Trendy Plaid Dresses You’ll Love for Fall and Winter!

When it comes to fall and winter fashion trends, there’s one trend I’m hooked on this season and that’s plaid, especially plaid dresses. Plaid dresses are uber trendy, versatile and so much fun. You can pair a plaid dress with ankle booties, riding boots, Hunter wellie boots, flat sandals or wedge sandals if you live somewhere warm like California or Florida, slip-on sneakers, Converse Chuck Taylor’s and so much more. You can wear a plaid dress to Sunday brunch with your besties, concerts, out to lunch on the weekends, bridal showers or baby showers, wine tasting with your guy, antique shopping with your mom and so much more. If you’re searching for the perfect plaid dress this season, you’re in luck! I scoured the net and found 36 plaid dresses in every style, color and price range that you’ll adore this fall, winter and beyond!

 

 

Trendy plaid dresses for fall and winter 

 

Casual plaid dresses for fall and winter

Here are a few gorgeous casual plaid dresses that you can dress up or down for fall and winter too! They’ll look amazing with a chic blazer, a leather or suede moto jacket.

 

Rails tops and dresses are my absolute favorite! They are so comfy, cozy and chic. They’re perfect for everyday and can be worn to brunch with the girls on the weekend.

RAILS Nadine Button Down Plaid Dress in Crimson/Dusk
RAILS Nadine Button Down Plaid Dress in Crimson/Dusk

 

 

Madewell is one of my favorite brands for trendy and affordable fashion! This fall I’m loving this black and white plaid dress by the brand. It will look great with ankle boots or wedges.

Madewell Emi Double Weave Plaid Shirt Dress in Black/White
Madewell Emi Double Weave Plaid Shirt Dress in Black/White

 

 

RAILS Nadine Shirtdress in Jet/Charcoal Shopbop
RAILS Nadine Shirtdress in Jet/Charcoal

 

 

This cute plaid dress with three quarter length sleeves will look great with sandals or sneakers.

BB Dakota Ruger Plaid Shift Dress in Multi
BB Dakota Ruger Plaid Shift Dress in Multi

 

 

This best selling blue and white Rails plaid dress is on sale!

RAILS Brooke Button Down Dress in Cobalt Blue/White Check
RAILS Brooke Button Down Dress in Cobalt Blue/White Check

 

 

 

Christophe Sauvat Collection Toronto Dress in Ecru
Christophe Sauvat Collection Toronto Dress in Ecru

 

 

I love everything about this blue and black plaid dress, especially since it has pockets! I can’t get enough of dresses with pockets.

Madewell Jane Plaid Shirtdress in Coastal Blue
Madewell Jane Plaid Shirtdress in Coastal Blue

 

 

My favorite Rails plaid dress is on sale! I love this cheery red, white and blue plaid combo. I own the shirt and it’s my absolute favorite. 🙂

RAILS Brooke Plaid Shirtdress in Cobalt Blue/Cherry/White
RAILS Brooke Plaid Shirtdress in Cobalt Blue/Cherry/White

 

 

Soft Joie Cassina Dress in Garnet Rose
Soft Joie Cassina Dress in Garnet Rose

 

 

Solid & Striped The Shirt Dress in Black Plaid
Solid & Striped The Shirt Dress in Black Plaid

 

 

Fun plaid dress with fringe detail!

Sea Sleeveless Flannel Dress in Multi with Fringe Trim
Sea Sleeveless Flannel Dress in Multi with Fringe Trim

 

 

Socialite Plaid Roll Sleeve Shirtdress in Navy Red Plaid
Socialite Plaid Roll Sleeve Shirtdress in Navy Red Plaid

 

 

 

This chic sleeveless black and white plaid dress will look great with a great moto jacket this fall. It will also be a must come spring.

RED Valentino Scoop Neck Plaid Dress in Grey/Black/White
RED Valentino Scoop Neck Plaid Dress in Grey/Black/White

 

 

Element 'Jessey' Plaid Shirtdress in Maroon
Element ‘Jessey’ Plaid Shirtdress in Maroon

 

 

Chic white collared shirtdress with red, blue and black plaid detailing.

