All black outfits has been a played out look for some time. One way to make it interesting is through use of texture and finish, neither of which are usd by these men. Doesn't help that none have particularly hip looking faces.
2. Has the hippest hair. Are sunglasses still hip? Sometimes yes, sometimes no.
3. Has the hippest clothes. Polo shirts or John Smedleys are much better than T-shirts under jackets.
1. I think is doing Charcoal Grey over Black which is far, far cooler than Black on Black. So he gets marks for that.
Mix them all up & you have The Hip.
Black John Smedley under a Charcoal Grey suit. Loose the sunglasses. Have interesting hair & look serious. Well... not serious, but look intent on something. Anything.
Be urbane & charming but pretend that something (anything) someone says hits on a raw nerve with you. Makes you look deep & multi-layered. Do lots of eye contact & quickly looking away stuff before you make your move. When looking away always look down (thoughtful) and not to one side (shifty). That's the way to do it.
T.
No, No, and No.