Casual Dresses
Casual fall dresses that keep up with your plans—coffee runs, brunch dates, weekend hangs, and everything in between. Slip into long-sleeve silhouettes, cozy sweater knits, and soft ribbed jersey styles that make getting dressed feel easy. Go fitted in a bodycon mini, keep it polished with a midi, or lean into a long, flowy shape for an effortless finish. Layer your favorites with the season’s latest jackets for a look that feels warm, styled, and ready for whatever lands on 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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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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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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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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Trendy Cutout Gauze Knit Skater Dress
Keep it trendy with a skater dress that keeps it glam for the season! The dress features a plunging V-neckline, waist cutouts with bar straps, and a skater silhouette. The dress is composed of a gauze knit fabric that offers a relaxed fit with minimal stretch. Complete look with wedges.
Fit & Features
- Sleeveless V-neckline
- Waist cutouts with bar straps
- Skater silhouette
- Gauze knit fabric
- Relaxed fit, minimal stretch
- Runs true to size
Style Number/Barcode: 05102-0246
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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Sweetest Look Floral Off Shoulder High Low Skater Dress
Enchant everyone with the sweetest of looks! Look flowy and fresh in this captivating dress. Complement your attire with cute earrings and a pair of clear strap mules!
Fits & Features
- Off Shoulder Neckline & Sleeves
- Subtle High Low Hem I Skater Silhouette
- Smooth Scuba Fabric I Floral Print
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05101-0142
Category Name: Casual Dresses
Price: $9.97 $38.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Comfy Cozy Slim Hoodie Tunic
Get all those comfy cozy feels in this slim fit hoodie tunic! It features a drawstring hood, long sleeves, a front kangaroo pocket, and a mid-thigh length, relaxed and comfortable fit. The knit fabric offers moderate stretch.
Style Number/Barcode: 06002-0245
Category Name: Casual Dresses
Price: $6.97 $34.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Plant One On Floral Skater Dress
Featuring pretty floral graphics throughout, this fab floral dress is the perfect partner in crime for all your daytime outings.
Fits & Features
- Adjustable spaghetti straps
- Surplice V neckline
- Zipper & hook and eye closure at back
- Removable waist tie
- Wrapped and layered skater skirt
- Crepe composition I Fully lined
- Form-fitting, limited stretch
Model is 5'9" with a 34" bust, 24" waist and 35.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0223
Category Name: Casual Dresses
Price: $9.97 $36.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Flared and Flirty Ponte Skater Dress
Keep it flared and flirty in this twirl-worthy skater dress! Perfectly pair this dress with a set of fab pumps to make a chic impression!
Fit & Features
- V-Neckline
- Spaghetti Straps | Cross-At-Back
- Princess Seams
- Skater Silhouette
- Ponte Knit Fabric
- Form Hugging Fit
- Moderate Stretch
Style Number/Barcode: 05101-0740
Category Name: Casual Dresses
Price: $9.97 $37.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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Cozy Mock Neck Mini Dress
Cozy chic, this mock neck mini is perfect for the season. It features long fitted sleeves and a short, curve hugging fit. The ribbed knit fabric offers plenty of stretch.Style Number/Barcode: 06005-0216
Category Name: Casual Dresses
Price: $10.97 $26.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Ships Free
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Casual Cutie Linen Skater Dress
Get a casual cute look in this lightweight linen skater dress. It features adjustable spaghetti straps, a lined crochet bodice with a V neckline, an open back with a tie closure, and a flowy, skater silhouette. The gauze and linen fabric has a knit lining. Complete your outfit with adorable wedges and a chic shoulder bag.
Fit & Features
- Adjustable spaghetti straps
- Lined crochet bodice with a V neckline
- Open back with a tie closure
- Short skater silhouette
- Gauze and linen fabric with no stretch
- Knit lining
- Runs true to size
Style Number/Barcode: 05102-0233
Category Name: Casual Dresses
Price: $9.97 $44.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale
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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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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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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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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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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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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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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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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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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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Meow You're Talking Leopard Mini Dress
Satin and leopard? Matchmade in heaven. Show your sleek and wild side in the Meow You're Talking mini dress!
Fits & Features
- Cowl Neckline
- Spaghetti Straps
- Adjustable Tie At Back I Low Open Back
- Satin-Like Composition I Minimal Stretch
- Mini Length Silhouette
- Zipper Not Included
Model is 5'9" with a 34" bust, 24" waist and 34.5" hips. She is wearing a size small
Style Number/Barcode: 05102-0338
Category Name: Casual Dresses
Price: $9.97 $35.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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What's Knot To Like Mini Dress
Take your look to the next level with this pretty mini dress! It features an off the shoulder neckline, fitted long sleeves, a cinching tie waist belt with loops and an asymmetrical mini length silhouette with a ruched detailing. Dress is composed of a lined crepe fabric that offers a curve hugging fit with a moderate stretch. Zipper not included.
Model is 5'9" with 32" bust, 24" waist and 34.5" hips. She is wearing a size small.
Style Number/Barcode: 05102-0336
Category Name: Casual Dresses
Price: $12.97 $33.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Clearance
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Vintage Motors Slashed Mini Dress
Give your look some serious edge with this mini dress! It features a round neckline, long fitted sleeves and a mini length silhouette with slashed distressed detailing. The graphic at the center of the bodice features a motorcycle with wings and a graphic that reads: " Superior Motorcycle Vintage Garments." Mini dress is composed of a cotton-blend fabric that offers a curve hugging fit with a moderate stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 06002-0242
Category Name: Casual Dresses
Price: $9.97 $24.90
On Sale: Yes
Availability: Out of Stock
Product Badge:- Sale