When I first saw this image, we were asked to write down key words or phrases that you instinctively think about the character, based on this picture only.
Here are all of the words I came up with: old, scraggy, beard, looks homeless, only one outfit, beggar - possibly sells the big issue?, lives in a homeless hostel, perhaps a squatter, he doesn't look dirty... maybe the hostel has cleaning supplies, doesn't care what people think, he's wearing all the clothes he owns, smokes - money from the streets (smoking also means he doesn't have to eat as much - less money spent on food), he has confidence (in his stance), he's wearing a coat because it's cold (people around him are wearing coats), patched and turned-up trousers, had them for years? no wife or kids.
After being shown this picture of the same man on a day to day basis, and being told he works for Ralph Lauren in New York, I felt like I had stereotyped him to the maximum! He was simply at work on his cigarette break in the previous image, he likes that style of clothing so that's the way he dresses.
Images from The Satorialist.