Most men own shorts that belong on a beach and nowhere else. That’s fine for the beach. It’s a problem everywhere else summer asks something of you. A rooftop dinner, a weekend away somewhere with a bit of style to it, a lunch that’s too warm for trousers but too considered for whatever faded swimwear you’ve been holding onto since 2016. Tailored shorts solve this without making you feel overdressed or like you’re trying to look European. The key is in the cut and the fabric. Too long and they read as awkward. Too short and you’re in different territory entirely. The sweet spot sits just above the knee in a fabric with enough structure to hold a crease but enough weight to move properly in heat. Linen, cotton twill, a good wool blend for cooler evenings. We’ve pulled together the pairs that understand the assignment and wear well with a leather loafer or a clean white sneaker equally.