our new hire dresses too casually for client meetings

A reader writes:

I work at a small start-up with about 15 people. We all work remotely. We recently hired a new employee for my team, and he is probably the youngest person in the company. We serve a pretty conservative field in terms of dress, expectations, formality — think along the lines of investment banking, law, or accounting. In internal Zoom meetings, our team wears whatever — sweatshirts, ball caps, athleisure, anything goes really. Externally, when meeting with our industry, we usually take it up just a notch; some people wear a sweater or a nice top, others stay bit more casual but would wear maybe a plain t-shirt with no writing on it, and generally appear neat. (We work with a lot of high-powered folks externally.) We do not have any sort of “dress code” and like most start-ups we don’t have a lot of rules in general.

This new employee wears a sweatshirt with writing on it and a baseball cap for every external meeting. It’s a little disconcerting! But it’s such a delicate topic. Should I say anything or just let them be themselves?

I answer this question — and two others — over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

Other questions I’m answering there today include:

• When you’re asked to hire the CEO’s girlfriend
• Lunch meetings when I can’t eat

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