The side zip boot has one job the Chelsea boot cannot always do, which is stay on your foot properly when your ankle sits on the narrower side. A Chelsea relies entirely on elastic tension and if that tension is not calibrated for your foot, you spend the day fighting a boot that slips at the heel or pinches at the instep. The side zip solves that. You get the clean silhouette, you get the versatility across smart and casual, and you get a fit you can actually dial in. Where most men go wrong is buying a pair that looks good on a website and then discovering the zip hardware digs in after an hour of walking. We have been specifically looking for boots where the zip sits flush, the lining is properly finished, and the last is shaped for wear rather than display. Good looking boots that you can actually wear all day. That is a shorter list than it should be.