American shoemakers working with decent leather and old-school methods are few and far between. Out of Chicago, Oak Street Bootmakers is one of those makers and, seeing as their End of Season Sale just started, it’s high time to consider one of their pairs.
Handmade with Horween Chromexcel leather and crafted into classic styles like the trench boot, camp boot, and chukka, Oak Street’s work is entirely unburdened by excess threading and non-essential design elements. The boots are made by George Vlagos and his team in the same fashion as they were by Vlagos’s father, a master cobbler, decades before. Due to the quality of the leather used, pay keen attention to the sizing section on each product, as some recommend true-to-size fits and other going down a half-size due to the shoe conforming to your foot.

Trail Crazy Horse Trench Boot by Oak Street Bootmakers $426 $320

Snuff Suede Plain Toe Blucher by Oak Street Bootmakers $476 $309