The cuff on a pair of shorts is doing more work than most men give it credit for. Done right, it adds weight to the hem, gives the leg a clean termination point, and signals that some thought went into the cut rather than just the fabric choice. Done badly, it looks fussy or worse, like the shorts were simply too long and folded up out of necessity. We’ve been looking specifically at the shorts where the cuff feels intentional, proportioned correctly for the inseam length, and pressed or constructed in a way that holds through a full day rather than collapsing by noon. The inseam matters here too. We’re not interested in anything that hits mid thigh or lower than the knee. The sweet spot sits just above it, and the cuff frames that length exactly right. These are the shorts that look considered without looking like you tried too hard to look considered.