Reader Question: Stylish Shoes for a Casual Workplace?

You came to the right place (sorry, I’ve always wanted to say that).

You said your co-workers are usually in work boots and sneakers, so I’m guessing this is a jeans-to-khakis-when-you’re-feeling-fancy kind of place. Yes? Cool.

It sounds like you lean more towards the chino end of this dress code continuum, and I definitely want to encourage that. That said, there’s dressing up, and then there’s being that guy that wears wingtips and a pocket watch hanging off a chain in his waistcoat just to make a point about how much fancier he is than his co-workers, whom he calls “hooligans” with a fake British accent for no reason. Nobody likes that guy.

Enter: the chukka boot. This humble shoe is my go-to for guys when they want to look more put together but don’t necessarily want to upgrade to the next level of dressiness with the rest of their wardrobe. Chukka boots look good with dark jeans, cords, khakis…any straight leg pant that’s already in your closet.

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Oh, and chicks love ‘em.

I know I do. A guy in chukka boots looks put together in a way that makes us assume you know what you’re doing in parts of your life that have nothing to do with your wardrobe. Assumptions like:

Mmm, I bet that guy regularly contributes to a 401(k).

Or: He probably takes care of the check on a first date while you’re in the bathroom.

And even: I bet if I went back to his place there wouldn’t be empty ramen packets in the trash and underwear on the floor. He might even have wine glasses made of actual glass.

In other words, not so dressy that we’re intimidated by your trendiness, but enough that we feel confident about your competency in being a grown man who knows when it’s time to upgrade from his beat-up sneakers.