Probably is one of the most masculine shoes in men's wear and it's called "Chukka boots". It was made for troops during World War II for desert combat, back then they called "desert boot".
Chukka been worn by many generation of men. Most successful brand and most recognized for this style of men's boot would be "Clarks" Today even Nike and Vans got some Chukkas for you gentlemen. They don't come only in brown suede no more, they do come in colors, prints and personalities to match yours. Due to it's versatility, it goes with many outfits, can be worn in many seasons. It is also most traveler's best friend, with Chukka they rarely need to pack more shoes for their trips.