James is one of the classic Anglo-Saxon names, a stalwart through the ages that is more popular—and yes, stylish—than ever today. It recently came out Number 1 in a poll of America's favorite boys' baby names, and is the most common male name, counting people of all ages, in the US.

A solid classic with plenty of history, Thomas strikes the balance between strength and gentleness. A favorite in the UK, a staple in France, and Australia, and never absent from the US Top 100, Thomas feels like a safe bet and a name that fits into any era.

Eugene is a classic that has rather lost its way. On the one hand, it's a grandpa, even great-grandpa name that hasn't been one of the cool kids recently—or to quote Jim Carrey, who bears this name in the middle spot, "You can never get too cool with a name like Eugene." The hero of Disney's Tangled felt the same way, when he changed his birth name of Eugene to the more romantic Flynn.

The name of an important ancient Roman emperor, Tiberius might sound a bit heavy for a modern boy to carry, but with the rise of Atticus, Tiberius and brothers begin to feel more baby-friendly, much in the same way as Old Testament names like Elijah and Isaiah have been rejuvenated.

Far more friendly and open than similar one-syllable names like Kent, Kurt, and Karl, it's been associated for more than half a century with actor Kirk Douglas, whose birth name was Issur Danielovitch Demsky.