I'm not a fashionista or anything, but I think it's more about finding your style and finding your fit within your style. Feeling good about your look is more important than it working for you in my opinion. The easiest upgrade with the most impact is generally tshirt to some other kind of top, but his looks are often a little more involved than top+bottom. He does have the traditional model aesthetic of tall and thin, but I think his tips and general style could be incorporated by anyone.