Shirts for work and shirts for play are not created equal.

Shirts for work and shirts for play are not created equal.

To avoid looking buttoned up in a button-down, we zeroed in on stylish, fashion-forward versions of the staple shirt. Pick one up to keep from looking like every other guy out there this summer.

In crisp black and white, this gingham will look cool this summer with the cuffs rolled to the elbow. The extra pocket makes it just different enough.

Dear Creatures, $96 at Tigertree

Short-sleeve button-ups have overcome - or, maybe, embraced - their pocket-protector stigma with the help of rolled cuffs, epaulettes and snaps instead of buttons. This navy-and-red plaid is the perfect example of the resurgence of nerd-chic, Brigade manager Larry Robertson said. "Any guy wearing this isn't a nerd."

APC, $130 at Brigade

A short-sleeve, (airbrushed) pink button-up? What makes it wearable over, say, a department-store version in the same shade is the fit, Milk Bar co-owner Eric Hayes said. "The thing that most designers are doing is shortening the hem up two-and-a-half inches. It's a huge difference. Most guys look kind of lost when their [standard-length] shirt is hanging out. These shirts are meant to be worn out."

Band of Outsiders, $220 at Milk Bar Boutique

It might not be plaid, but this button-up is far from plain: stitching details, a more fitted shape, buttoned pockets and a chest pocket that seamlessly blends in at the seam make this gray-blue shirt look fresh.

G-Star, $120 at Brigade

We're loving this energizing color combination. It's the ultimate wear-anywhere button-up, perfect for summer and beyond.

Ben Sherman, $89 at Tigertree