Oak Street Bootmakers
![oak street bootmakers](https://footwearnews.com/wp-content/uploads/2017/04/oak-street-bootmakers.jpg?w=300)
Brown Beefroll Crepe Sole Penny Loafer, $344; oakstreetbootmakers.com
Brown Beefroll Crepe Sole Penny Loafer, $344; oakstreetbootmakers.com
John Addison Harness boot, $488; thefryecompany.com
1978 New Balance, $149.99; newbalance.com
Original 1000 Mile Boot, $360; wolverine.com
Piedmont Slip-On, $130; keenfootwear.com
Strand Cap-toe Oxfords, $395; allenedmonds.com
Men’s Chamberlain USA Cap Toe Boot, $450; eastlandshoe.com