Menswear Designers Are Mad for Plaid: These Are the 25 Best Men’s Plaid Shirts (and a Bit More) For Fall 2020

Men's Plaid Shirts
Courtesy of Everlane & Urban Outfitters

This summer, tie-dye was everywhere. Soon, you’re going to be seeing a new pattern taking over the fashion world — plaid. You may have noticed that plaid is appearing on everything from sneakers to hats. Yes, plaid is always a perennial fall favorite pattern, but this year it’s showing up everywhere. Menswear designers like Nicholas Daley, Woolrich, Etro, Dolce & Gabbana and more are using plaid clothing in every iteration of their runways for Fall 2020. What does that mean to the average guy? Welp, you might end up with a few more men’s plaid shirts and pants in your closet than usual. If you’re a trendsetter, you’re already waiting for that plaid Gucci shirt to hit store shelves.

In this piece, we’re going to break down the differences between checks, plaid and flannel, help you find the best men’s plaid shirts for fall, and offer some stylish plaid pants and accessories. If you’re ready to start filling up your closet with plaid, keep scrolling for our favorite plaid menswear of the season. Or, you can keep reading to learn more about this timeless pattern.


Is there a difference between flannel and plaid?

Yes, there is definitely a difference, even if it’s irrelevant to the average shopper. You can wear flannel shirts, you can wear plaid shirts, and you can wear plaid-flannel shirts, too. Flannel is a type of fabric. Originally made from wool, now you can find it in cotton, cotton blends or synthetic materials. One side is soft and fuzzy, and the other side is usually a bit rougher. On the other hand, plaid is the name of a pattern, which features a blend of perpendicular horizontal and vertical lines of varying thickness and color. However, since most flannel shirts feature a similar pattern of checks, these terms are sometimes used interchangeably by shoppers.

While a plaid shirt will always feature a plaid print, a flannel shirt could feature plaid, gingham, checks or even a solid color.

Here’s a flannel shirt that doesn’t qualify as plaid:

close up of flannel shirt Licensed from Adobe

And here’s a flannel-plaid shirt:

men's flannel-plaid shirt Licensed from Adobe

Are plaid and checks the same type of pattern, or are they different?

A lot of fashion designers and shoppers will use the terms “plaid” and “checks” interchangeably. While they look similar, they’re not exactly the same. Plaid is created by crisscrossing lines of various widths, whereas check patterns are more uniform in size. For most people, when they hear the word “plaid,” they think of classic Tartan plaids. Traditionally, many Scottish clans and families had their own tartan plaid to identify themselves, but today you’ll find tartan in a wide range of styles and apparel. If you do a web search with either “check shirt” or “plaid shirt,” most of the time you’ll find the same shirts under either designation. For the sake of everyone’s sanity, let’s not waste too much time splitting hairs.

How to style men’s plaid shirts and apparel

The great thing about the best plaid shirts for men is that they come in as many color combinations as you can think of. Depending on the fabric and the cut of the shirt, you can wear a tailored plaid shirt with trousers to a formal workplace or event. You can also throw on a looser cut plaid shirt over a graphic tee, add jeans and you’ve got something you can wear to a concert. It’s a versatile print, which is one reason it’s popular with designers and consumers alike.

Because plaid has a personality, it’s a very noticeable print. Hopefully, you know that you shouldn’t be mixing patterns, which means you should stick to one piece of plaid clothing at a time. There is one notable exception to this rule: it’s acceptable, and quite trendy, to wear a plaid suit, so long as your slacks and blazer match perfectly. Outside of that context, mixing plaids is a very risky choice. Either match plaids that have the same colors or mix a small plaid print with a larger one.

If you like the “idea” of plaid but aren’t sure if it’s right for your personality, you can integrate the pattern into your wardrobe by taking baby steps. Look for plaid accessories like belts, socks, wrap bracelets or even boxers. You can also start with something familiar like a red flannel shirt. Start off with something simple, or be a little more daring and carry a plaid backpack. Like most men’s fashion trends, the more you wear men’s plaid shirts, pants and accessories, the more you’ll get used to them.


