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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Picnic Date Eyelet Lace V-Neck Dress
The cutest picnic date dress ever! Make an adorable impression in this eyelet lace dress featuring a sleeveless V-neck, ruffled straps, and a pencil silhouette on a short hem. Complete the look in wedges.
Fit & Features
- Sleeveless, V-neck, ruffled straps
- Pencil silhouette
- Short-length hem
- Back zipper, hook and eye closure
- Eyelet lace fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05102-4386
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feel The Sun Halter Sweetheart Skater Dress
Bare your shoulders in this cute skater dress on a sunny day! Its easy, breezy design features a halter sweetheart neck, tie-back closure, a ruched bust, and a flowy silhouette and back zipper closure. Composed of seersucker woven fabric with an inner knit lining. Finish the look in lace-up sandals.
Fit & Features
- Sleeveless, halter sweetheart neck, tie-back closure
- Ruched bust
- Flowy skater silhouette
- Above the knee length
- Back zipper closure
- Seersucker woven fabric, no stretch, inner knit lining
- Runs true to size
Style Number/Barcode: 05101-1537
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropic Beauty Strappy Midi Dress
Unveil your beauty on your tropical getaway in this figure-flattering midi dress featuring a square neckline, spaghetti straps, an open strappy back design, and a bodycon silhouette on an asymmetrical midi-length hem. Complete the look in lace-up stilettos.
Fit & Features
- Square neckline
- Spaghetti straps
- Open strappy back design
- Bodycon silhouette
- Asymmetrical midi-length hem
- Tropical print fabric
- Fits true to size
Style Number/Barcode: 05102-4389
Category Name: Casual Dresses
Price: $6.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Lotus Floral Mesh Bodycon Dress
Look lovely in this floral mesh bodycon dress for a trendy afternoon tea look! Features a sleeveless, cowl neckline, adjustable spaghetti straps, on a mini-length hem. Complete the look in cute heels and a straw hat.
Fit & Features
- Sleeveless, cowl neckline, adjustable spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Floral mesh-lined fabric
- Moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4363
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Bora Bora Floral Chiffon Maxi Dress
Got vacay on the mind? This floral chiffon maxi dress is perfect for a trip to Bora Bora! Features a sleeveless, halter neck with tie-closure, ruched bust, and a cutout bodice atop a flowy, tiered maxi skirt. Complete the look in wedges and chic sunglasses.
Fit & Features
- Sleeveless, halter neck, tie-closure
- Ruched bust
- Cutout bodice
- Flowy, tiered maxi skirt
- Floral print
- Airy chiffon fabric, inner lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4391
Category Name: Casual Dresses
Price: $9.97 $54.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Walk Floral Midi Dress
Take a stroll at sunset on your relaxing vacay in this chic floral midi dress. It features a sleeveless V-neckline, adjustable spaghetti straps that lead to a cross-back design, an asymmetrical midi-length hem creating an alluring side slit, and a curve-hugging silhouette. The all-over tropical floral print pairs perfectly with strappy sandals. Complete the look with hoop earrings.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps, cross-back design
- Asymmetrical midi-length hem, ruching, side slit
- Form-fitting silhouette
- Tropical floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4374
Category Name: Casual Dresses
Price: $6.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Weekend Getaway Floral Midi Dress
Pack this adorable floral printed midi dress in your carry-on for your next weekend getaway! It features a sleeveless square neckline, spaghetti straps, ruched detailing down one side leading to a slit, and a midi-length, curve-hugging fit. Style this dress with your fave oversized shades and espadrille wedges.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching down one side leading to a slit, adjustable drawstring
- Midi-length, form-fitting silhouette
- All-over floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4383
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sweet Charmer Floral Mini Dress
You'll be such a sweet charmer in this adorable floral mini dress! It features a scoop neckline with a bust tie, short puff sleeves, ruching down the sides, and a short, form-hugging fit. The brushed knit fabric features an all-over ditsy floral print pattern. Style this dress with espadrille sandals for weekend brunch!
