I'll be honest, I've always had a thing for moc-toe footwear. Whether it was a pair of classic Red Wings or some OG suede Wallabees, they always had such a distinct look—substantial and utilitarian yet still somehow elegant. It's the kind of juxtaposition you see in old cars from the 1970s. Models like the Chevy Blazer K5 or BMW 2002 look decidedly cooler these days.

And it's the same thing with the classic moc-toe after years of taking a backseat to slimmer, more streamlined footwear. But now, you might say that bigger is better. And the best moc-toe boots, chukkas and lace-up shoes right now have a rakish ruggedness. Each of the options here are crafted from strong leathers or suede and have a sturdy sole, with some featuring a more comfortable natural crepe rubber while others are grounded with hardwearing Vibram and heavy duty lug outsoles.

What's more, they have the ability to change vibes with what you're pairing them with. Pull them on with a suit or wide-leg trousers and they look elevated and angular. Throw them on with jeans and a corduroy jacket and they now look classic and ready to stomp some leaves. So find a pair that works for your personal style and budget and start wearing the hell out of them.