The Best Men’s Plaid Shirts for Fall/Winter 2020

Ready to rock a plaid shirt? We’ve put together a list of our favorite men’s plaid shirts for the season. We’ve included a mix of both traditional plaid and plaid-flannel shirts, so there should be something for everyone. Below, you’ll find a few extra goodies, including men’s plaid pants and accessories.

1. Madewell Brushed Cotton Easy Camp Shirt


If you hate the cold, you’ll probably love this shirt. Madewell recently launched a menswear line, and we’ve already become big fans of their everyday casual men’s clothing. Madewell designed this flannel shirt in brushed cotton flannel for extra comfort, and it features a lighter autumn gold plaid pattern that will pair well with almost anything. Cut to be worn untucked, it can double as a light shirt jacket.

Best Men's Plaid Shirts: Madewell Brushed Cotton Easy Camp Shirt Courtesy of Madewell


2. VINCE Window Plaid Long Sleeve Shirt


Window plaid, also known as windowpane plaids (same thing, just a different name), are plaids where the crisscrossing lines are wider or bigger, and therefore resemble a windowpane. When done in dark shades like this one from VINCE, it’s a tad more formal and sophisticated than other plaids. This is a classic-fit shirt with a curved hem, and it’s one of the most stylish plaid shirts for men you’ll find this season.

VINCE Window Plaid Long Sleeve Shirt Courtesy of Vince


3. ASOS Design Stretch Slim Shirt in Yellow And Navy Check


When starting out with plaid, opt for a shirt that’s not too busy or bright, like this navy and yellow plaid shirt from ASOS. The neutral hues won’t make you feel overwhelmed. The tones in the shirt make it easy to pair with jeans of any shade, and it’s nicely tailored, too. The slim cut means that it can be worn to work with casual trousers or jeans. Need to make a statement? Try this plaid shirt with a solid navy tie and corduroy pants.

ASOS DESIGN Stretch Slim Shirt in Yellow And Navy Check , Best Men's Plaid Shirts Courtesy of ASOS


4. Burberry Beige Flannel Vintage Check Shirt


It sometimes feels that Burberry’s fashion house is based on one plaid, the iconic “Nova Check.” Actually, the brand has quite a few plaids that they use in designs. Their Caxton checked plaid was used for years as the lining in their legendary raincoats, for instance. This neutral-toned plaid with sparks of red is a statement maker as it’s instantly recognizable as a Burberry plaid.

Burberry Beige Flannel Vintage Check Shirt, Best Men's Plaid Shirts Courtesy of SSENSE


5. Everlane Brushed Flannel Shirt


Made for total comfort, this brushed flannel from Everlane has chilly temps written all over it. It’s an effortlessly handsome throw-on for cold days and will look awesome with just about anything you wear with it. Each shirt is made with 100% cotton and is totally durable to take on any and all of your days. It’s also totally abrasion-resistant, so you can truly get a lifetime out of it.

Everlane Brushed Flannel Shirt Courtesy of Everlane


6. BDG Heavyweight Flannel Overshirt


Ditch the classic colors affiliated with plaid for something a bit more out there. Never have we ever seen a plaid shirt boasting a color as bright as this orange, but man, are we excited to see it. BDG offers a number of products at Urban Outfitters that are both durable and cool for just about any kind of day. Rock this shirt with your favorite BDG jeans and stunt a whole Urban outfit no one’s prepared for.

BDG Heavyweight Flannel Overshirt Courtesy of Urban Outfitters


7. Goodthreads Plaid Oxford Shirt


Whoa! A well-made plaid shirt for under $20? Goodthreads is one of Amazon’s own brands, and they have a plethora of affordable menswear deals. This navy, white and red tartan plaid is one of the classic plaids that most people think of when they hear the “p” word. It also comes in 25 other plaid patterns!

