Wolf & Shepherd's beautiful Breakaway Boots are made of full-grain Italian calfskin and are so light I wore them jogging. Seriously.
I'd been hearing about this brand for a few years before getting a pair. The company's claim to fame is its hybridization of dress and running shoes. Wolf & Shepherd was founded in 2014 by Justin Schneider, a former track and field star at Notre Dame who later designed running shoes for Adidas.
The boots are made in Portugal of full-grain Italian calfskin and come in black, chili (a reddish-brown), and honey (these last two colors have burnished toes). With its high shine and cap toe, these boots pair extremely well with a suit, but I've also styled them with black jeans, a T-shirt, and a Western snap shirt and they looked great.
The boots have a good bit of padding, including on the tongue and heel, while still maintaining a sleek profile. They incorporate memory foam and high-density ethylene-vinyl acetate (EVA), more commonly found in running shoes than in dress boots, as well as a carbon-fiber shank for stability. The boots have a lot of stretch and are lined in buttery soft sheepskin. They quickly conformed to my foot and there wasn't a break-in period to speak of.
For this story I threw them on and went for a run to see if the hype lived up to the reality. Although the experience was slightly embarrassing — apparently no one's seen a guy jogging in dress boots before — it was not physically uncomfortable. Only my pride hurt from the weird looks of the passerby. The mile-long jog was downright enjoyable. I wouldn't make a habit of it, though, since they're $395 dress boots.
Unlike most of the footwear in this guide, the Breakaway is also more like a running shoe in that the sole is glued on rather than attached via a Goodyear welt. Boot mavens tend to have a problem with a glued sole because it's harder to resole them, among other reasons. That being said, the boot has been specifically designed so that it can be resoled by the company (for $80, a decent price, actually), but not by a cobbler. I've read that these boots run small but the fit was spot on for me. If you have a wide foot you may be out of luck; they don't currently offer the boot in wide sizes.
Pros: Super lightweight and comfortable, nicely padded while maintaining a sleek profile, looks great with a suit
Cons: A bit on the pricier side, can't be resoled by a cobbler, limited sizing for guys with wide feet