Most men treat sandals as an afterthought, grabbing whatever’s nearest when summer arrives and then wondering why the rest of the outfit falls apart below the ankle. Strappy sandals in particular have a reputation for looking borrowed from someone else’s wardrobe, which is fair when the construction is poor and the leather is thin enough to crack by August. The ones worth owning are different. Good strap placement, substantial footbed, leather that actually improves with wear rather than giving up after a fortnight. We’ve been looking specifically at styles that work with tailored shorts as well as something more relaxed, because the best sandal does both without asking you to overthink it. There is a real skill in making something this minimal feel considered rather than lazy. These selections manage it. If you’ve written off strappy sandals before, we’d suggest the problem was the sandal rather than the category.