Of a Kind

Sure, it’s very early in the season, but not too early to assert that Penny Stock’s if fall’s best oxford. —erica

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Of a Kind

Something about these Penny Stock board shorts is so retro cool—straight off a Gidget suitor, really. —erica

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Of a Kind

If your favorite jeans mated with your best chinos, you’d get these cobalt blue Penny Stock pants. And you’d be a damn happy guy. —erica

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Of a Kind

These Penny Stock pants aren’t army green or moss green. They’re perfect green. —erica

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In Character: Jake Ryan

The beauty of the Sixteen Candles heartthrob—dare we say the eighties-movie heartthrob—is that while we were very aware of his coolness, he never exactly looked the part. Please wear your broadest smile (and broadest shoulders) along with his creased, good-boy uniform.

A go-to plaid button-down, pressed. The most popular boy in school would not have been intimidated by the Easter egg madness of this Gitman Brothers x Opening Ceremony one.

A pair of Penny Stock khakis—the least dorky cut around. (Avail at Blackbird.)

Something fitted and Fair Isle, a look that Rag & Bone has mastered for fall. (Avail at Bergdorf Goodman.)

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