20 Best Polo Shirts For Men 2020

From first grade to twelfth I went to a school that stipulated I wear some sort of collared shirt at all times. Naturally, I daydreamed of tees. The polo became my arch nemesis. A lackluster substitute for the T-shirt, its more casual cousin, the polo represented—at least in my mind—the worst type of tyranny. Even then, not being able to wear whatever I wanted, whenever I wanted, bothered me to no end. (Was I mortifyingly self-centered and otherwise ignorant of the actual, very real issues kids my age were dealing with around the world, let alone within my own school? Dude, I was, like, 15. No shit. I was a fucking moron.)

As soon as I graduate I’m never wearing one of these things again, I remember thinking to myself. Sure, it’s not like the polo was my only option. But button-downs often felt comically dressy for a middle schooler with a build you might very generously dub “slim-thick” today, and in high school the last thing I wanted to do was spend time cheffing up a grown-ass fit each morning when I could be catching up on sleep. Polos became a go-to, the easy, collared, T-shirt alternative I loved to hate. (Suffice to say, the fits I could’ve—should’ve!—gotten off throughout those years still haunt me to this day.)

And then a funny thing happened. A few months ago, the polo—long considered a symbol of ultra-privileged WASPdom and now fending off serious co-option attempts from the worst of the alt-right—suddenly started looking like one of the most democratic pieces of clothing a guy could own.

Because all those perceived cons I was too stubborn to appreciate at the time make the polo (sighs deeply) a perfect shirt for this particular moment. It’s comfortable and flattering. It’s easy to style and effortlessly frames your face, even despite the unforgiving lighting and odd angles that are now WFH norms. And, crucially, it somehow still manages to straddle the line between helping you look appropriately dressed-up and not making you feel like you’re the one dude who came through in a suit and tie when the invite called for “creative beach casual.”

In other words, my sweet, sweet prince: It wasn’t you, it was me. Any chance you’re ready to give it another shot? I’m different now. I promise.