Why does fit matter?
Because failure rates follow fit. In a study of 436 men, those reporting ill-fitting condoms had 2.6 times the odds of breakage and 2.7 times the odds of slippage, and both partners reported less pleasure (Crosby et al. 2010). Too wide and it slips, which is a contraception failure, not a wardrobe issue. Too narrow and it hurts, tears more easily, and tends to come off mid-act, which amounts to the same failure. The fix costs nothing: read the number on the box.
Full citations for the sizing standard and the fit research are on the method and sources page.