It used to be that a boy's biggest fashion decision was which color Toughskins he wanted, or whether he could get away with parachute pants at church. Tommy Hilfiger, Polo, FUBU and Nike rule their worlds. Pants must be baggy and long like the gear of their older siblings and contemporary idols. It's got to be at least a little bit baggy for me to wear it. Vests, as sweaters or jackets, are sanctioned, as are overalls.
Athletic garb is a solid winner, too.
Kids put a premium on replica jerseys and warm-ups, but really, anything with a Nike, Adidas, Reebok or Fila logo will do. Just enough details to satisfy the status quotient but not enough to offend the masses. Also in gray, it's heavy enough for a trip to the playground on a chilly day, but not so warm it can't be worn inside. Then again, if he's showing such telltale signs of good taste, give Junior what he wants. Forget Osh Kosh B'Gosh and tacky print turtlenecks.