I know I am late by a couple of years, but better so than never. I bought The Sartorialist book. Need I say I love it? For several reasons nonetheless. First, despite the fact that these photos were taken prior to 2009, the people in them would still be considered stylish today. Not everything they are wearing is even designer, and if it were you wouldn't know about it because Scott doesn't post labels, their style is timeless. As he puts in his introduction "I like people to draw their own conclusions, to find their own inspiration without the influence of a guiding hand," meaning he doesn't need to post a description about every single outfit because different people may notice two completely different things about an outfit.
I also loved the honesty of this book, which is portrayed in the photos and the short blurbs of his thoughts and experiences in shooting a certain person. I wish I could share them all with you, but I think it's better you get the book yourself! You can find it discounted online, as I did. How can you say no?
I think most of us are like stylish hermit crabs: we change our outershell to camouflage out way into certain social positions. We 'dress the part'. When you accept this idea, fashion/people watching becomes less judgmental and more about being 'visually greedy'. It comes less about what that person is wearing and more about what the elements of the look can mean to your own personal style. 'Visual greed' is one of the reasons I don't usually put the name of the person or labels that they are wearing on my blog - they simply don't matter to me. For instance, this gentleman was shot outside a recent Ralph Lauren fashion show. I know he works for Ralph and I know that Ralph 'encourages' employees to dress in a certain 'Ralph Lauren-ish' manner. So is his look real personal style? I don't know and I won't judge him on that, but I will allow myself to be inspired by the concept of a Navy blazer with totally distressed jeans or crisp side-parted hair that always seems to look modern. In a way, being 'visually greedy' allows you to separate the personality from the 'look' and puts the pressure on you to figure out how to harness that stimulus instead of just grading other as 'pass' or 'fail'.
Pictures copyright to Scott Schuman, duh.