Say hello to your new best friend: Penny.

The penny loafer is a classic style that has stood the test of time and transcended all of the fall shoe trends that have cycled through fashion week and street style coverage year after year. Pro tip: Invest in a well-made pair that will sustain years of wear, because these capsule wardrobe must-haves will never go out of style.

Have a peek at some of our favorite penny loafer street style moments and then keep scrolling for the styles we're loving right now.

woman in white neutral outfit
| image courtesy of net-a-porter |
woman walking on street
| image courtesy of net-a-porter |
woman in white outfit
| image courtesy of net-a-porter |
woman in white jumpsuit
| image courtesy of Who What Wear | photography by @thestylestalker |
woman walking on street
| image courtesy of Refinery29 | photography by Victoria Adamson |
woman in all black

| image courtesy of The Cut | photography by @jaiperdumaveste |

We've rounded up a few of our favorite styles. Take a peek and then add to cart.

Frame Le Ayana Loafer
J. Crew Winona Penny Loafer

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