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.

Plus Floral Fiesta Maxi Dress
This beautiful floral maxi dress is perfect for your spring and summer occasions! It features a stretchy off the shoulder neckline with a ruffle pop over, a stretchy high waist seam, and a flowy floor-length skirt. Dress is composed of an unlined crepe fabric with no stretch.
Model is 5'8 with a 42" bust, 35" waist, and 45" hips. She is wearing a size 1X.

Style Number/Barcode: 15102-0033

Category Name: Casual Dresses

Price: $9.97 $45.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Plus Strappy & Stunning Mini Dress
This must-have dress is stylin' and so fab! The mustard yellow asymmetrical dress features a deep V neckline, spaghetti straps, a wrap bodice with ruching on the side, and a wrap skirt with an asymmetrical hem. Dress is composed of an unlined crepe fabric with a moderate stretch.

Style Number/Barcode: 15103-0025

Category Name: Casual Dresses

Price: $9.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Strings Attached Sweater Mini Dress
Get all tied up with this LBD. It features spaghetti straps that lead to a sexy lace-up back, a sweater knit, and a mini length. Dress offers plenty of curve hugging stretch!
Model is 5'9" with a 32" bust, 23" waist and 34.5" hips. She is wearing a size small.

Style Number/Barcode: 06005-6358

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Sleek Style Ribbed Midi Dress
Keep it sleek and stylin' with this yellow ribbed midi dress! It features a deep round neckline, spaghetti straps, and a traditional midi length. Ribbed knit offers plenty of curve hugging stretch.
Model is 5'7" with a 34" bust, 24" waist and 36" hips. She is wearing a size small.

Style Number/Barcode: 06005-6284

Category Name: Casual Dresses

Price: $36.90

Availability: Out of Stock
Product Badge:
- Clearance
Take A Snap Button Midi Dress
You'll want to take tons of snaps for the gram in this button down midi dress! It features a sleeveless bodice, tank-like shoulder straps, gold faux snap buttons, a front slit, and a midi length. The black dress is composed of a ribbed knit fabric with plenty of stretch.
Model is 5'6" with a 34" bust, 24" waist and 37" hips. She is wearing a size small.

Style Number/Barcode: 06005-6300

Category Name: Casual Dresses

Price: $36.90

Availability: Out of Stock
Product Badge:
- Clearance
Crochet Babe Tunic
All you need is sand and sun with this peach crochet tunic! It has a deep V neckline, lined cups, adjustable shoulder straps leading to a low square back, an exposed silver zipper closure, and a comfortable slim fit.Tunic is composed of an unlined crochet 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: 06005-6289

Category Name: Casual Dresses

Price: $5.00 $44.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Ships Free
Fit On Point Sweater Dress
Make your entire 'fit on point with this adorable sweater dress! It features an off the shoulder elastic banded neckline, long fitted sleeves, a narrow belt around the waist with a small gold buckle and gold grommets, and a form hugging fit. The mauve dress is composed of a ribbed knit fabric with plenty of stretch.

Style Number/Barcode: 06005-6214

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Stripe It Right Sweater Dress
Stripe it right with this adorable sweater dress! It features a mini mock neck, short cap sleeves, and a short, curve hugging fit. The white dress is composed of a ribbed knit fabric that offers plenty of stretch and showcases a black and red striped print.

Style Number/Barcode: 06005-6179

Category Name: Casual Dresses

Price: $14.97 $36.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Zipped With Style Knit Dress
Zip your look with style with this trendy knit dress! It features a mini mock neck, long fitted sleeves, a complete zip font with a chic O ring detail, and a belted tie waist. The burgundy dress is composed of a ribbed knit fabric that offers plenty of stretch and a curve hugging fit.

Style Number/Barcode: 06005-6152

Category Name: Casual Dresses

Price: $16.97 $42.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Spiced Up Knit Midi Dress
Spice up your wardrobe in this season appropriate copper midi dress! This cozy sweater dress features an off the shoulder neckline, long fitted sleeves, a comfortable slim fit, and a flatter midi length. Dress is composed of a ribbed knit fabric that offers plenty of stretch.

Style Number/Barcode: 06005-5987

Category Name: Casual Dresses

Price: $15.97 $39.90

On Sale: Yes

Availability: Out of Stock
Product Badge:
- Clearance
Pop Of Stripes Knit Dress
Accentuate those curves with a flattering pop of stripes! This black knit mini dress features an off the shoulder neckline, short sleeves, horizontal pink and white stripes across the bust and hips, and a comfortable slim fit. Dress is composed of a casual knit fabric with plenty of stretch.
Model is 5'7" with a 34" bust, a 24" waist, and 36" hips. She is wearing a size small.

Style Number/Barcode: 06005-0006

Category Name: Casual Dresses

Price: $36.90

Availability: Out of Stock
Product Badge:
- Clearance
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:
- Sale
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:
- Clearance
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:
- Clearance
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:
- Clearance
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:
- Clearance
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:
- Ships Free
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:
- Ships Free
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:
- Clearance
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

Casual Dresses

Now Trending