Fit & Features
- Scoop neckline, bust tie
- Short puff sleeves, cinched hems
- Ruching down the sides
- Mini-length, form-fitting silhouette
- Ditsy floral print
- Brushed knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4341
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Chic And Airy Floral Skater Dress
Chic and airy, this floral printed skater dress is ready for all your fun weekend festivities! It features a sleeveless V-neckline, adjustable spaghetti straps, an open back with an adorable tie-back design, and a high waist leading to a short skater skirt with a flirty fit and flare silhouette. Style this dress with strappy mules.
Fit & Features
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Open back, tie closure
- High waist seam, short skater skirt, fit and flare silhouette
- Ditsy floral print
- Sheer woven fabric, full knit lining, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4384
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
- Sleeveless V-neckline
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Rulebreaker Graphic Cutout Short Dress
Break the rules in a mini dress that shows off your bold side! The mini dress features a crew neckline, short sleeves, a graphic that reads: "Breaking The Rules", an image of an eagle with checkered flags and motorcycles, cutout at the back, and a short-length hem. The dress is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch. Complete look with ankle booties and a moto jacket.
Fit & Features
- Crew neckline
- Short sleeves
- Graphic: "Breaking The Rules"
- Image of eagle, motorcycle, checkered flags
- Short length hem, cutout at the back
- Cotton knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 06002-1204
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Socialite Linen Babydoll Dress
The perfect linen babydoll dress for all of your social occasions is here! Featuring a sleeveless square neckline, adjustable spaghetti straps, a fitted bust, and a flared skater silhouette on a short-length hem. Complete the look in cute sandals and a straw bag.
Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Fitted bust, stretchy smocked back
- Flared skater silhouette
- Short-length hem
- Linen woven fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1536
Category Name: Casual Dresses
Price: $9.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Twirl-Worthy Moment Skater Dress
Get ready to have a total twirl-worthy moment in this adorable skater dress. It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, a high waist seam, and a short skater skirt with a flirty fit and flare silhouette. Style this dress with your fave platform heels.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Cross-back, lace-up design, tie closure
- High waist
- Short skater skirt, fit and flare silhouette
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4578
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Floral Tropic Strappy Back Midi Dress
Flaunt your figure on vacay girl! This floral tropic midi dress is perfect for a dinner with a view. Featuring a sleeveless V-neckline, spaghetti straps, a strappy open-back, a bodycon silhouette, and an asymmetrical hem. Complete the look in chic wedges.
Fit & Features
- Sleeveless, V-neck, spaghetti straps
- Strappy open-back, tie closure
- Bodycon silhouette
- Asymmetrical midi-length hem
- Floral tropic print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4376
Category Name: Casual Dresses
Price: $19.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Set the Bar Linen Cutout Mini Dress
This flare mini dress sets the bar high! Showcase your daring side in this sleeveless dress featuring a plunge v-neck on the front and back, a smocked bodice, and side elasticized bar cutouts that lead to a flirty mini-length hem. Complete the look in wedges and dainty earrings.
Fit & Features
- Sleeveless, dual plunge v-neck
- Smocked bodice
- Side elasticized bar cutouts
- Flare mini-length hem
- Linen gauze fabric
- Runs true to size
Style Number/Barcode: 05102-4831
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortlessly Sweet A-Line Mini Dress
Proof that effortless can still be everything. This scoop neck mini dress hugs your curves with a sleek A-line fit—perfect for date night, birthday dinners, or dressy occasions!
Fit & Features
- Structured woven fabric, bust lining
- Scoop neckline, padded bra cups
- Adjustable spaghetti straps
- Back zipper and hook-eye closure
- A-Line silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05101-000104
Category Name: Casual Dresses
Price: $22.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Eyes On You Eyelet Tie Back Dress
All eyes on you in this eyelet lace mini dress! It features puff sleeves, a square neck, a ruched bust, an open back with a tie closure, and a bodycon silhouette. Complete the look in lace-up sandals for a picnic date.
Fit & Features
- Short puff sleeves, cinched hems
- Square neckline, ruched bust
- Open back, tie closure
- Bodycon silhouette
- Mini-length hem
- Eyelet lace fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4438
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Effortless Style Moves Midi Dress
Make effortless style moves in this adorably-chic midi dress. It features a sleeveless square neckline with a ruffled trim, thin ruffled shoulder straps, a stretchy smocked bodice, a high waist, and a flowy, midi-length, A-line silhouette with a front slit. Complete the look with espadrille sandals.
