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I tend to dress down to the lower level of office policy. At a previous job, working a help desk, I got tired of business casual and started wearing jeans to work. No one objected (hell, we didn't interact with anybody face to face so it was no big deal) until my friend Kelly took things to a new low. She started wearing jeans, a white t-shirt and a red bandana on her head ... she looked like a cleaning lady. Casual is one thing but we were still working for a law firm and we received a memo shortly after that.