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Truman Says Fashion Advice: Our Two Cents on Penny Loafers

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Each week, the fashion editors at answer your fashion questions! Visit for new advice or seek answers to your own style quandaries by sending an email to!

Q:I was wondering if penny loafers are still ok to wear? I like to wear my Bass Weejuns all the time with jeans or khakis. They are really comfortable once they get broken in. I like the look, and I want to get a new pair but I want to know if they are in style?

A:The penny loafer is the ultimate in classic preppy footwear that has adorned men's feet since the mid-1930s when Bass debuted the Weejun. If prep-school style is in fashion -- and it always seems to be -- then you can work those classic kicks. The moccasin-inspired penny loafer is a footwear staple and you'll only start to see more of them as the fall season (and fall semester) approaches. Cole Haan, the esteemed footwear brand who has been hawking penny loafers for decades, is celebrating 80 years and highlighting a number of beautiful loafers in their spring and summer collections. So, if you can't find your beloved Bass Weejuns, Cole Haan will certainly satisfy your loafer craving. But please, avoid slipping a copper penny in the strap at all costs. Some people take fashion too literally.

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