Fit & Features
- Sleeveless square neckline, ruffled trim
- Thin ruffled shoulder straps
- Stretchy smocked bodice
- High waist seam, flowy A-line silhouette
- Midi-length hem, front slit
- Lightweight linen fabric, woven skirt lining
- Runs true to size
Style Number/Barcode: 05102-4347
Category Name: Casual Dresses
Price: $12.97 $59.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Make Way Square Neck Skater Dress
Make way people, you're coming through in this flirty skater dress perfect for graduation! It features adorable short puff sleeves, a square neckline, and a high waist seam that leads to a flowy short-length hem on eyelet knit fabric. Complete the look in cute wedges.
Fit & Features
- Short puff sleeves, elastic ruffled hems
- Square neckline
- High waist seam
- Flowy short-length hem
- Skater silhouette
- Eyelet knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4446
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Playful Floral Mesh Mini Dress
Feeling playful? Brighten up your closet in this floral mesh mini dress perfect for brunch with the girls! It features a sleeveless, v-neck, adjustable spaghetti straps, a bodycon silhouette, center, and sides ruched seams to highlight your curves. Complete the look in lucite heels.
Fit & Features
- Sleeveless, v-neck, adjustable spaghetti straps
- Center and side ruched seams
- Bodycon silhouette
- Mini-length hem
- Floral pattern, back zipper closure
- Mesh-lined fabric, moderate stretch, fits true to size
Style Number/Barcode: 05102-4461
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Farmer's Market Gingham Plaid Dress
Head to the farmer's market looking so cute in this gingham plaid mini dress featuring a sleeveless, v-neck, sleek bungee spaghetti straps, and a bodycon silhouette with a front slit accent. Complete the look in a crop sweater and booties.
Fit & Features
- Sleeveless, v-neck, bungee spaghetti straps
- Bodycon silhouette
- Front slit accent
- Mini-length hem
- Gingham plaid pattern
- Stretchy soft knit fabric
- Fits true to size
Style Number/Barcode: 05102-4452
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cute As A Button V-Neck Midi Dress
You're cute as can be in this v-neck midi dress perfect for a day date! It features long sleeves, a button-down front, midi length hem on a form-fitting silhouette. The rib-knit fabric offers a moderate stretch. Style with chic heels.
Fit & Features
- Long sleeves, v-neckline
- Button-down front
- Midi length hem
- Form-fitting silhouette
- Rib knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4257
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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On Trend Marble Ruched Short Dress
Stay on trend with a short dress that creates a head-turning moment! The dress features a fab marble print, a sleeveless square neckline, spaghetti straps, ruching, and a short-length hem. The dress is composed of a smooth knit fabric that offers a form-hugging fit with a moderate stretch. Complete look with wedges and a cropped denim jacket.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Marble print
- Ruching down the sides
- Mini-length hem
- Lined smooth knit fabric, form-hugging fit, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4455
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Realness Denim Cutout Maxi Dress
Sweet from the front, spicy from the back. With bold cutout accents, a hoop insert, and ruffled tiered flow, this maxi is bringing the drama in the cutest way possible.
Fit & Features
- Denim fabric, sewn-in knit lining
- Sweetheart neckline
- Adjustable spaghetti straps
- Cutout bodice design, hoop insert
- Stretchy smocked back panel, cutout accent, lower zipper and hook-eye closure
- Ruffled tiered maxi-length silhouette
- Runs true to size
Style Number/Barcode: 05102-000131
Category Name: Casual Dresses
Price: $30.97 $68.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Flirty In Floral Chiffon Babydoll Dress
It may start out as flirty but this floral babydoll dress is in for the long haul. It features a sleeveless, ruffle-trim V-neckline, adjustable spaghetti straps, open-back with cross straps, and a fitted bodice atop a tiered, flowy mini skirt. This dress is composed of airy chiffon fabric with an inner lining. Complete the look in chic sandals.
Fit & Features
- Sleeveless, ruffle-trim V-neck, adjustable spaghetti straps
- Open-back, cross straps, fitted bodice
- Hidden back zipper and hook and eye closure
- Tiered flowy mini skirt
- Floral pattern
- Chiffon fabric, inner lining, no stretch
- Runs true to size
Style Number/Barcode: 05101-1474
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale