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.

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.

That Vintage Look Tunic
Get vintage with it and slip into this cute piece! The slim fit tunic has a basic crew neck paired with a large V cutout front and short sleeves. The stretchy knit fabric is detailed with light distressing and features a large graphic that has the words "Vintage," "Rock and Roll" and "Live fast die young" mixed with a skull and rose image.

Style Number/Barcode: 06002-4971

Category Name: Casual Dresses

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Rock N' Roll Vintage Tunic
Channel your inner rocker with this vintage-inspired tunic! It features a round neckline, a multi strap distressed inset, short sleeves, a contrasting guitar graphic with a block script that reads: "Rock & Rock: Live Fast Die Young" and a distressed detailing throughout. Tunic is composed of a cotton knit fabric that offers a form hugging fit with a moderate stretch.

Style Number/Barcode: 06002-0004

Category Name: Casual Dresses

Price: $6.97 $19.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Can't Relate Henley Mini Dress
Basic? Sorry can't relate. Stand out in this natural mini dress that features a sleeveless bodice, a sweetheart neckline, a multi button down front with wooden buttons, wide shoulder straps and a mini length silhouette. Dress is composed of a lined ribbed knit fabric that offers a form hugging fit with a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 06001-1279

Category Name: Casual Dresses

Price: $22.00 $29.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Simply Stunning LBD
Keep it sleek and stunning in this LBD! It features a sleeveless bodice, a square neckline and wide shoulder straps that lead to an open back design with multi narrow cross straps. The relaxed fit bodice leads to a curve accentuating midi length silhouette. Dress is composed of a ponte-like fabric that offers a moderate stretch.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05103-3528

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spotted In Style Mini Dress
Spotted! You'll be stylin' from head to toe in this fab mini dress. It features a sleeveless bodice, thin shoulder straps, a V neckline, a sultry front waist cut out with a bar accent, and a short, form hugging fit. The leopard print dress is composed of a ponte knit fabric with moderate stretch.
Model is

5’6.5” with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05103-3445

Category Name: Casual Dresses

Price: $13.44 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Swoon Worthy Off Shoulder Mini Dress
Walk right in and watch them swoon all over you in this bodycon mini! Dress it up with some heels and a mini purse to match!

Fits & Features
- Off Shoulder Design & Straps
- Mini Length
- Curved Hemline
- Textured Knit Fabric
- Form Hugging Fit I Moderate Stretch
- Zipper Not Included
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.
Style Number/Barcode: 05103-0747

Category Name: Casual Dresses

Price: $10.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Wrap Around My Heart Dress
You're looking like hot stuff this evening, babes! This dress has a wrap bodice with a deep V neckline, spaghetti straps, and ruching on the side. A wrap skirt creates an asymmetrical hemline for a party perfect ensemble. Dress is composed of an unlined crepe fabric that offers 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: 05103-3609

Category Name: Casual Dresses

Price: $12.97 $31.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Triple Threat Rhinestone Bodycon Dress
No one can mess with this ivory triple threat dress! They won't be able to take their eyes off you with this piece's side cut outs and three sparkling rhinestone bars. Dress has a deep V neckline with a lightly padded bust, narrow cord straps, an invisible back zipper, and princess seams for a longer and leaner illusion. Garment is composed of a thick crepe fabric that offers a moderate stretch. Includes a full lining.

Style Number/Barcode: 05103-2906

Category Name: Casual Dresses

Price: $17.97 $43.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Ruched And Ready Mini Dress
Get ready to go out with the squad in this must have LBD! The black dress features a sleeveless bodice, a square neckline, narrow shoulder straps and a mini length silhouette. The body features ruched detailing throughout to showcase curves! Dress is composed of a lined mesh fabric that offers a moderate stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

Style Number/Barcode: 05103-0177

Category Name: Casual Dresses

Price: $9.97 $40.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Eyes On Me Mini Dress
Demand attention in this Insta-worthy day dress! It features a flirty off-the-shoulder neckline paired with short sleeves. Dress has a round hemline and is composed of a textured knit fabric that offers plenty of stretch.
Model is 5'6" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05103-2257

Category Name: Casual Dresses

Price: $19.97 $28.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Sale
Ruffle Things Up Satin Mini Dress
Make their hearts beat a little faster in this sexy light blue mini dress! It features a sweetheart neckline with a ruffle trim, narrow sleeves with a complementing ruffle trim, bustier style cups with underwire, a hidden back zipper closure, and a body-hugging silhouette. Dress is composed of a lined, satin knit fabric with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05103-0071

Category Name: Casual Dresses

Price: $10.00 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Nautical By Nature Mini Dress
This navy blue and white mini dress is a little naughty, but still sweet! It features a white, sleeveless knit bodice with a V neckline and adjustable shoulder straps. Her A-line skirt has a high paper bag waist with a tie belt, a double row of large buttons on the front, and side pockets.
Model is 5'6.5 with a 32" bust, 23.5" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-4049

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
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Full Scoop Tank Mini Dress
Get the full scoop in this casual cutie! This black knit dress features a scoop neckline, tank-style straps, white stripes running down the sides, and a mini length. Dress is pullover with plenty of stretch.
Model is 5'9" with a 32" bust, 24" waist and 35" hips. She is wearing a size small.

Style Number/Barcode: 05102-4036

Category Name: Casual Dresses

Price: $6.97 $16.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Buttoned And Striped Maxi Dress
Give yourself a cute and casual look with this buttoned and striped maxi dress! It features a sleeveless bodice, spaghetti straps, a scoop neckline, a faux button down front, and a front slit. The black and white dress is composed of a knit fabric with 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: 05102-4028

Category Name: Casual Dresses

Price: $9.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Wrapped In Beauty Mini Dress
Wrap yourself in this gorgeous mini dress to showcase your beauty! The dress features a sleeveless bodice, a wrap V neckline, a tie waist belt and an asymmetrical mini skirt. Dress is composed of an unlined crepe fabric that offers a form 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: 05102-0239

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Twist In Florals Maxi Dress
Give your look a pretty twist in this navy maxi dress! It features a sleeveless bodice, a plunging V neckline, narrow shoulder straps and an open back with tie strap accent. The slim fit bodice leads to a curve hugging maxi length silhouette accented with a high side slit. The all over floral print features pink hues to contrast with the navy background. Dress is composed of a lightweight woven fabric that offers a form hugging fit with a minimal stretch.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small

Style Number/Barcode: 05102-4015

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Beauty In Floral Skater Dress
Beauty, this floral skater dress was made for you! It features a sleeveless bodice, adjustable spaghetti straps, a deep V neckline, a back zipper and hook and eye closure, a tie front belt, and has a flowy skater skirt. The ivory dress is composed of a crepe fabric with a full knit lining and showcases an adorable floral print.

Style Number/Barcode: 05102-0278

Category Name: Casual Dresses

Price: $9.97 $35.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Blooming Beauty Mini Dress
Have a cute brunch with your bffs as you bloom with beauty in this floral mini dress! It features an off the shoulder neckline with an overlay, a high waist seam, and a subtle ruffled seam at the hem. The black dress is composed of an unlined lightweight, flowy linen fabric with no stretch and showcases a pretty pink floral print.
Model is 5'9" with a 32" bust, 24" waist and 34" hips. She is wearing a size small.

Style Number/Barcode: 05102-3981

Category Name: Casual Dresses

Price: $10.00 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Lovely Little Floral Dress
Look oh so lovely in this little floral printed mini dress! It features a sleeveless bodice, spaghetti straps, a square neckline, a lettuce edge trim, and a short, form hugging fit. The natural hued dress is composed of a smocked and stretchy linen fabric and showcases an adorable all over ditsy floral print.
Model is 5'8" with a 32" bust, 23" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3979

Category Name: Casual Dresses

Price: $13.94 $34.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Back In Basics Mini Dress
Fall back on basics for an effortlessly trendy look! This ivory mini dress features a sleeveless strapless bodice, a square neckline, and a short, curve hugging fit. The basic dress is composed of a sheer knit fabric with a full knit lining and 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: 05102-3971

Category Name: Casual Dresses

Price: $10.00 $27.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Casual Cutie Linen Maxi Dress
Go for casual and cute in this taupe dress! It features a V neckline, adjustable narrow straps and a maxi length silhouette with hidden side pockets. Dress is composed of a double lined linen knit fabric that offers a relaxed fit with minimal stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 05102-3966

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
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: 15102-0017

Category Name: Casual Dresses

Price: $9.97 $32.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
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
Fiercely Wild Mini Dress
You're fiercely wild, so you need a dress to match! This mini dress features a sleeveless bodice, spaghetti straps, a scoop neckline, and a short, flattering fit. The dress is composed of a lined knit fabric and offers plenty of stretch and a curve hugging style. Zipper not included.

Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

Style Number/Barcode: 05102-3946

Category Name: Casual Dresses

Price: $9.97 $30.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance

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