Dear Tell All: I got a new job last fall and am just starting to feel like I know what I’m doing. For six months I more or less faked it, projecting confidence while secretly struggling to master new skills. One reason the act worked, I think, is that I looked the part of an impressive employee. I invested in expensive suits, shirts and ties, and I polished my shoes daily.
I felt slightly uncomfortable in this new wardrobe, and it didn’t help that almost everyone in my workplace dresses casually. You almost never see men in ties or dress shoes. There is one notable exception, however: the boss. He always looks impeccable in stylish suits and pressed shirts. I’ve spent the whole year trying to impress this guy with both my wardrobe and my work, and I’m finally making headway with the latter.
So here’s my question. Now it’s summer, when my male co-workers are coming to the office in Hawaiian shirts and running shoes. Can I finally dress down too? I’m more and more uncomfortable in my suit, and I feel silly wearing it in the blazing heat. The problem is that the boss continues wearing his own suit. To me it looks like he’s implicitly setting the dress code, even though I’m the only guy who’s following it.
I don’t want to jeopardize my relationship with my supervisor just when it’s getting onto solid ground.
Sharp Dressed Man
Dear Sharp Dressed Man: My guess is that your wardrobe doesn’t matter to anyone in your workplace. The boss obviously isn’t setting a dress code because no one else is following his lead. If the guys in running shoes get to keep their jobs, you can surely keep yours without wearing a suit.
It sounds like you’re impressing your new supervisor in the way that really matters: by doing good work. In those first anxious months, I suspect that your dressy clothes were more important to you than they were to him. They bolstered your confidence when you felt like an impostor.
Plus, in situations like this, it’s always helpful to think about what you want to do rather than what someone else wants you to. And it’s clear that what you want to do is dress more casually. Maxwell Street Days is sure to have some good deals on Hawaiian shirts.
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