Jack Erwin is a New York-based shoe startup that has gathered a following with their reasonable prices for made-in-Portugal shoes and free returns.

While the name implies that these are your typical boat shoes, the styling certainly does not. Made from soft calfskin and nubuck leather (regular cow leather that has been sanded or buffeted to give it a velvet or suede-like appearance), the shoes are a significant upgrade to your typical boat shoe and will mold to your foot over time.

In fact, we hesitate to even call them boat shoes like Jack Erwin does. It seems to do the shoe a disservice to lump it in the same category. The leather colors, the matching stitching, the minimal design, and the low-profile sole all add up to an elevation of the classic boat shoe style.