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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Color Story Square Neck Short Dress
Vibrant and bold, who doesn't want to hear the end of this story? This sleeveless tunic top features an on-trend, square neck, bungee spaghetti straps, a color block pattern, and a bodycon silhouette. Complete the look in large hoop earrings.
Fit & Features
- Sleeveless, square neck, bungee spaghetti straps
- Color block pattern
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1317
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Piece Of Me Crew Cutout Mini Dress
Show off flirty peeks of skin on this sleeveless mini dress featuring a crew neck, bodycon silhouette, and cutout accents along the waist. Complete the look in strappy sandals for happy hour.
Fit & Features
- Sleeveless, crew neck
- Bodycon silhouette
- Cutout accents along the waist
- Mini-length hem
- Brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4735
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Take Me Away Tube Midi Dress
Effortless but still a serve. This strapless knit midi hugs your curves with a twist-front neckline and scalloped hem—perfect for brunches, beach dates, or packing for your next getaway!
Fit & Features
- Texture knit cotton-blend fabric, moderate stretch
- Sweetheart strapless tube neckline
- Twist bust
- Bodycon fit
- Midi-length hem
- Runs true to size
Style Number/Barcode: 06005-000018
Category Name: Casual Dresses
Price: $6.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Summer Love Eyelet Mini Dress
You'll fall in love with the adorable details of this eyelet mini dress! It features a sweetheart neckline with a ruffled trim, a ruched bust with a tie-front, short puff sleeves, and a mini-length, form-hugging fit. The eyelet knit fabric features a lightweight lining. Style this dress with cute espadrille sandals.
Fit & Features
- Sweetheart neckline, ruffled trim
- Ruched bust, tie-front detail
- Short puff sleeves, elasticized hems
- Short, form-fitting silhouette
- Eyelet knit fabric, knit lining, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4433
Category Name: Casual Dresses
Price: $19.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Back Beauty Linen Halter Skater Dress
They'll love to watch you leave in this gorgeous skater dress featuring a sleeveless, halter neck with tie closure, and a smocked bodice that leads to a flowy, skater short silhouette with an open back and lattice bar accents. Complete the look in sleek hoop earrings for a day date.
Fit & Features
- Sleeveless, halter neck, tie closure
- Smocked bodice
- Flowy skater silhouette
- Short-length hem
- Open-back, lattice bar accents
- Linen fabric, lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4404
Category Name: Casual Dresses
Price: $6.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Live Fast Graphic Halter Tunic
A biker babe like you is in need of this graphic tunic! It features a sleeveless, halter neck with tie closure and a front lace-up cutout with graphic detail that reads, "Live Fast/Born To Ride" on a fitted, short-length hem. Complete the look in sleek booties.
Fit & Features
- Sleeveless, halter neck, tie closure
- Front lace-up cutout
- Graphic detail that reads, "Live Fast/Born To Ride"
- Fitted, short-length hem
- Cotton fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 06002-1294
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Lovely In Floral Cowl Mini Dress
You'll look lovely in this floral mini dress featuring a sleeveless, cowl neck, bungee spaghetti straps, and form-fitting silhouette on woven fabric with an inner knit lining. Complete the look in sleek wedges.
Fit & Features
- Sleeveless, cowl neck, bungee spaghetti straps
- Form-fitting silhouette
- Mini-length hem
- Floral print
- Woven fabric, inner knit lining, no stretch
- Fits true to size
Style Number/Barcode: 05101-1576
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Color Story Crepe Mini Dress
Tell the trendiest color story with this fab mini dress! It features a sleeveless, square neck, spaghetti straps, bodycon silhouette, and a color block pattern. Complete the look in sleek hoop earrings for a lunch date.
Fit & Features
- Sleeveless, square neck, spaghetti straps
- Bodycon silhouette
- Mini-length hem
- Color block pattern
- Crepe-lined fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4704
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Fine Lines Chambray Skater Dress
Flirty and fine! Look and feel effortlessly cute in this chambray striped skater dress featuring a sleeveless, v-neck, ruffled trim, and a babydoll-style seam that leads to the flowy short-length hem. Complete the look in braid strap mules.