Goodthreads Plaid Oxford Shirt Courtesy of Amazon


8. Wrangler Authentics Long Sleeve Heavy Weight Fleece Shirt


If you’ve ever owned a pair of Wrangler jeans, you won’t be surprised to know that this Wrangler flannel is a durable as hell shirt to get you through the winter. Stay warm, comfortable and stylish rocking this bad boy around town no matter the occasion. It is immensely durable and it’s built to last, so you’ll look cool and never have to worry about replacing this.

Wrangler Authentics Long Sleeve Heavy Weight Fleece Shirt Courtesy of Amazon


9. Standard Cloth Shadow Plaid Flannel Button-Down Shirt


This soft cotton blend flannel shirt boasts a subtle shadow plaid and has a worn-in “had it forever” feel all the way down to the buttons. Cut slightly full, so it could be easily worn over a long sleeve tee, it has one chest pocket.

Standard Cloth Shadow Plaid Flannel Button-Down Shirt Courtesy of Urban Outfitters


10. Eddie Bauer Eddie’s Favorite Flannel Relaxed Fit Plaid Shirt


One can’t do a plaid shirt roundup without including something from the legendary Eddie Bauer. It’s one of the oldest outdoor outfitters around, and a plaid flannel shirt from them is like owning part of a legend.

Eddie Bauer Eddie's Favorite Flannel Relaxed Fit Plaid Shirt Courtesy of Eddie Bauer


11. Amazon Essentials Flannel Shirt in Olive Plaid


If you’re not a fan of olive, there are 30 other plaid flannel shirts, including orange, yellow and gray-on-gray checks in the Amazon Essentials collection. It’s a mid-weight flannel that keeps you warm on chill autumn mornings. The shirt has a classic fit, so it’s slightly full and boxy.

Amazon Essentials Flannel Shirt in Olive Plaid Courtesy of Amazon


12. Volcom Caden Plaid Long Sleeve Flannel Shirt


Bring that surf’s up aesthetic to your fall look by rocking sea-centric shades of blue and green this season. Made from cotton, this soft flannel shirt has a tiny logo on the chest pocket. And you thought Volcom only did surfwear.

Volcom Caden Plaid Long Sleeve Flannel Shirt Courtesy of Amazon


The Best Men’s Plaid Everything Else for Fall/Winter 2020

From pants and bags to scarves and sneakers, if you really want to go all-in on plaid (and, heck, you should), these are the pieces to cop this year.

13. Banana Republic Slim-Fit Glenn Plaid Trouser


These pants feature a very subtle navy Glen Plaid — that’s a plaid comprised of very small and somewhat larger checks, so at first glance it looks almost solid. These men’s plaid pants have a tapered silhouette. They’re wider at the thigh and then narrow down to the ankle, so you’ll keep a totally stylish look in the forefront while staying quite comfortable in these all day through.

Banana Republic Slim-Fit Glenn Plaid Trouser Courtesy of Banana Republic


14. Original Penguin Original Pengjuin Retro Plaid Stretch Cotton Pants


Cut like classic trousers, and made with stretch cotton, these pants are done in Black Watch plaid to give you that retro feel that you cherish so dearly. Because the pants are in a traditional and easily recognizable plaid, they’ll never go out of style. They can be worn for work or you can dress them down with a chunky fisherman’s sweater and Doc Martens.

Berle Flat Front Classic Fit Plaid Wool Trousers Courtesy of Nordstrom


15. GINGTTO Plaid Chinos


Add a lack of breathing room to your favorite plaid pants by snagging yourself these tight yet handsome plaid pull-on chino joggers from Amazon. These are excellent for both work and play. They’re detailed with the classic chino fabric you’ve come to know and love at this point and are tapered tremendously to hug your buns and thighs just the way you want them. So, what are you waiting for? They’re right in your piece range, big guy.

GINGTTO Plaid Chinos Courtesy of Amazon


16. Polo Ralph Lauren 2-Pack Bear Plaid Socks


Not ready to go the whole hog with the plaid trend this season? You can dip your toe into it with this practical set of plaid socks. One pair is red plaid, perfect for showing off your sophisticated style when you cross your legs. The other pair is in staid black that’s livened up with a tuxedo-wearing teddy bear.

