I have the advantage of being male and being a land surveyor in an engineering office. All my nicely dressed cubicle dwelling coworkers are used to seeing me show up in boots wearing wrinkled clothes and carrying a pile of winter gear while sporting a ridiculous hat-head hairdo. In addition to looking rather scruffy, I find that having the surly demeanor of one used to field work in DC's less than affluent neighborhoods pretty much stifles any unwanted commentary on how I look. Image is everything.
525EXC, 640 Enduro, XT200