Some of our readers have expressed concern about the liability of dressing too well?particularly better than one?s boss. Common wisdom says that if you dress better than your boss, you risk his/her ire or jealousy, so you should dress down. I agree, but only if your ambitions go no farther than being a subservient cubicle drone happy with a stagnant but secure job. But if you want to earn your boss?s job someday or one like it, kicking up your personal style is a guaranteed way to distinguish yourself from your rivals.
Sure, you might tick off your boss. Sure, your co-workers might call you a dandy or even a pretentious fop behind your back, but I?ll bet they will secretly admire you as they try to conceal their envy for your eye-catching cufflinks, crisp white dress shirt, and what Forbes.com called "One of Ten Shoes Every Man Should Own" – Toschi?s Berta.
I say: Don?t dress like the man you are; dress like the man you want to become.
Dressing well is a subtle but powerfully symbolic act of male aggression, but that?s what business is all about?cut-throat competition, balls and brashness, vigor, and survival. J.P. Morgan didn?t have a lot of friends. There was a reason for that. He didn?t want friends. He wanted big-money and all the status that accrues to a man of power. He never ever dressed down.
In our own time, you?ve never seen Donald Trump in a track suit. He?s always in a pricey suit and big phallic-y ties. He?s the Man. Or he thinks he?s The Man. Even though he might not be, he acts the part every day, every night, brushing off ridicule about his hair, his ego, and those God-awful gaudy ties as if they were merely so much lint on his lapel.
To win in business and in life one must not feel guilty about one?s prowess, strength, and talents. Naked ambition should not cause shame. Naked ambition should be clothed in the finest suits and accessories you can afford. Think of it as armor. Style is a gentle but powerful weapon for the man who insists on success. He?s not sitting around waiting for his ?big break.? He?ll make it happen himself, some way, somehow.
And if your boss doesn?t like it, then you?ve successfully exposed a weakness you can exploit. If he fires you, then you weren?t going anywhere in that firm anyway, so it?s best you find a work environment that appreciates your strengths rather than regards them as a threat. Just remember to tip your hat to your ex-boss as you head out the door on your way to greener pastures.