How to Beat Your Boss (And Still Let Him Win)

By Tanner Cormier

You can't beat your boss at golf, but you can look better losing than he does winning.

It may still be March, but spring is in full swing and the Masters Tournament is less than two weeks away. With fairways growing and greens, er… greening, golf fever is about to spread.

Unfortunately for you, that means golfing with the boss. It’s an unwritten rule that in order to properly navigate the employee-boss golf match, the underling must always lose. How you go about it is up to you, but the point is: if you win, you lose. Your boss’s ego is as delicate as it is inflated; tread too heavily and you could find yourself in a precarious power struggle back at the office. Solution: outsmart conventional wisdom by ignoring your par all together and parlay your smartly put-together golf attire into a winning stroke.

Golf, being a fairly traditional sport, can be tricky to dress for. But a quick look at any tour coverage tells us one thing: the pros are golfing in style. The key is to keep the cut classic while letting your style show in colors and prints.  Shirts come in every color; but the trend can be staid and boring. Going for brightly colored pants or shorts (if your course allows shorts) is the right kind of risk to take. These faded red Hartford chino shorts ($194) may take confidence to pull off, but they’ll project it too. And the key to wearing colors is to keep it to one piece, letting it act as an accent in an otherwise neutral or classic color pallet. A white Fred Perry Twin Tipped polo ($69) straddles the line between hip and classic, keeping the look crisp.

There’s no way around the fact that most golf shoes are ugly. Even the biggest names in golf apparel offer few options for the more style-conscious golfer. But there is hope in these Travis Mathew shoes ($70). They could easily be worn on the street, but the rubber pegged sole is designed to give you traction on the course.  And lastly, cap off your look with something functional: a straw fedora. Though they never really left street style, fedoras have made a resurgence for the summer, sported by the likes of Pharrell Williams (who’s been dubbed the Best Dressed Man in the World). The Brixton Castor ($40) in brown is structured enough to fit the golf profile but brings a more casual feel, like a breath of fresh air on the links.


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