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G.H. Bass & Co.

Bass Men's Larson Weejuns Penny Loafer

Why we picked it

Keeneland in April is a dressed-up crowd; the original penny loafer walks paddock to clubhouse and back to the bourbon bar.

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Desert Boot, Beeswax Leather

Clarks Originals

Desert Boot, Beeswax Leather

Comfortable over miles of brick sidewalk and old districts, and dressy enough for a candlelight dinner after.

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