh Mini Dress
Keep it fierce in a leopard dress that shows off your affinity for style! The mini dress features a leopard print, a sleeveless square neckline, and sleek spaghetti straps. Complete your night-out look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Leopard print pattern
- Mini-length silhouette
- Lined mesh fabric
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-0927
Category Name: Casual Dresses
Price: $9.97 $27.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Get Knit Right High Slit Maxi Dress
Get your look right in a knit dress that is perfect for keeping it casual! The dress features a sleeveless crew neckline and a maxi length silhouette with a high side slit. Complete your look with chunky sneakers for a cute coffee run outfit.
Fit & Features
- Crew neckline
- Sleeveless
- Maxi length silhouette
- High side slit
- Smooth knit fabric
- Relaxed fit, moderate stretch
Style Number/Barcode: 05102-0883
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Pretty In Plaid Woven Mini Dress
Keep it pretty in a plaid dress that is so on trend this season! The dress features a sleeveless square neckline, a plaid print, and a mini length silhouette. Complete your cute date night look with black mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Plaid print
- Woven fabric
- Mini length silhouette
- Form hugging fit
Style Number/Barcode: 05102-0891
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Lovin' Knit Basic Midi Dress
We love a knit dress to keep on trend this season! Throw on this must-have dress for a casual day out. The dress features a trendy square neckline, fitted long sleeves, and a midi length silhouette. Complete look with chunky sneakers for a casual vibe.
Fit & Features
- Square neckline
- Long sleeves
- Midi length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0853
Category Name: Casual Dresses
Price: $9.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Good Vibes Basic Ribbed Knit Maxi Dress
Bring the good vibes in a maxi dress that can be dressed up for a chic day out. The dress features a scoop neckline, sleek bungee straps, and a maxi length silhouette with a high side slit. Style dress with chunky sneakers and sleek hoops.
Fit & Features
- Sleeveless scoop neckline
- Bungee spaghetti straps
- Maxi length silhouette
- High side slit
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0863
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Buttoned In Sassy Stripes Midi Dress
Button up in a striped dress that keeps your look so casually cute! The dress features a fab button-down front, tie spaghetti straps, and a striped pattern. Complete your look with clear mules for a stylish look.
Fit & Features
- Sleeveless scoop neckline
- Tie spaghetti straps
- Button-down front
- Striped pattern
- Midi length silhouette
- Knit fabric
- Form hugging fit, moderate stretch
Style Number/Barcode: 05102-0569
Category Name: Casual Dresses
Price: $9.97 $23.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
She's A Showstopper Ruched Midi Dress
Make them stop and stare at this stunning dress that commands attention! The sleek midi dress features a trendy square neckline, sleek bungee straps, and a curve-hugging ruched midi silhouette. Complete your look with duster earrings for your night-out outfit.
Fit & Features
- Sleeveless square neckline, bungee straps
- Strapless bra recommended
- Side ruched detailing
- Midi-length bodycon silhouette
- Smooth knit fabric
- Form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-0848
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Keeping Knit Casual Off the Shoulder Ribbed Mini Dress
Keep it casual and fab in a mini dress that is so easy to style for your next day out with the squad. The dress features an off the shoulder neckline with a popover detail and composed of a ribbed knit fabric that enhances curves with a moderate stretch. Complete your casual outfit with ankle booties and hoop earrings.
Fit & Features
- Off the shoulder neckline
- Popover detail
- Mini length silhouette
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0859
Category Name: Casual Dresses
Price: $12.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
So Into You Basic Knit Midi Dress
We're so into this dress that can be dressed up for a date night or keep it casual with layers. The dress features a sleeveless square neckline, tank-straps that offer support, and a curve-hugging midi-length silhouette. Complete look with ankle booties or mules.
Fit & Features
- Sleeveless square neckline
- Tank straps
- Midi length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0912
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Western Style Horse Tapestry Mini Dress
Channel that western-chic style in this mini dress designed with a detailed horse tapestry fabric. The lace-up back offers a customized fit, while the short A-line silhouette is perf for pairing with cowboy boots.
Fit & Features
- Horse tapestry woven fabric, no stretch, knit lining
- Strapless straight-across neckline, no-slip strip
- Lace-up back design
- Lower back cutout, hidden zipper with hook-eye closure
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000200
Category Name: Casual Dresses
Price: $9.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Bohemian Chic Lace Off-The-Shoulder Skater Dress
Channel that bohemian chic aesthetic in this airy sheer lace skater dress featuring an off-the-shoulder straight neckline with a fold-over design and sheer long fitted sleeves. The trendy V-shaped drop waist seam leads to a short uneven hem with a flowy skater silhouette.
