TUDOR HERITAGE BLACK BAY HAMILTON KHAKI FIELD

$5,925, tudorwatch.com

The Tudor Black Bay might be the ideal piece to start a “proper” watch collection. It’s premium but not too expensive, it’s got history, and it’s a very attractive, wearable, everyday watch. $595, hamiltonwatch.com

This is a faithful recreation of its original 1960s forebearer and is true to Hamilton’s military heritage. The 38mm stainless steel case is paired with a durable NATO strap.