You don't have to work on a ranch to wear roper boots, although it wouldn't hurt. Over the last few months, we've started seeing them hit the mainstream fashion world, and we think they're here to stay. Chelsea boots had a chokehold on men's fashion close to a decade ago, but it's the ropers' turn now. This pair from Tecovas are designed in Texas and then handcrafted in Léon, Mexico. It's the brand's first wedge sole roper built for rugged performance with a focus on comfort. The one-inch Vibram 4014 Cristy outsole provides stability and excellent traction for any terrain. With treated leather and weather-resistant seams, these should be easy to keep clean. Wearing denim-on-denim may be a little too on the nose, so freak these with a heavyweight hoodie and some lived-in fatigues for an updated approach.

Keen is known for their signature UNEEK sandals, but for winter they've created a chukka to help beat inclement weather. Although it's a durable leather boot, it has the same comfort as your favorite sneakers thanks to the extra-grippy ubber outsole—which also makes this an easy weather-appropriate option to reach for during those wet, snowy days. Plus, the shoes come with three sets of laces to customize your look and the lace-lock system is made of recycled PET plastic and bungee cord, so you can feel great about wearing these.

A few years ago Frank Ocean wore hiking boots, vintage straight-fit denim, and a hooded down jacket—he was ahead much like his music, and you might say he set the landscape for how most guys dress today. What's not to love about hiking boots? This pair from Greats comes in a beautiful tan color that's versatile to match with anything. Hard-wearing and refined, they're made in Portugal from premium textured leather, with a gusseted tongue construction to keep out moisture, and speed hooks for easy lacing. Wear what you want with these; however, looking to Frank for inspiration isn't a bad place to start.