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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Stylishly Snapped Sweater Dress
This stylish sweater dress is ready for all your snaps! It features an off the shoulder square neckline, long fitted sleeves, a side faux snap button down detail leading to a slit, and a curve hugging fit with a slight asymmetrical hem. The dress is composed of a ribbed knit fabric, offering plenty of stretch.Style Number/Barcode: 06005-0170
Category Name: Casual Dresses
Price: $14.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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All Over Ruffled Skater Dress
Get an adorable all over ruffled look in this pretty little skater dress. It features long sleeves with elastic banded ruffle cuffs, a deep V neckline with a ruffle trim, a hidden back zipper and hook and eye closure, ruffle tiered detailing, and a flowy skater skirt. The dress is composed of a linen fabric with no stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0321
Category Name: Casual Dresses
Price: $18.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Bring Knit On Midi Dress
Bring on the style with this trendy basic knit midi! The dress features a mock neckline, long fitted sleeves, and a mid-length, curve hugging fit. Garment is composed of a brushed knit fabric with a knit lining, offering plenty of stretch.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0178
Category Name: Casual Dresses
Price: $11.97 $29.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Keepin' Knit Basic Midi Dress
Sometimes keeping it basic is the best way to go! This knit midi dress features a sleeveless bodice, tank-like shoulder straps, a scoop neck and back, a side slit, and a mid-length, curve hugging fit. The dress is composed of a stretchy knit fabric.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.
Style Number/Barcode: 05102-0268
Category Name: Casual Dresses
Price: $9.97 $20.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Chic And Spotted Mini Dress
Get a chic and spotted look in this adorable trendy little mini! The dress features an off the shoulder neckline with short cuffed sleeves with ruffle trim detailing, a front keyhole cut out with a tie closure, a stretchy smocked back, and a short, form hugging fit. The dress is composed of a lightweight woven fabric with a cute all over animal print.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0342
Category Name: Casual Dresses
Price: $19.97 $48.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ruffle It Up Smocked Midi Dress
Play up your look with this adorable ruffled and smocked midi dress! It features a sleeveless bodice, adjustable spaghetti straps, a square neck and back with a ruffle hem, ruffle tiers, and a stretchy smocked body with a mid-length form hugging fit. Dress is composed of a lightweight woven fabric.
Model is 5'6.5" with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0341
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Casual Vibes Knit Midi Dress
Get those casual cute vibes in this adorable knit midi! The dress features a V neckline, short sleeves, and a mid-length, curve hugging fit. The ribbed knit fabric offers plenty of stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0315
Category Name: Casual Dresses
Price: $11.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Charm Them All Midi Dress
Charm them all in this casual yet so cute printed midi! The dress features a sleeveless bodice, spaghetti straps, a rounded neckline, and a mid-length, curve hugging fit. The dress is composed of a knit fabric with plenty of stretch.
Model is 5'9" with a 33" bust, 24" waist and 35.5 hips. She is wearing a size small.
Style Number/Barcode: 05102-0252
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Ravishing Ruched Mini Dress
This dress is a daytime delight. It features ruffled sleeves, a hidden back zipper closure, an adjustable drawstring skirt. It's made of a lightweight linen fabric with zero stretch and full lining.
Model is 5'9" with a 32" bust, 24.5" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0243
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Talk That Talk Tank Dress
You're a bad gal, bb! Catch some eyes in this simple-yet-sexy tank dress. Including a racerback neckline that flows into a midi length, this spaghetti tank dress features a smooth, stretchy fabric that hugs your body with every move.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0183
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Necessary Basic Midi Dress
Because we all need this necessary basic midi in our closet! The dress features a sleeveless bodice, spaghetti straps, a square neck and back, and a mid-length, curve hugging fit. The smooth knit fabric offers plenty of stretch for comfortable wear.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 05102-0256
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Girly Gingham Print Ruffled Mini Dress
You love all things girly, so this adorable gingham print mini dress is perfect for you. The all-over smocked design adds stretch, while the ruffled neck and hem bring the cutesy vibe.
Fit & Features
- Smocked cotton fabric, high stretch
- Gingham print
- Sleeveless sweetheart neckline, ruffled trim, small bow detail
- Adjustable spaghetti straps
- Mini-length ruffled hem
- Form-hugging fit
- Runs true to size
Style Number/Barcode: 05102-000160
Category Name: Casual Dresses
Price: $19.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Plus Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining.
