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Here 5 Things I Would Never Wear After Working for Rich People I learned to never wear after working for wealthy people in New York City. Number one is long nails. They get really dirty, and they're very noticeable as they grow out. Number two is wrinkled clothing. No matter the price, the fastest way to look cheap is to not iron your clothing. Next is an asymmetrical top. My boss hated these. She always told me they're really distracting, they never fit right, and it just looks like someone sewed it wrong. Next is printed shorts or shirts. In my boss's opinion, prints always look better on shoes or bags. Unless you're wearing a dress. For example. If you have a printed shirt, there's not an even distribution of the print in your outfit, whereas if you're wearing a dress it looks a bit more chic. No. 5 is clothing that's a little too small. In my boss's opinion, fit was everything, so even when she was fluctuating sizes, she would always have jeans that were bigger or smaller based on where she was at in life. And then No. 5 is clothing with metal accents. Unless the hardware is really expensive, Good quality***** which often times even the most expensive brands are not, it dulls out quickly. This can really cheapen your look.