I've been eyeing these for a while, and once they went on sale they immediately went straight to my cart for purchase. The square moc toe with the side eyelets and crepe sole is the ultimate shoe trifecta, if you ask me. I've also been wearing a lot of colors in the taupe family lately, and these look great with some cargos, especially cinched at the ankle.

Kleman makes some of the best utilitarian shoes on the market and these Chelsea boots are no different. The rich burgundy color is perfect for winter, but subtle enough to wear with pretty much anything. And the heavy-duty rubber outsole means they'll take you through the worst of winter and the wettest of spring weather.

Boots that wear like sneakers can always be a stretch but Yuketen founder, Yuki Matsuda, took two decades worth of research to figure out how to do it. These boots are made from the label's signature “flesh-out” leather and are set on top of a thick Vibram sole for maximum support. Pair this tobacco colorway with some green fatigues and a nice denim overshirt to give you the classic Americana vibe.

Whether you're running on the treadmill or down a trail, these Free Runs from Nike can adapt to any workout environment. The brown suede gives off an outdoorsy vibe and the perforation allows for breathability as you're burning those calories off. And bonus: They're on sale, so it'll make it that much easier to put these into your gym attire rotation.