It’s probably not news to you that boat shoes have been enjoying a moment. Worried lacing up a pair will mark you as a sailor—or, worse yet, a finance guy en route to a Nantucket bachelor party? Don’t be: these Timberland boat shoes have weathered significantly worse than mere stolen valor accusations, and they happen to be the perfect gateway (or, uh, marina) to the genre.

If that name doesn’t ring any bells, it might be because it’s new: for years, Timberland simply called silhouette the Three-Eye Lug Sole Shoe, until the brand wisely leaned into the rising nautical-style tide. Smart move. With its handsewn moc-toe upper and 360-eyelet lacing system, it looks every bit the classic boat shoe. Except, that is, for its beefy lug sole, a savvy addition that takes the silhouette from preppy to damn-near-punk in the time it takes for you to clock it. You can still rock a pair with chinos and a polo, but that telltale sole means they’ll take just as well to baggy jeans and a hoodie, or cargo pants and a windbreaker.