There is a version of this category that goes very wrong very fast. Novelty prints. Thin cotton that bags out after two washes. Waistbands that roll. We have all owned a pair like that and we have all quietly binned them. What we are after here is the opposite. A classic boxer short in a proper woven cotton, cut with enough room to be comfortable without looking like you borrowed them from someone larger. The kind that still looks respectable when you are getting changed at the gym or at a friend’s place for a wedding morning. It matters more than most men admit. We have been looking specifically at options that use quality poplin or oxford weave cotton, that have a proper fly and a waistband that stays where it is put. Simple patterns, stripes, small checks, plain colours. Nothing that is trying to make a statement. These are the ones that just quietly get everything right.