If you're all in on old school these Reebok classic leather shoes go all the way. The distressed leather upper adds sophisticated detail, while the gum rubber on the outsole completes the coveted look. The tried-and-true silhouette looks timeless on the street or during the work day.

Reebok was founded for one of the best reasons possible: athletes wanted to run faster. So in the 1890s, Joseph William Foster made some of the first known running shoes with spikes in them. By 1895, he was in business making shoes by hand for top runners; and before long his fledgling company, J.W. Foster and Sons, developed an international clientele of distinguished athletes.