This is a great goal. I was able to achieve a similar goal once I began working from home - e.g. no longer needed the uniform to show off in the corp world. That said, I already had plenty of simple, high quality weekend workout wear with the addition of some very comfortable Gap long and Short Sleeve Shirts on sale and the occasional replenishment of levis that last my wife and I for almost ever - especially if you line dry - we are down to almost zero except for cotton sox and unders that we now get on amazon on the cheap. If I had to continue to go into the office, I would simply update my collard shirts, more stylish T's a couple times a year, on sale. Working from home has been a huge wealth builder for anyone just starting to do it as you don't need those clothes, no more overpriced cosmetics for my wife for which she now realizes she never needed in the first place, no more cocktail hour with people we don't really like, no more daily java at starbucks or lunch at wherever, no more commuting costs. I think Steve Jobs adopted the almost all black all the time and we have done the pretty much the same. Jeans, Yoga or Workout Wear w/Black/Gray T's and not too much else. Have not purchased shoes since 2008 since we are no longer slaves to silly fashion or the social norms. People may assume that we are poor slobs but the beauty in that is that we don't really care and we are FI because of it. have fun!