Is It Wrong to Wear Expensive Designer Clothes to a New Job? Vanessa Friedman, fashion director of The New York Times, takes reader questions. Credit...Stigur Már Karlsson/Heimsmyndir April 2, 2021 I am a young professional starting my first major job at a large company. I was fortunate, in my early 20s, to invest in nice designer pieces. Most of the clothing is inconspicuous, but the shoes, and especially the purses, are obviously designer goods. I don’t want to send the wrong message to my colleagues or bosses, especially as someone low in the pecking order. But I already have this nice stuff that I’d like to get use out of. Plus, I’d have to spend even more money to buy items I really don’t need if I can’t wear the ones I already have. What should I do? — Elizabeth, Chicago