A big trend we are noticing for fall is the return of the penny loafer. For many, this classic shoe has never truly gone out of style, but simply updated. First introduced in 1936 by G.H. Bass & Co who put a stylish spin on a Norwegian farm shoe designed for "loafing in the field", the Weejun became immensely popular by Prep School students during the 1950s. There are two theories as to the origin of the term "penny loafer", one stating it was started by students merly wishing to make a fashion statement when they notices the notch at the top was the perfect size for fitting a penny, while the other theory states that two pennies were enough to make an emergency call in the 1930s. Regardless of how it got its name, the penny loafer has been a classic footwear staple ever since.

While the classic burgundy color was always been a favorite of mine, for some the look can be a bit too dressy (even though the penny loafer is in essence a "casual" shoe). For that reason we're looking at 5 of the best new and classic versions of the penny loafer in various materials and colors.



G.H. Bass Classic Beefroll Weejuns - The Classic which never goes out of style. Stiff and definitely requiring some breaking in, these shoes will mold to the shape of your feet and will only look better with age. $128


J.Crew Kenton Suede Loafer- A great alternative to leather and perfect for fall, these loafers are finished with a Goodyear welt which can be resoled when they wear down. $198


Allen Edmonds Kenwood Penny Loafers - Boasting plenty of subtle style updates to the classic penny loafers, Allen Edmonds hand-sewn loafers are a favorite among those looking for a classic, made in America shoe. This tan color way is fantastic, more casual look which is perfect for wearing pretty much anywhere. $250


Cole Hann Pinch Grand Penny Loafer - My father in law swears by these Cole Hann penny loafers. Utilizing Cole Hanns Grand. OS technology which allows for greater flexibility, reduced weight and increased cushioning making the shoes feel like they're already broken in. $168


Palace Vigblu Penny Loafer- Lastly, a bit of a wild card but definitely a favorite from a London skate company of all places! These bright blue loafers from UK-based Palace Skateboards continues the brand's enigma of "high fashion or skate brand". Handmade in Portugal and toted as being "super gangster", the shoes come with two gold-plated Palace Pennies which gives the loafers a totally different look. While they don't encourage skating in the shoes, these are loafers have been turning heads all over the internet and secures the Penny Loafer's return. $276