"I’m using the term “rock” Converse not accidentally because here’s the deal you either pull it off and look hot doing it or you shouldn’t be wearing them in the first place – there’s no in-between, as a piece of a wardrobe Converse shoes have a strong identity and you should have one too.
That said, there are some tangible factors that can help you determine whether you should order a pair right now.
So here’s the deal:
Optimal age – <30. Exceptions of course are possible, but pretty much after 25 your image needs to consciously and clearly convey that you’re wearing them on purpose, deliberately and not because you’re still in denial that college is over.
Optimal look – edgy-casual. As mentioned earlier Converse has a strong identity as an item and is associated with being a rebel, the bad boy but in a chill, relaxed way (not the “badass-aggressive” type) – it’s an extremely attractive combination but it also means that when you add Converse to an outfit it will overwhelm and out-shadow other items that don’t have a strong identity like that. I.e. if you end up wearing them with a blazer, it won’t be a truly classy look any more.
In other words, if you’re a cool younger guy (or feel young at heart and are not afraid to show it), that doesn’t take things too seriously, enjoys life and is not afraid to do things his own way, nor do you need to appear professional/respectable in some dinner event – GO FOR IT!
On the other hand, if you can have a glass of wine and say something along the lines of “A wonderfully rich and complex nose of truffles, plums, tobacco and minerals with a touch of classic pencil-lead and leather. Stunning.” with a straight face and actually mean it, it’s probably best to skip this article. (Or prove me wrong!) "