I've finally acquired what might be described as a work wardrobe. Amusingly, after going through nearly a dozen stores (with Dangerfox, whose eyes lit up when I told him there was nothing wrong with wanting to "play dress-up" with his girlfriend as a canvas, and is dogged in his pursuit of my perfect hat) I ended up buying everything except the shoes from the Gap. I would have been utterly incapable of spending that much time looking for clothes a few years ago. My interest (or perhaps tolerance) for fashion has slowly been increasing for the past year or so, and it's been helped along by a rather silly realization: Fashion is built on the same principles as a CCG.
A new set comes out every so often, full of reprints and variations on old ideas as well as entirely new features. Every set focuses on a different aspect of the whole possibility space for the enterprise. If you want a very specific piece, you need to be willing to spend a lot of time shopping or spend a lot of money (and often, spending a lot of time shopping turns into spending a lot of money), and you might even have to wait until a certain style comes back into fashion if it's really unusual.
You'll need to update your collection periodically to remain current, but if you don't, that can be a statement in itself. Some people just look to the trend-setters for the "optimal builds," while others use their collections to build unique combinations that showcase their personal creativity. Others just want to be as shiny as possible. Kids tend to get into it when they're 10-13, and what they do with it tends to horrify their elders and embarrass themselves when they get older.