Antonio - $210 Made in Italy

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You can wear this chukka boot for a decade straight. They’re Blake-stitched, which means you can have them resoled after a few years, and you’ll definitely want to. The pigment is hand applied, creating rich highs and lows in the Italian leather which only get better with time. These shoes pair really well with slim trousers and cuffed jeans, but the toe is designed to be a little bit fuller, so you can also wear them fuller cut pants, without your feet looking small. A good chukka is a timeless investment, and this is a pair your grandkids will want.

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