21 Can't-Fail Shirts You Should Wear to Every Event on Your Groaning Calendar (2024)

Throw it over a turtleneck, and you've got your wine-night-poetry-set look down pat.

The worst-kept secret when it comes to staying warm and looking, like, 50% hotter in the process? It's this guy right here.

Put them in a trance with a button-up that looks decidedly of-the-moment retro, not dated.

A denim shirt with a lil' extra weight so you can keep the Canadian tuxedo alive once winter hits.

That traditional Scottish tweed will add level of dimension and refinement to even the most chilled-out look.

How do you straddle the line of casual office garb while still looking put together enough to nail an impromptu presentation? This shirt, right here.

It's an eternal summer (at least in your head).

Cold weather and buttons are a disastrous combination. Zip up this guy when it's freezing out and give your digits a break.

You're the gift this season, so dress like one.

The thick-trimmed pockets and hem take this shirt from pencil-pushing professional to plain old professionally cool.

Exactly what you want in an overshirt, from a brand on the nexus of the nice, normal clothing movement.

Yes, the goes-with-everything white whale of button-ups you’ve been chasing your whole life is out there, and its name is the denim shirt.

On the eve of its 100th birthday, L.L.Bean’s legendary chamois shirt—the unofficial uniform of East Coast dads lugging the toolbox out of the garage to fix that leaky faucet, dammit—looks better than ever.

A thick wool overshirt is slickest way to stay comfortable this time of year, which is what casual is all about, right?

Brooks Brothers helped introduce the Platonic OCBD, originally designed to prevent shirt collars from flapping around on the polo pitch, to the American masses. After all this time, the centuries-old brand still sets the standard.

The London-based brand has been all about "relaxed elegance" since its inception in the late '70s, so you know you're in extremely good hands when it comes to any of its shirting selection.

If your idea of casual skews more “rooftop drinks” and less “park hangs”, a crisp poplin shirt will always serve you well.

Thom Browne's signature stripes might drum up the most buzz, but this cozy tartan shirt is a stellar example of what you get when the cheeky prepster takes on workwear.

Cut from organic cotton with the relaxed fit of your favorite striped button-up—and with the same inimitable polish.

Slightly heftier than chambray but way more laid-back than regular ol’ cotton, denim in any form should be your foolproof ace in the hole when it comes to casual dressing.

With a shirt this dynamic, your outfit will practically take care of itself (but if you're looking for a styling recommendation, tucking it into a loose pair of denim or some sturdy chinos is a great place to start).