Style Number/Barcode: 15102-0018
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Into The Florals Dress
Immerse yourself in all the floral print you can take! This flower bomb features a cowl neck, adjustable narrow straps that create an X back, and a slim fit. Dress is composed of a casual knit fabric with a lightweight feel that offers plenty of stretch. Dress is unlined.Style Number/Barcode: 05102-3105
Category Name: Casual Dresses
Price: $9.97 $31.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Cut Out Mini Dress
This cute and casual cut out mini is perf for your next day out. The dress features an off the shoulder elastic banded square neckline, short sleeves, a trendy front cut out at the waist, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with a knit lining.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0211
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Don't You Want Me Dress
They're gonna want you AND your dress! This tank dress features adjustable shoulder straps with a back tie closure and ruched sides. It's structured with a bodycon fit and hits at the mid-thigh. Fully lined and made of a comfy, textured jersey knit fabric for dressing up or down.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0258
Category Name: Casual Dresses
Price: $9.97 $30.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Simple And Stunning Midi Dress
Simply stunning is what you are in this trendy knit midi dress.
Fits & Features
- Bungee Spaghetti Straps
- Square Neckline
- Curve-Hugging Fit
- Midi Length Silhouette
- Soft Brushed Knit Composition | Fully Lined
- Offers Plenty Of Stretch
Hunter & Mauve: Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Black: Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0175
Category Name: Casual Dresses
Price: $10.97 $28.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Over You Sleeveless Midi Dress
Show us who is boss in sleek midi! This mid length dress features a crew neckline, and a sleeveless bodice. Hem is tailored to a mid calf length, and dress is composed of a ponte material that offers moderate stretch. Throw on some heels and walk the walk!
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0189
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Pretty And Posh Mini Dress
Be the it girl of your squad in this pretty and posh mini! The dress features a sleeveless bodice, a rounded neckline, a square back, and a short, form hugging fit. The dress is composed of a stretchy knit fabric with a full knit lining and showcases a trendy all over plaid print.
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0193
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Charming And Chic Midi Dress
This charming and chic midi dress will turn your look into a classic. It features a sleeveless bodice, a high round neckline, a back zipper closure, flattering vertical seam detailing along the bust, and a mid-length, curve hugging fit. The dress is composed of a ponte knit fabric that offers moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05102-0190
Category Name: Casual Dresses
Price: $9.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Rock On Distressed Tunic Top
Hey, wild child! Show off your spirited side in this distressed tunic top (or be bold and make it a mini!). Top features a crew neck, short sleeves, shredded V detail at chest and hem, and a large "Rock On" contrast graphic. Top is cut for a slim fit and made from an ultra-soft rayon knit with moderate stretch.Style Number/Barcode: 06002-0188
Category Name: Casual Dresses
Price: $9.97 $19.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Summertime Heat Lace-Up Denim Mini Dress
Raise the temps, turning heads in this denim mini dress for a day out or night on the town! The strapless neckline with a front lace-up adds a touch of sexy to the bodycon silhouette that hugs your curves in all the right places.
Fit & Features
- Denim fabric
- Strapless neckline with a front lace-up
- Back zipper closure
- Bodycon silhouette
- Mini-length hem
- Runs true to size
Style Number/Barcode: 05102-000196
Category Name: Casual Dresses
Price: $9.97 $49.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Bad Bee Mini Dress
You're the baddest B in this simple dress. This piece features a crew neckline, short sleeves, and a bodycon fit throughout. It's made of a rib knit fabric that's perfect for dressing up or down.
Model is 5'8" with a 32" bust, 25" waist and 35" hips. She is wearing a size small.
Style Number/Barcode: 06002-0164
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Crochet In Color Dress
This cute crochet dress is perfect for a day out! It features a V neckline, padded cups, adjustable spaghetti straps that create an X back, a sheer crochet waist, and a short flared skirt with a full lining. Dress is composed of a combination lace and gauze fabric that offers a relaxed fit with minimal stretch.*Also available in Plus.
Style Number/Barcode: 05102-3959
Category Name: Casual Dresses
Price: $12.97 $32.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance