Image: Oak Street Bootmakers

When it comes to footwear, there are probably a few staple items that every guy should have, but a loafer is certainly the most versatile of the bunch.  There are plenty of versions out there, but for us a classic Beefroll Penny is the way to go.   This is one of those shoes that you should invest in a quality pair from the get go as they will never be out of style.  Some of our favorites come from Oak Street Bootmakers.

Crafted in Maine by some of the best in the business, the Oak Street Beefroll Loafers have remained in heavy rotation since the day we got them.  Made from Horween Chromexcel leather uppers mated to a leather sole and stacked leather heel, these loafers are fully re-craftable, and will literally last a lifetime.  While the navy pair is certain to turn some heads, stick with the brown or natural options for your first pair.  Trust us, once you have them, you’ll end up wearing these loafers with just about everything.