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.
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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.
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Fall Nights Satin Button-Up Short Dress
The perfect satin short dress for a night of wine and dining! Featuring long sleeves with buttoned cuffs, a collar neckline, button-up front closures, a smocked waist, and a curved short-length hem. Complete the look in knee-high boots.
Fit & Features
- Long sleeves, buttoned cuffs
- Collar neckline
- Button-up front closures
- Smocked waist
- Curved short-length hem
- Smooth satin fabric, no stretch
- Fits true to size
Style Number/Barcode: 06003-1927
Category Name: Casual Dresses
Price: $13.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Rock Babe Lace-Up Graphic Dress
If you're a rock babe this graphic short dress is the one for you! It features short sleeves, a crew neck, a front lace-up placket, and graphic detail with a script that reads, "Rock N Roll World Tour" along the fitted hem. Complete the look in over-the-knee boots.
Fit & Features
- Short sleeves
- Crew neck
- Front lace-up placket
- Graphic detail/ front reads, "Rock N Roll World Tour"
- Short and fitted hem
- Jersey knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1459
Category Name: Casual Dresses
Price: $6.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Alluring Marble Mesh Bodycon Dress
This alluring marble mesh bodycon dress will draw all the attention your way! It features a square neckline, sheer long fitted sleeves, a short, curve-hugging silhouette, and an all-over marble swirl pattern. The partially lined mesh fabric offers plenty of stretch. Style with platform heels.
Fit & Features
- Square neckline
- Sheer long fitted sleeves
- Mini-length hem
- Fitted bodycon silhouette
- Marble swirl pattern
- Sheer mesh fabric, partial knit lining, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4863
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Finding Inspo Scoop Neck Mini Dress
Casual to dressy, this scoop neck mini dress is perfect for creating all sorts of stylish fits! Featuring long sleeves, a bodycon silhouette, and a slight low-back neckline on ribbed knit fabric. Complete the look in a trendy shacket and booties.
Fit & Features
- Long sleeves
- Scoop neck on front and back
- Bodycon silhouette
- Mini-length hem
- Ribbed knit fabric, double-lined
- Moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4100
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eyes For One Shoulder Sweater Dress
Everyone will only have eyes for you in this one-shoulder sweater dress featuring a long sleeve, flirty choker neck, a side waist cutout, and a form-hugging midi hem with a slit. Pair with strappy stiletto heels to complete the look!
Fit & Features
- One-shoulder, long sleeve
- Choker neck
- Side waist cutout
- Form-hugging silhouette
- Slit midi-length hem
- Soft sweater-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1495
Category Name: Casual Dresses
Price: $6.97 $52.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Laced Up For The Night Mini Dress
Heat up the night in this bombshell sleeveless mini dress featuring v-neckline, tank-style straps, a bodycon silhouette, and a cutout side with lace-up straps. Perfect for styling with strappy stiletto heels.
Fit & Features
- Sleeveless v-neckline
- Tank-style straps
- Bodycon silhouette
- Cutout side with lace-up straps
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4814
Category Name: Casual Dresses
Price: $19.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Live Or Ride Graphic Short Dress
Live life comfortably or on the edge! Showcase your wild lifestyle in this graphic short dress featuring short sleeves, a crew neck, a front script that reads, "Live Or Ride Legend" and a bustier-style bodice with mesh inserts and a fitted hem. Complete the look in combat boots.
Fit & Features
- Short sleeves
- Crew neck
- Graphic front with a script, "Live Or Ride Legend"
- Bustier-style bodice with mesh inserts
- Fitted, short-length hem
- Smooth and stretchy cotton fabric
- Fits true to size
Style Number/Barcode: 06002-1449
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lowkey Head Turner Open Back Mini Dress
She’s simple until she turns around. This bodycon mini dress elevates your look with an open back and tie detail that’s anything but basic. Pair with sandals for daytime outings.
