good trail boot is hard to find. So, for that matter, is a comfortable brogue. A shoe that marries the thoughtful design of the former with the rugged construction of the latter? Prior to trying on the Long Branch Lug-Sole Brogue from revered shoe fabricator Allen Edmonds, we would have laughed at the very idea. But these stunningly comfortable pebble-grain leather boots are carefully detailed with wing-tip perforations and outfitted with a thick Vibram sole, making them dressy enough to wear all day at the office and substantial enough to keep on for your post-work walk with the dog.

The Long Branches are a bit heavy, granted, but heavy isn't a bad thing when the weight is the result of thick leather and welt construction. This is especially true given that these boots break in quickly – extremely quickly. The Long Branches are annoyingly stiff for all of 10 minutes before they start conforming to wearers' ankles and feet. Thanks to aluminum hooks on the shins, these made-in-Wisconsin boots can also be strapped on extremely tight, which helps on both the first day you own them and every day it rains. And yes, you can wear these boots in the rain or even the snow. The soles are thick enough and the leather is tough enough that, with a bit of waterproofing, the Long Branches can take on just about anything the elements have to offer.

After that storm, or hike, or backyard tussle, you just need to buff these guys and they're ready to go back to work. With jeans or dark slacks, they send a simple message: I've got places to be. Whether those places are boardrooms or mountaintops is yours to determine. [$350; orvis.com]