Fraiche by JWoven Plaid Shirtdress in Ivory Tartan
Fraiche by JWoven Plaid Shirtdress in Ivory Tartan

 

 

 

You can’t go wrong with this trendy and affordable fall inspired plaid dress.

Treasure&Bond Popover Plaid Shirtdress in Burgundy Stem Burgundy Plaid
Treasure&Bond Popover Plaid Shirtdress in Burgundy Stem Burgundy Plaid

 

 

Beach Lunch Lounge Belted Plaid Shirtdress in Red Black
Beach Lunch Lounge Belted Plaid Shirtdress in Red Black

 

 

 

Current/Elliott The Twist Shirtdress in Windowpane Plaid
Current/Elliott The Twist Shirtdress in Windowpane Plaid

 

 

RAILS Nadine Long Sleeve Dress in Navy/Plum
RAILS Nadine Long Sleeve Dress in Navy/Plum

 

 

Cheap Monday Flannel Dress in Night Blue Check
Cheap Monday Flannel Dress in Night Blue Check

 

 

Dressy plaid dresses for fall and winter

Who says you can’t wear a plaid dress to the office, church or date night? Here are a few dressy plaid dresses that you are sure to love in a variety of styles and colors.

4.collective Mod Check Dress in Black Multi
4.collective Mod Check Dress in Black Multi

 

 

Woolrich Wool Check Dress in Buffalo Red Check
Woolrich Wool Check Dress in Buffalo Red Check

 

 

Such a pretty plaid fit and flare dress for fall! It will look great with your favorite jacket.

Sanctuary 'Charmer' Check Plaid Fit & Flare Dress in Terracotta Check trendy plaid dresses for fall and winter
Sanctuary ‘Charmer’ Check Plaid Fit & Flare Dress in Terracotta Check

 

 

Burberry Brit 'Wilhelmina' Check Wool Shirtdress in Military Red
Burberry Brit ‘Wilhelmina’ Check Wool Shirtdress in Military Red

 

 

Element 'Isabel' Stretch Knit Plaid Dress in Cobalt Blue
Element ‘Isabel’ Stretch Knit Plaid Dress in Cobalt Blue

 

 

Must have pastel drop waist dress for fall and spring too!

ace&jig plaid Party Frock in Stockholm
ace&jig plaid Party Frock in Stockholm

 

 

cupcakes and cashmere Capra Plaid Dress in Multi
cupcakes and cashmere Capra Plaid Dress in Multi

 

 

Akris Punto Mixed-Media Plaid Dress in Ultramarine
Akris Punto Mixed-Media Plaid Dress in Ultramarine

 

 

 

BB Dakota Jack by BB Dakota Roman Heritage Plaid Dress in Navy Blue
BB Dakota Jack by BB Dakota Roman Heritage Plaid Dress in Navy Blue

 

 

Alexander Wang Formfitting V Neck Plaid Dress in Siren
Alexander Wang Formfitting V Neck Plaid Dress in Siren

 

 

3.1 Phillip Lim Fringed Uneven Hem Dress in Black and White
3.1 Phillip Lim Fringed Uneven Hem Dress in Black and White

 

 

Lela Rose Contrast Panel Dress in Black/Ivory
Lela Rose Contrast Panel Dress in Black/Ivory

 

 

 

Erdem Sleeveless Midi Dress in Blue Multi
Erdem Sleeveless Midi Dress in Blue Multi

 

 

Adore this chic black and white knit dress!

St. John Plaid Knit Sheath Dress in Black-Cream
St. John Plaid Knit Sheath Dress in Black-Cream

 

 

Lanvin Glen Plaid Dress in Ecru
Lanvin Glen Plaid Dress in Ecru

 

 

 

Victoria Victoria Beckham Pleated Midi Dress in Dirty Pink Degrade Check
Victoria Victoria Beckham Pleated Midi Dress in Dirty Pink Degrade Check

 

 

Discover more fall fashion finds in my fall and winter fashion section: https://candieanderson.com/fall-winter-fashion

Candie Anderson®