Oak Street Bootmakers
Oak Street Bootmakers is a relatively new American shoe manufacturer founded by George Vlagos ("son of a cobbler", of course) that makes primarily handsewn shoes, and makes most of its shoes in Maine (the exception, the trench boot, is made in New York). Oak Street Bootmakers make most of their shoes with Horween Chromexcel leather, the original pull-up aniline leather, which is still made in the Horween factory in Chicago. Chromexcel is used by most manufacturers of high-quality handsewn shoes, with good reason.
Their shoes are not made-to-order, so they will ship to you pretty quickly.
Subjective: Style and Quality
Oak Street Bootmakers have an edge over their competitors in website design, and are the undisputed masters of taking flattering photos of their own products. That said, their products do measure up very well to the competition. The construction is good, and the comfort is excellent. While the array of colors and leathers is pretty limited, the options available are all very tasteful, if a little conservative. These make for very good basic handsewn shoes and boots.
Even their competitor Kyle Rancourt, who managed to say nothing nice about Quoddy, had to admit that Oak Street Bootmakers know what they're doing.
Their shoes run true to size, their boots run a half size large. Their website offers sizing tips for each shoe. This editor can say from experience that the camp boot runs a bit large but is still totally wearable if you order your regular size.
Oak Street Bootmakers are slightly more expensive than their competitors Quoddy and Rancourt & Co. While Rancourt offers their "Clymer" moc for $265, Oak Street Bootmakers offer their nearly-identical "Trail Oxford" for $296. In fairness, Rancourt's Clymer moc debuted after Oak Street Bootmakers were peaking in popularity. I'll leave that thought with you.
Shoes made for other retailers
While Oak Street Bootmakers don't seem to be going overboard with the exclusive shoes for retailers, they have made a few to this editor's knowledge. The first is the black version of the Trench boot made exclusively for Context. The second is a black bison leather chukka with a ripple sole for Need Supply. The third is a peanut suede trail oxford with a brick camp sole for Independence Chicago. The Toronto stockist Lost & Found offer a few unique models.
While you could get called a dad by wearing these with a #menswear fit, generally good things are said about Oak Street Bootmakers when mentioned. The brand is not terribly popular, but it is not unknown or unpopular, either.