I’m not sure where the Monkey boot got its name, *quick Google* and no decent explanation. They were the standard issue Czechoslovakian army boot of WW2. That's all I can find out.
I’ve been wearing mine all winter and they seem to go with everything. They dress down a smart trouser without looking forced and keep a jean looking smart without looking sloppy.
Their history as a skinhead’s boot of choice doesn’t hurt, plus they’re really comfortable. When I was at the Pitti menswear show in Florence, last summer, they looked fresh and contemporary and there were a lot of brands producing them for this spring season.
There’s something solid and traditional yet also street about the monkey boot. They’re the kind of boot you don't notice at first, but the more you look, the bigger the appreciation. These polished toe cap version from Grenson have a nice contrast between the front and the grained leather and the solid, wedged sole adds a modern touch.
Left & Below - Grenson - Andy - £225