Sean Sullivan of The Impossible Cool on Jack Dempsey, One Tough Style Icon

In these six photos, Dempsey shows that classic men's style can be as simple as well-shined shoes, a proper Borsalino, and a respect for the double-breasted dinner jacket.

Jack Dempsey, World Heavyweight Champion from 1919 to 1926 with 61 wins (50 by KO)—he existed in a time when men still stood up as a lady entered the room and showboating was better left in the casino. In these six photos, Dempsey shows that classic men's style can be as simple as well-shined shoes, a proper Borsalino, and a respect for the double-breasted dinner jacket.

Happiness is a well-stocked travel bag.

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A brawny cardigan

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It's fine if someone shows up to the party with the same thing on as you,

just as long as you wear it better--or if the other person is Babe Ruth.

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Long legs capped off with perfectly polished shoes

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Freemans Sporting Club circa 1924

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You can't ever lose with a good cut and a heavy tweed.

To explore Sean's fantastic collection of inspiring pics, head over to his blog, The Impossible Cool.

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