The Penny Loafer: The Ivy League’s Style Staple

In between “the wars,” men on campuses in the east were starting to sport a look that was a bit more understated, more comfortable and less formal. The jackets got tweedier, the sweaters and shirts were crafted from more casual fabrics, and the look was more “dressed down,” than “dressed up.”

In the 1930’s, Barrie Ltd. was located at 260 York Street in New Haven, just a handful of blocks away from Yale’s campus.  They introduced a “penny” style loafer, described in advertisements of the day as a “Norwegian Moccasin,” a shoe which offered “more sturdiness, while retaining the comfort of a moccasin.” You may have heard of “Weejun” loafers by the Bass Company? That’s simply a phonetic contraction of “Norwegian.”

Clean, plain and comfortable like the oxford shirts and flat-front trousers they bought from J. Press and Brooks Brothers, the preppy penny was free of laces, tassels or any fussy brogueing. Basically this was a nicely-crafted, comfortable leather shoe that eschewed all of the trappings of business footwear. Students lined up to buy them. That was more than 80 years ago, and the penny loafer is still popular.

Model is wearing Samuel Hubbard Ivy Legend penny loafers in Whiskey.

While mostly a casual shoe, the stylish penny has been worn artfully with everything from shorts to suits, with khakis and jeans in between. I’ve seen them rocked solidly with white socks, argyles and the ultra-preppy-no-socks look.

Samuel Hubbard’s “penny” offering, The Ivy Legend slip-on shoe, pays tribute to the storied legacy of this iconic American product, which is as much a part of our cultural fabric as blue jeans and Coca-Cola. The silky smooth interior is leather lined. The hand-rubbed finish is luxurious, and the out-of-the-box comfort is…well…trademark Hubbard!

Samuel Hubbard Ivy Legend penny loafers in Cordovan, Black and Whiskey Leathers

Click here to shop the Ivy Legend now. 


Brian P. Cleary is an American humorist, poet, United States patent holder, inventor and author. The bow-tie wearing children’s author is best known for his books that explore grammar in humorous ways written for grade-school children. To learn more about Brian and to see his work, click here