Fit & Features
- Rib knit fabric, smooth, stretchy knit lining
- Crew neck
- Open back with tie detail
- Bodycon fit
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000768
Category Name: Casual Dresses
Price: $29.90
Availability: In Stock
Available Color: BROWN-2
Available Size: XS, S, M, L
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Leave Em' Breathless Sweater Dress
Leave your crush breathless when they see you in this spicy sweater mini dress! It features an off-the-shoulder neckline, long sleeves, a cutout bust, and a bodycon silhouette. Complete the look in thigh-high boots for everyday slay!
Shop More Sweater Styles: The Sweater Collection
Fit & Features
- Off-the-shoulder neckline
- Long sleeves
- Cutout bust
- Bodycon silhouette
- Mini-length hem
- Ribbed-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06005-1456
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cozy Cable Knit Tie-Front Mini Dress
Bring all the cozy vibes this season in this adorable cable knit mini dress! It features a V-neck and back with wrap designs, long balloon sleeves with tapered hems, a high waist with a tie-front accent, and a short, form-hugging fit. Style with knee-high boots.
Fit & Features
- V-neck and back, wrap design
- Long balloon sleeves, tapered hems
- High waist seam, tie-front
- Mini-length hem, form-hugging fit
- Cable knit fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4842
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Me Pretty Ombre Midi Dress
Give your closet some pretty color with this ombre knit midi dress perfect for dressing up! The dress features a sleeveless scoop neck, sleek spaghetti straps, an open lace-up back with tie closure, a bodycon silhouette, and an asymmetrical side slit cutout to showcase some chic strappy heels.
Fit & Features
- Sleeveless scoop neck, spaghetti straps
- Open lace-up back, tie closure
- Bodycon silhouette
- Asymmetrical side slit cutout
- Midi-length hem
- Ombre lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4825
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Draw Attention One-Shoulder Midi Dress
You'll draw all the attention to you in this one-shoulder midi dress perfect for a casual lunch with friends! The dress features a single long sleeve, an adjustable drawstring waist cutout, a side ruched seam, and a form-hugging fit. Complete the look in chic lattice booties.
Fit & Features
- One-shoulder neckline
- Single long sleeve
- Adjustable drawstring waist cutout
- Side ruched seam
- Form-hugging, midi-length hem
- Smooth knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4803
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Made Your Mark X-Back Midi Dress
Make your mark in this stylish basic midi dress featuring a sleeveless crew neckline, wide shoulder straps that cross along the open back, and a form-hugging fit with a side slit detail. Complete the look in pointed-toe heels for a dinner with friends!
Fit & Features
- Sleeveless crew neckline
- Wide shoulder straps cross along the open back
- Form-hugging silhouette
- Side slit detail
- Midi-length hem
- Rib-knit fabric, sewn-in lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4621
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Spirit Chiffon Skater Dress
Play up your flirty side in this adorable chiffon skater dress featuring sheer peasant sleeves, a square neckline, an open-back with tie closure, and a short-length hem. Complete the look in platform heels for a dressy event!
Fit & Features
- Sheer peasant sleeves
- Square neckline
- Open-back with tie closure
- Skater silhouette
- Short-length hem
- Airy chiffon fabric, woven lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-2162
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Casually Cute Ribbed Knit Strapless Mini Dress
Casually cute, this strapless mini dress is perfect for styling from coffee dates to happy hour. The A-line fit adds a flirty flair to the short silhouette.
Fit & Features
- Ribbed knit fabric with knit lining, high stretch
- Strapless straight-across neckline
- Mini-length hem
- A-line silhouette
- Runs true to size
Style Number/Barcode: 05102-000123
Category Name: Casual Dresses
Price: $14.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Step It Up Henley Knit Midi Dress
Step up your basics with this rib knit midi dress with subtle detail for a cute, everyday style! The dress features long sleeves, a V-neck, a button-down front with a slit, and a form-hugging silhouette. Complete the look in strappy mules for weekend plans!
