Oak Street Bootmakers tends to stick to the classics, and no line based around classic designs is doing it right without a blucher moc. A staple of Ivy style and beyond, and championed by everyone President Kennedy to Ned Flanders, it’s a shoe as comfy as a loafer with laces added to enable more vigorous activities. The famous images of JFK sailing in them come to mind.

Handcrafted in the US, this pair is done in natural leather that’s been given the Chromexcel treatment by the fine folks at the Horween. The key to the comfort of in this shoe is in the hand-stitched moccasin construction which wraps a single piece of leather under the footbed. By having that single layer of leather under the bottom of the front, the shoe truly molds to the foot quite easily and eventually feels more like a sock. Just part of the reason this style hasn’t ever fallen out of favor and is still relevant today.

On sale for $171.60 at Wilson & Willy’s