Exactly one year ago today, Men’s Journal endorsed the timeless burgundy penny loafer as the ideal transitional shoe for that weird, in between time when fall has started, but you’re still waiting for it to get too cold out. And because some things will always be in style, we’d like to reaffirm our commitment to this most classic of dress shoe staples.
That’s because everyone from old-school style icons like JFK to new-age cool guys like Ryan Gosling have been known to wear them — and so have countless regular joes like us. They’re so ubiquitous that you can find them at every price point, from the relatively inexpensive $110 original Bass Weejuns (the models the Kennedy brothers were known to sport) to the handmade Edward Green loafers you see above, which will run you a blistering (but kinda worth it) $1,220.
The reason for their long-lasting appeal? They just go with everything. They’re an ideal complement for most suits, and work just as well with jeans when you want to class up a more casual look. As for whether you need to put a penny in the genre-defining slot on the vamp of this style, we’ll echo the immortal words of our editorial director Mike Conklin: “You’ll have to take a good long look at yourself and make that decision on your own.”