The Best Men’s Plaid Shirts for Fall and Winter

The Best Men’s Plaid Shirts for Fall and Winter

It's a plaid, plaid, plaid, plaid world
best men's plaid shirts 2023

By Megan Collins | Last Updated: Nov 1 2023 | 6 min read

Forget the changing color of the leaves on the trees, or the sudden appearance of pumpkins on every porch you pass. How do you really know fall has arrived? The return of plaid in men’s wardrobes, and lots of it.

But here’s the thing. It’s easy to default to “sloppy” or put more diplomatically “cozy” outfits when wearing plaid, but don’t box this admittedly boxy pattern in!

Plaid can go with you back to the office, or layered into an uber-stylish date night look. Most important to remember? Plaid doesn’t automatically mean flannel.

The short answer to the question, “Is there a difference between plaid and flannel?” Is Yes.

The slightly longer answer? Flannel is a type of fabric, while plaid is a pattern. Flannel is what a soft plaid shirt is often made of, but not always. A plaid shirt can be cotton, wool, or another material.

Bottom line? Once the temperature hits “light jacket” on the thermometer, it’s time to sport as many iterations of this autumn staple as you can fit in your closet.

Below, check out the best men’s plaid shirts in 2023:

Best casual plaid shirt on a budget – American Eagle, $50

SG SAYS: Are we supposed to call American Eagle just ‘AE’ now? I honestly cannot keep up.

Anyway, this shirt is billed as “super soft flannel,” and hoo boy does it deliver. And they’ve got so many colorways; you could wear one every day of the week, basically now through February.

Not that you should. Just that, you know, you could.

Best casual plaid shirt splurge – Corridor, $195

SG SAYS: This bright, multi-colored plaid shirt from Corridor feels like a welcome burst of sunlight on a dreary day.

Wear it on the mornings before Daylight Savings hit…you know, the ones where you have to leave the house before the sun is even up.

Pair it with jeans, trousers,

Best plaid dress shirt – Hamilton x Todd Snyder, $215

SG SAYS: See, plaid doesn’t equal flannel! This Hamilton x Todd Snyder collab is made of Egyptian cotton for a beautifully smooth and lightweight feel.

The color combination feels work-appropriate, and gives off an ironically normcore vibe, which I love. Definitely strikes a more stylish tone than your average business casual plaid.

Bottom line? Plaids don’t just come in itchy, burly lumberjack wool and flannel. A cotton dress shirt in the pattern gives off a crisp appearance and looks right at home with a full suit (check out exhibit A from Jason Sudeikis) or under a sport coat.

Best plaid shirt jacket (aka shacket): Wax London, $215

SG SAYS: Call it a work shirt, overshirt, or shacket. Just be sure to call it up in your wardrobe rotation this fall and winter.

This overshirt from Wax London can be worn open over a lighter layer like a t-shirt or cotton sweater. It looks good with everything from jeans and casual khaki pants to a more sturdy carpenter pant and even dress pants.

You can also button it all the way up to let the overshirt be the statement piece of your outfit.

3 tips for wearing men’s plaid button-down shirts this fall and winter

1) Dress it up or down

source: @acutestyle

I’ve worn my favorite plaid shirts over ripped jeans and dresses and everything in between.

No, I don’t expect you to wear yours the same way…what I’m saying is, plaid is versatile!

Guys have the opportunity to dress plaid up for work, adding some always-appreciated visual interest to an otherwise staid casual corporate uniform. And yes, you can wear plaid with jeans or chinos on the weekend.

Consider plaid to be cold weather’s cousin to gingham.

It’s just such a workhorse—what else in your wardrobe goes from hay rides to the office and onto date night so seamlessly?

2) Consider all the colors in your plaid for pairing

Bryce Harper in Deion Sanders t-shirt
Bryce Harper repping Deion Sanders under his plaid shacket | source: @phillies

Depending on the plaid shirt or shirt jacket that you’re wearing, you may find three, four, or more distinctive colors to riff off of in your outfit.

Maybe a predominantly green plaid has a stripe of yellow that you can play off of in a sport coat’s pocket square. Or a red/purple/brown shirt that goes perfectly with an orange pin dot knit tie.

How to know you’re getting it right? Just keep it in the same color family.

Cool colors go with cool colors; warm, autumnal colors are happiest with each other—and you’re good to go. Check out how creative—yet totally pulled together—Andy Cohen looks here.

3) Aim for flattering, not frumpy

Jake Woolf in plaid shirt
image: @jakewoolf

What I’ve learned in my plaid-ventures (eh?) is to create a look that says “I woke up like this” Beyonce-voice vibe with your plaid.

Opt for shirts that skim your torso, not billow out from it.

When wearing jeans, go with a French tuck, so just the front of the shirt into where the button closes for a look that’s breezy but still figure-conscious.

Remember, you’re going for good-looking, not grunge.

Of course, there’s nothing wrong with leaving your flaps flying on the weekends, but to be sure you’re pulling off your plaid properly from Monday to Friday, keep those tails tucked.

Want more style support? Check out Team SG’s favorite light jackets for fall.

I started Style Girlfriend to help guys look, feel, and act their best.