Truth: men like gambling. We might not all know that you don’t split tens or be able to tell you the odds of completing your four card flush on the turn or river (19%) – but we still love it. These shoes are kind of like that – part fun, part serious business – without the wicked withdrawal symptoms. Something about a classic pair of shuttlecock sneakers re-envisioned by Converse just doesn’t seem like gambling – it’s just winning. These Converse Jack Purcell Brogue Leather kicks are case in point. They’re basically a pairing of a classic Purcell sneaker and a wingtip with just enough leather and some laces to make a point, without feeling like you’re bound by a dominatrix. You get to be as comfortable as ever while still rocking business class. For $85 you might as well go for brogue.