Pinstripe trousers have a reputation for being difficult, and most men treat them accordingly, leaving them to the suit wardrobe and nothing else. That’s the wrong call. Worn separately, a well cut pinstripe trouser is one of the more interesting things you can put on from the waist down. The stripe adds visual structure without shouting about it, and the right pair works harder than most men expect: with a plain knit, a white shirt, a clean leather shoe. The key is fit and stripe weight. A stripe that’s too bold reads fancy dress. Too close to the base cloth and you lose the point entirely. We’ve been looking specifically at trousers that sit correctly at the waist without needing a belt to hold them there, and that have enough cloth quality to drape rather than cling. These are the pinstripes that belong outside the boardroom as much as in it.