Fit & Features
- Sleeveless, v-neck, ruffled trim
- Babydoll-style seam
- Flowy short-length hem
- Chambray striped fabric, lining, no stretch
- Back keyhole accent, button closure
- Fits true to size
Style Number/Barcode: 05102-4602
Category Name: Casual Dresses
Price: $19.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Sunset Scene Satin A-Line Dress
Set the scene for drinks at sunset in this satin a-line dress featuring a sleeveless, scoop neck, spaghetti straps, tie-front bust, and a form-fitting silhouette on marble print fabric. Complete the look in lucite heels.
Fit & Features
- Sleeveless, scoop neck, spaghetti straps
- Tie-front bust
- Form-fitting, a-line silhouette
- Mini-length hem
- Marble print, satin fabric, inner lining, no stretch
- Fits true to size
Style Number/Barcode: 05102-4705
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tie Dye For One Shoulder Dress
This maxi dress is totally tie-dye for your next beach day or vacay! Featuring a sleeveless, one-shoulder neck, tank-style strap, high waist seam, and a form-fitting silhouette with a side knot accent atop an asymmetrical hem. Complete the look in cute wedges and shades.
Fit & Features
- Sleeveless, one-shoulder neck, tank-style strap
- High waist seam
- Form-fitting silhouette
- Side knot accent
- Asymmetrical maxi-length hem
- Tie-dye print, brushed knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4622
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Wanderer Paisley Cutout Midi Dress
Embrace the wanderlust life! Look like a babe in this medallion paisley midi dress featuring a sleeveless, v-neck, spaghetti straps, and knot accented bust atop a sultry cutout bodice that leads to the form-fitting midi hem. Complete the look in strappy sandals for a festival.
Fit & Features
- Sleeveless, v-neck, spaghetti straps
- Knot accented bust
- Cutout bodice
- Form-fitting midi hem
- Medallion paisley print
- Crepe knit fabric, moderate stretch
- Fits true to size
Style Number/Barcode: 05102-4342
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charming Florals Chiffon Skater Dress
Charm them all with a floral dress that brings those sweet vibes! The dress features a sleeveless V-neckline, adjustable spaghetti straps, an open-back design with cute tie-back ties, and a skater silhouette. The dress is composed of a lined chiffon fabric that offers a relaxed fit with a minimal stretch. Complete look with wedges.
Fit & Features
- Floral print
- Sleeveless V-neckline
- Adjustable spaghetti straps
- Open back, tie-back ties
- Skater silhouette
- Chiffon fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05101-1100
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Summer Party Paisley Knit Mini Dress
This adorable paisley printed mini dress is perfect for all of your casual summer parties! It features a sleeveless square neckline, spaghetti straps that lead to a lace-up back design, and a short, form-hugging fit. The brushed knit fabric offers plenty of stretch. Style this dress with cute mules.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps, lace-up back design, tie closure
- Mini-length, form-fitting silhouette
- All-over paisley print pattern
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4496
Category Name: Casual Dresses
Price: $9.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Tropical Glam Ruched Short Dress
Keep it glam on your tropical getaway with a mini dress that brings those island vibes! The dress features a tropical floral print, a sleeveless square neckline, spaghetti straps, ruching, and a short length with a rounded hem. The dress is composed of a lined smooth knit fabric that offers a form hugging fit with a moderate stretch. Complete look with sandals and a straw hat.
Fit & Features
- Sleeveless square neckline
- Spaghetti straps
- Ruching
- Tropical floral print
- Short length hem
- Lined smooth knit fabric
- Form hugging fit, moderate stretch, runs true to size
Style Number/Barcode: 05102-4683
Category Name: Casual Dresses
Price: $9.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Falling For Eyelet Mini Dress
Fall for this eyelet mini dress for a cute vibe all summer long! It features a sleeveless, square neck, adjustable spaghetti straps, a flirty tie-front bust, and a form-fitting silhouette. Complete the look in a dainty necklace and wedges.
Fit & Features
- Sleeveless, square neck, adjustable spaghetti straps
- Tie-front along the bust
- Form-fitting silhouette
- Mini-length hem
- Eyelet knit-lined fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4435
Category Name: Casual Dresses
Price: $9.97 $25.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Ruffle Up And Go Tube Romper
Short, sweet, and kinda irresistible. This tube romper flirts with every step thanks to its strapless straight neckline, drop waist design, and adorable ruffled overlay.
