The Complete and Total Loser is physically deformed. Not that all losers are deformed or that all deformed people are losers. There are many one-armed people with good careers and loving spouses. (The Loser has both arms. His deformity is not interesting or touching. It's the kind that causes ill-mannered school children to laugh and shout to alert their friends.) But deformities can nudge personalities. The confident deformed man will swagger a little less; the shy one may withdraw from social settings completely. Spurned and ridiculed, he will try to connect with others in his youth only to surrender and make attempts fitfully into middle age. When they fail, he retreats into a world of his making that makes sense to only him.When you look different, you dress in ways to hide your deformity and draw as little attention to yourself as possible. For the Loser this means black pants, always, after learning during his travels in developing countries that they make his deformity, which is below the waist, slightly less striking from a distance. For shirts he wears long-sleeved button downs, solid colors usually.
Undergarments are a T-shirt and briefs. Although when in college his older brother told him that the two necessities for getting laid were Brooks Brothers boxers and a car, he's more comfortable in briefs and has no hope of anyone save emergency room workers seeing him depanted.
No jewelry. Sweaters are out; he fears they make him look weak and effeminate.