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Loafers might remind you somewhat of an older gentlemen, but they’re the ones who’ve got it sorted (especially the italian type) – they’re not going to bore anyone with Paleo diet or gym regime, probably own a car, perhaps a yacht, and can cultivate an air of sophistication due to having done, well, more.
This definitely is something to aspire to, and Loafers can be part of that look – slip ons for the smart set. Tassels lend to the classic look, but if that’s a step too far then Penny Loafers are a great stater shoe, and are equally great with jean or a suit.