Cycling shorts have had a strange decade in menswear. What started as pure athletic wear got picked up by streetwear, mishandled by fast fashion, and now sits in a place where most men either dismiss them entirely or wear them badly. The problem is almost always fit and fabric. Too loose and they look cheap. Too shiny and they belong in a peloton. The ones worth wearing hit a specific middle ground where compression is present but not aggressive, the length sits at the right point on the thigh, and the material reads as considered rather than athletic by accident. We’ve been particularly interested in options that work with an oversized tee or a longer shirt, since that combination is doing real work right now for warm weather dressing. A good pair of cycling shorts resolves a specific seasonal problem that a lot of men haven’t found a satisfying answer to yet. These are the ones that actually solve it.