The risks with socio-economic profiling are obvious.
You could be wrong. The person you assume to be poor might not be.
But I have developed a rule. If I am in downtown Spokane, I do not take for granted that someone wearing a Miami Dolphins hat or University of Michigan jacket has any connection to or interest in that team or school.
As I have learned partly from starting conversations that quickly went nowhere, a fair amount of the apparel in that category gets passed along through clothing-donations programs.
And saying "Go Blue!" to some guy standing in front of the bus station is apt to produce a mystified look.