It would be nice to think that you can dress however you want, go where ever you want, and be left alone. It just isn't so. Not here in mostly white suburban Glastonbury, not in mostly black and Latino Hartford, and not in Sanford Florida.
Let me give you an example. I'm a friendly guy; I apparently look friendly enough and radiate this aura of trustworthiness so that people have always stopped me and asked for directions -- black, white, hispanic -- didn't matter. Then I got a buzzcut (#2 on the sides, cut really short on top). I have noticed that, now as a walk down the street about 1 in 4 people of color give me the hairy eyeball. Just by cutting my hair short I have gone from being Mr. Trustworthy and approachable, to a guy who apparently looks like an agent of THE MAN to some blacks and Latinos.
Here's my point: any young man, wearing a hoodie, with his face obscured by the hood looks like a hoodlum. Period, full stop. I see a couple white boys in Glastonbury with their hoodies on and hoods up slouching along the sidewalk and I immediately feel that prickle of raised alertness and suspicion. White boys, in Glastonbury. Now make it a young black man, in a hoodie, in the dark, in a neighborhood that has had a rash of break-ins perpetrated by young black men.
Here's my advice, to all young people, but especially young black men: LOOSE THE HOOD. Criminals, since the dawn of time, have covered their faces. Don't look like a criminal. If your head is cold, or wet, or you're having a bad hair day, wear a hat. A baseball cap or a fedora or a pork pie hat, not a knit cap pulled down low over your eyes.
I would love to go to work in jeans and a t-shirt every day. Can't do it. I'd get my head handed to me. My sister once got tailed by staff all through an expensive "gift shoppe" because she walked in wearing her landscaper work clothes. They thought she was going to shoplift. Trayvon Martin got tailed by a nervous citizen watch volunteer because he looked like he didn't fit the model of an honest resident, but instead looked like he fit the model of a criminal.
In an ideal world you could wear whatever you wanted where ever you wanted and it would be OK. This isn't an ideal world. Loose the hood - don't loose your life.