The fashion world pondered the future of the iconic shoe after learning that a presidential order might eliminate the penny.

Go ahead and see for yourself how well they pair with anything from jeans to suit pants. Why we love this brand: It’s one thing to be the company that invented penny loafers—it’s another to ...

You might like your classic black penny loafers with bright white calf socks ... or add a distinguished flair to a pair of jeans. We recommend Everlane's Modern Loafer first because the leather ...

Rather than over-the-top Hollywood glam, Diaz opted for black high-rise jeans paired with a sheer top and penny loafers. A tailored wool coat, trailing on the purple carpet softly behind Diaz ...