Fit & Features
- Sheer lace fabric with partial knit lining, plenty of stretch
- Off-the-shoulder straight neckline with fold-over design
- Sheer long fitted sleeves
- V-shaped drop waist seam
- Short uneven hem
- Skater silhouette
- Runs true to size
Style Number/Barcode: 05101-3714
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Slay Every Day Basic Scoop Neck Midi Dress
Slay every day in a basic midi dress that is effortlessly chic. The dress features a sleeveless scoop neckline, tank-straps, and a midi length silhouette. The double lined smooth knit fabirc offers a comfortable feel. Complete your look with chunky sneakers and stud earrings to nail low-key vibes.
Fit & Features
- Sleeveless scoop neckline
- Tank-straps
- Midi length silhouette
- Double lined smooth knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0908
Category Name: Casual Dresses
Price: $19.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
-
Essential Ribbed Tube Mini Dress
Keep it casual in a tube dress that keeps your look effortlessly on point. The dress features a sleeveless straight neckline and a tube silhouette. Complete look with sneakers and shimmering hoops.
Fit & Features
- Sleeveless square neckline
- Tube silhouette
- Mini length
- Ribbed knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0887
Category Name: Casual Dresses
Price: $12.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Every Day Basic Knit Mini Dress
Keep cute in a basic mini dress that is perfect for dressing up or dressing down for a casual day out. The dress features a sleeveless square neckline, tank-like straps that offer support, and a mini length silhouette. Complete your casually cute outfit with sneakers and door knocker earrings.
Fit & Features
- Sleeveless square neckline
- Tank-like straps
- Mini length silhouette
- Knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0854
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Off The Shoulder Ribbed Cutout Mini Dress
Stun in a mini dress that showcases curves in all the right places. Perfect for your next date night, this ribbed dress is a must! The dress features an off the shoulder neckline, fitted long sleeves, and a mid-drift cutout to show off a hint of skin. The dress is composed of a ribbed knit fabric with vertical seams that streamline the silhouette. Complete your night out outfit with hoop earrings.
Fit & Features
- Off the shoulder neckline
- Fitted long sleeves
- Mid-drift cutout
- Vertical seams
- Ribbed knit fabric
- Form hugging fit
Style Number/Barcode: 05102-0820
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
In Knit For A Good Time Basic Mini Dress
Throw on this basic mini dress and let the good vibes flow! This knit dress is perfect to dress up or dress down for your next date night or for GNO with the squad. The dress features a trendy square neckline, sleek bungee straps, and a mini-length silhouette. Dress up with mules or keep it casual in sneakers.
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Mini length silhouette
- Smooth knit fabric
- Form hugging fit
- Moderate stretch
Style Number/Barcode: 05102-0873
Category Name: Casual Dresses
Price: $19.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
-
Chic Ribbed Knit Basic Mini Dress
Basic yet still so chic, this ribbed knit mini dress is an everyday essential! It features a doubled ribbed knit fabric for comfortable wear and a form-hugging fit to enhance your curves. Pair this adorable dress with some chunky sneakers to get that effortless vibe.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Short, form-hugging fit
- Doubled ribbed knit fabric
Style Number/Barcode: 05102-0841
Category Name: Casual Dresses
Price: $9.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Flowy Fall Feels Off The Shoulder Tunic
Get those fall feels in this adorable flowy off the shoulder tunic! It features long flowy flared sleeves and a cinched elastic waist. The lightweight woven fabric features a gorgeous allover bohemian floral print. Pair this tunic with some heeled mules for the perfect date night look.
Fit & Features
- Off the shoulder boat neckline
- Long flowy flared sleeves
- Cinched elastic waist
- Short, ruffle hem
- Woven fabric with allover floral print
Style Number/Barcode: 06003-1017
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
-
Live It Up Tie Dye Knit Mini Dress
Live it up in this majorly on-trend tie dye mini dress! Featuring a chic lace-up back and a curve-hugging fit, this dress is perf to make a stylish statement at your next brunch. Simply pair it with some clear mules for a gorgeous look.
Fit & Features
- Scoop neckline
- Spaghetti straps leading to a lace-up back
- Short, form-hugging fit
- Tie dye knit fabric
Style Number/Barcode: 05102-0884
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance