That doesn't mean, however, that low-profile moccasin-style leather shoes shouldn't be worn at all. In fact, there are a number of styles that we recommend.
Let's add one more to that list: Jack Erwin's new Cooper boat shoe. 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.
The shape is more reminiscent of an elegant loafer than a sporty boat shoe, since Jack Erwin elected to use a loafer last (the wooden piece used to mold the shoe) instead of a typical boat shoe one.
If the issue with regular boat shoes are that they look more suited to yachting than running errands in the city, these shoes completely solve that issue.
Unfortunately, all of these upgrades come at a price. The Cooper line sells for $125 and comes in caramel, slate, and navy. This price point raises the shoes into a more competitive shoe style category, along with penny loafers and other loafer-style shoes. Sperry's start at $95, but can be had even more cheaply than that on Amazon.
It might be hard to convince guys to invest in a nicer pair of boat shoes, especially when the whole point of them is that they are made to be bought semi-cheaply, worn into dust, and then tossed aside and replaced.