At a recent Facebook "town hall" Mark Zuckerberg fielded the question: Why do you wear the same clothes every day? His answer had to do with a tendency towards "decision fatigue" and how he wants, instead, to free his mind up to think about nothing but the company. (How far behind can diapers be when applying this logic?) Why do tech moguls like Zuckerberg and Jobs feel they are so different from say, Lloyd Blankfein, who could never justify wearing the same thing every single day? What Zuckerberg is describing is not a problem specific to tech CEOs. High powered, high functioning people at large don't have time to think about what they are going to wear, but most are not so insensate that they resort to a uniform.
There is an answer out there and it is NOT Black V Club. (There are myriad problems with this idea, not the least of which is that the name suggests a club for those with a certain common but specific fetish.) The answer is simple: HIRE A STYLIST! We do all the heavy lifting so, in the end, all you are doing is choosing an image of a complete outfit from your look book. It may not be as simple as wearing a black v-neck t shirt each and every day but at least you won't be mistaken for a homeless person.