I hate the whole smart-casual look and I think a suit would be over the top. I also feel a bit embarrassed about coming in one day with a whole new wardrobe. What should I do?
A: Like a great many people, you're quite self-conscious - particularly about clothes. (When I was about 10, I absolutely refused to wear new shoes, convinced that the moment I ventured out in them the whole world would point at me, convulsed with mocking laughter.) You've also found a style (or lack of one) that suits your attitude to life and work and you're understandably reluctant to abandon it. Well, two things. First, other people aren't anything like as conscious as you are of how you look. And second, you don't have to do everything at once.
You don't have to stage some dramatic transformation scene, leaving on Monday night as a scruff and turning up Tuesday morning in white tie and tails. That might attract more attention than you'd enjoy. Just gradually upgrade your jeans, your shoes, your T-shirts - but do so one by one. After a week or so, try out a plain, unstructured jacket. You'll get the odd comment, obviously; but they'll be mostly approving, and even the teasing ones will be affectionate. And a lot of people, of course, simply won't notice that anything is different.
Jeremy Bullmore is a former creative director and chairman of J Walter Thompson London. His book, Another Bad Day at the Office, is published by Penguin at £6.99. Address your problem to Jeremy Bullmore at: email@example.com. Regrettably, no correspondence can be entered into.