Chicagos are more iconic, objectively speaking. I personally prefer the breds. Chicagos are worth more money. Neither are that cool though imo. If you love Michael Jordan than it's an incredible feeling to have his first signature shoe. Otherwise I would suggest some dunks, air forces, or blazers, as those are often less than $100 and look very similar. The comfort on Jordan 1s are below average as well. If you are under 20, meaning you weren't even born when MJ retired as a Bull, and these are a "must have" for you.. please check yourself as you have been PLAYED by marketing and hype. If you grew up watching the bulls, then I have nothing bad to say, and I respect it and the meaning.