Polo Ralph Lauren 2-Pack Bear Plaid Socks Courtesy of Amazon


17. Herschel Classic XL Backpack in Quiet Shade


Need a backpack to tote your laptop and various things? Herschel’s become the go-to backpack for everyone. Probably because they offer a lifetime warranty on all their bags. This extra-large backpack has outer zippered compartments and a spot for a water bottle. And the pattern is a refined tonal gray on gray plaid.

Herschel Classic XL Backpack in Quiet Shade Courtesy of Amazon


18. Golf Belt with Buckle


Golf belts don’t have to be worn on the green. Incorporate this classic golf belt into your daily wear this season and add a bit of flair to your palette. It’s decorated with the khaki plaid made popular by Burberry, yet without the unsettling price tag. When it’s seasonably right again, sport this baby and put proudly each time.

khaki plaid Golf Belt with Buckle Courtesy of Amazon


19. ToBeInStyle Pack of Three Loose Tartan Plaid Boxers


No one ever said that one had to wear a trend on the outside, did they? Aside from the fact that this is a great deal for boxers, you get to wear three different plaids.

ToBeInStyle Pack of Three Loose Tartan Plaid Boxers Courtesy of Amazon


20. L.L.Bean Mad Bomber Hat


As the temperatures begin to drop, protect that noggin with a hat that’ll trap in the heat. Rock this bomber hat from winter to fall and make it an outfit staple. Its fluffy interior is incredibly warming and the warm red plaid exterior makes it one of our favorite plaid picks listed.

L.L.Bean Mad Bomber Hat Courtesy of L.L.Bean


21. L.L.Bean Scotch Plaid Flannel Hooded Pullover


L.L.Bean’s been doing it like no other for years on end, so don’t be shocked that we’re listing them here yet again. As you can see by this plaid hoodie it’s obvious that this shirt was made with comfort in mind. It’s the perfect layer you never knew you needed and has a drawstring hood, loose cuffs and waistband and a quarter-button design. It’s easy to layer over a tee or under a denim jacket. For lounging in front of the TV, you might want to wear this with a cozy pair of sweatpants.

L.L.Bean Scotch Plaid Flannel Hooded Pullover Courtesy of L.L.Bean


22. Paisley & Gray Slim Fit Crew Neck Sweater


Who doesn’t love a cozy sweater? This wild one takes the plaid look to an entirely new level by looking more like an NYC subway station mosaic than anything else. This sweater is quite modern in its approach and will flair up your style a bit this winter — even if you think it might be a little out of your comfort zone.

Paisley & Gray Slim Fit Crew Neck Sweater Courtesy of Men's Wearhouse


23. Love Lakeside Cashmere Feel Plaid Scarf


Everyone needs a scarf when the wind blows and the snow is attempting to slink down the back of your neck. Why not wrap up in a cheerful plaid scarf? Not crazy about red plaid, well Love Lakeside has 17 other plaid combos that might tickle your fancy.

Love Lakeside Cashmere Feel Plaid Scarf Courtesy of Amazon


24. River Island Suit Jacket


A blazer is one of menswear’s big-ticket items. But, in this case, the ticket is quite small. For just $50, you can snag this gorgeous men’s plaid blazer from River Island and look dapper no matter what the day calls for. A blazer like this one will never become outdated because it’s styled so eloquently that it will always look fresh and fashion-forward.

River Island Men's Plaid Suit Jacket Courtesy of ASOS


25. Vans Tartan Authentic Sneaker


Skate brand Vans makes iconic sneakers. They’re constantly reinventing their footwear while still staying true to their roots. For fall, they’re using their classic low-top silhouette and adding some tartan flair to it. The pink and black plaid’s highlighted black laces and contrasting trim on the sides.

Vans Tartan Authentic Sneaker Courtesy of Vans


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