Fit & Features
- Long sleeves, V-neck
- Front button-down
- Slit accent
- Form-hugging silhouette
- Midi-length hem
- Rib knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4726
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Abstract Idea Mesh Printed Dress
Wear your art! This abstract mesh mini dress features a sleeveless square neck, adjustable spaghetti straps, front cutouts with rhinestone button accents, side ruched seams, and a bodycon silhouette. Complete the look in glitzy heels and earrings.
Fit & Features
- Sleeveless square neck
- Adjustable spaghetti straps
- Front cutouts with rhinestone button accents
- Side ruched seams
- Bodycon, mini-length hem
- Abstract print, lined-mesh fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4824
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Knot Pleasure Crew Neck Midi Dress
This crew neck midi dress will be pleased to be added to your fashion closet! It features long fitted sleeves, a form-hugging silhouette, and a front knot accent at the waist. The slinky knit fabric offers a moderate stretch. Complete the look with strappy heels.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Form-hugging silhouette
- Front knot accent at the waist
- Midi-length hem
- Slinky knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4807
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Cream Of The Crop Cutout Mini Dress
Look and feel your absolute best in this prize-worthy casual mini dress! It features a sleeveless, one-shoulder neckline with a thin shoulder strap, a sultry cutout waist with a hoop insert, and a bodycon silhouette. Complete the look in clear strap heels for a lunch date.
Fit & Features
- Sleeveless, one-shoulder neckline
- Thin shoulder strap
- Cutout waist, hoop insert
- Bodycon silhouette
- Mini-length hem
- Double-lined knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4806
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sleek Wonders Square Neck Midi Dress
This sleek midi dress will do wonders for your curves! It features a sleeveless square neckline with bungee spaghetti straps, and a side ruched seam to accentuate your figure along the asymmetrical slit hem. Complete the look in strappy mules for a brunch!
Fit & Features
- Sleeveless square neckline
- Bungee spaghetti straps
- Side ruched seams
- Bodycon silhouette
- Asymmetrical midi slit hem
- Slinky knit double-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4805
Category Name: Casual Dresses
Price: $19.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Cute Weekend Vibes Ribbed Knit Mini Dress
This cute and cozy ribbed knit mini dress is perf for your weekend plans! It features a crew neckline, long fitted sleeves, ruched detailing down the side seams, and a short, curve-hugging silhouette. The soft ribbed knit fabric offers plenty of stretch. Style with knee-high boots to grab coffee with your friends.
Fit & Features
- Crew neckline
- Long fitted sleeves
- Ruching down the sides
- Mini-length hem, fitted bodycon silhouette
- Ribbed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4839
Category Name: Casual Dresses
Price: $19.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Elevated Staple Bodycon Mini Dress
This chic mini dress is an elevated staple! It features a sleeveless mock neckline, tank shoulder straps, and a mini-length, form-hugging, bodycon silhouette. Style with strappy mules and a cute handbag.
Fit & Features
- Sleeveless mock neckline
- Tank shoulder straps
- Mini-length hem
- Bodycon silhouette
- Brushed knit fabric, knit lining
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4663
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Reap The Rewards Cutout Mini Dress
You'll be reaping the rewards of this rib mini dress all season long! It features long fitted sleeves and a crew neckline, a twist accent bust with a cutout waist, side ruched ties that let you customize the length, and a bodycon silhouette. Complete the look in booties.
Fit & Features
- Long fitted sleeves
- Crew neckline
- Twist accent bust, cutout waist
- Side ruched ties to customize the length
- Bodycon mini silhouette
- Ribbed knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4583
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Wildly Iconic Animal Print Long Sleeve Mini Dress
A little wild, a lot iconic—this abstract animal print mini dress brings the heat with its bold vibe and sultry sheer sleeves. Perfect for nights out or when you want your outfit to do all the talking.
Fit & Features
- Sheer mesh fabric with partial knit lining, high stretch
- Abstract animal print
- Mock neckline
- Sheer long fitted sleeves, slit accents
- Mini-length bodycon silhouette
- Short side slit
- Runs true to size
Style Number/Barcode: 05102-000216
Category Name: Casual Dresses
Price: $9.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free