Even if you think of checks, plaid, or gingham as being the "it" prints of the moment, the truth is that they've always been a go-to for guys. Love it or leave it, plaids and checks are here to stay. With such an array of style classifications—indie, prep, backwoods lumberjack, exec—some form of plaid or check will always be in style. Like most trends, you'll see versions of the classic sway from one end of the spectrum to another.
Not being a disciple to trends, I tend to think any of the above are fair game, given your own aesthetic. Don't buy something just because you're seeing it on everyone else, and be sure to accessorize to fit your style. Personally, I prefer to pair plaid shirts and a classic, slim jean with a bow tie or straight tie, depending on that day's schedule. I also like the juxtaposition of plaids or checks with a coordinating, but not quite matching, color—say, a Kelly green and ivory check with a pair of slim, navy chinos. Purchasing plaids and checks is effortless because the stores are full of them at the moment; I'd recommend brands like Ben Sherman, J.Crew, Gucci, John Varvatos, N.S.F., or vintage.
Finally, remember to hang on to those checks and plaids: I promise you'll find yourself wearing that same pattern 10 years from now with the same classic appeal as the season you bought it.
Jacob Laws is a senior designer at CURE Design Group.