Fit & Features
- Ponte knit fabric, moderate stretch
- Strapless straight-across neckline
- Drop waist design
- Tiered ruffled mini-length overlay, A-line silhouette
- Hidden fitted shorts
- Runs true to size
Style Number/Barcode: 06503-000099
Category Name: Casual Dresses
Price: $14.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Perfect Weekend Vibes Mini Dress
This sleek satin floral dress is perfect for your weekend outings! It features a sleeveless V-neckline, spaghetti straps that lead to a cross-back lace-up design, and a mini-length, A-line silhouette. The lightweight satin fabric features an all-over dainty floral print. Style this dress with espadrille sandals.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps, cross-back lace-up design, tie closure
- Mini-length, A-line silhouette
- Dainty floral print
- Smooth satin fabric, no stretch
- Runs true to size
Style Number/Barcode: 05102-4494
Category Name: Casual Dresses
Price: $9.97 $39.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Forever In Floral Mini Dress
They can catch you forever in this floral mini dress! It features a sleeveless sweetheart neckline, spaghetti straps, and a tie-front along the bust on ribbed knit fabric that offers a form-hugging fit. Complete the look in flirty mules for a daytime occasion.
Fit & Features
- Sleeveless, sweetheart neck, spaghetti straps
- Tie-front along the bust
- Form-hugging fit
- Mini-length hem
- Ditsy floral print
- Ribbed-knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4668
Category Name: Casual Dresses
Price: $6.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Vacay Views Floral Midi Dress
Soak in those stunning vacay views in this chic floral midi dress! It features a sleeveless bodice, a wrap-front V-neckline, spaghetti straps, and a curve-hugging, midi-length silhouette with an asymmetrical hem to show some skin. The smooth and stretchy knit fabric features an all-over tropical floral print. Complete the look with strappy heels.
Fit & Features
- Sleeveless bodice, wrap-front V-neckline
- Spaghetti straps
- Fitted midi-length silhouette, asymmetrical hem
- Form-hugging fit
- Tropical floral print
- Knit fabric, plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4441
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Perfect For Paradise Midi Dress
This curve-hugging midi dress is perfect for your vacation in paradise, or to just look like you're on one! It features a sleeveless V-neckline, spaghetti straps, a midi-length asymmetrical hem to showcase some leg, and an all-over tropical floral print to match the vibe of a vacay. Style this dress with strappy mules.
Fit & Features
- Sleeveless V-neckline
- Spaghetti straps
- Midi-length asymmetrical hem
- Form-fitting silhouette
- Tropical floral print
- Knit fabric, moderate stretch
- Runs true to size
Style Number/Barcode: 05102-4474
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Babe Next Door Denim Mini Dress
You'll look like a total babe next door in this adorable denim mini dress. It features a sleeveless sweetheart neckline with a padded bust, thin adjustable straps, an exposed back zipper closure, and a short, form-hugging fit. Style with hoop earrings and trendy cowgirl boots.
Fit & Features
- Sleeveless, sweetheart neckline, adjustable spaghetti straps
- Built-in padded bust
- Back zipper, hook-eye closure
- Mini-length hem
- Form-fitting silhouette
- Denim fabric, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-4448
Category Name: Casual Dresses
Price: $9.97 $42.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Charmed By Ruffles Short A-Line Dress
Get charmed by pretty ruffles in this fab dress! The dress features a square neckline, short puff sleeves, a partially open back with cinching tie-back accent, and a short length with a ruffled hem. The dress is composed of a lined lightweight woven fabric that offers a relaxed fit with minimal stretch. Complete look with mules.
Fit & Features
- Square neckline
- Short puff sleeves
- Partially open back, tie back accents
- Short length
- Ruffled hem
- Lightweight woven fabric
- Relaxed fit, minimal stretch, runs true to size
Style Number/Barcode: 05102-4338
Category Name: Casual Dresses
Price: $9.97 $46.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Feeling Preppy Collared Mini Dress
Your current mood? Preppy and ready for anything with this cute mini dress featuring short sleeves, a collared V-neck, and a bodycon silhouette on rib-knit fabric. Complete the look in trendy boots.
Fit & Features
- Short sleeves
- Collared V-neckline
- Bodycon silhouette
- Mini-length hem
- Rib-knit fabric
- Plenty of stretch
- Runs true to size
Style Number/Barcode: 05102-4412
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale