Clunky yet cuddly, Wilbur is a stylish name in the UK where it currently sits in the Top 600, as cool as Rupert or Wilfred. Its merits are starting to be rediscovered in the US, where it was last truly popular more than a century ago. A recent year saw it given to 42 boys.

Henry is well and truly back in style. The classic returned to the Top 10 in the US in 2021 for the first time in over a century, and as of 2024, sits at Number 6. Like James and Theodore, Henry is a strong, traditional name that also manages to feel stylish and gentle.

Everett is a preppy but outdoorsy name, with wintery New England vibes. In the last decade, it’s had a leap in popularity, perhaps because of its similarity to trendy girls’ names like Ava and Scarlett, or perhaps because it offers a fresh alternative to 90’s style Evan and Brett.

Classic and elegant but with boyish charm, Theodore has become hit name in recent years, vaulting into the US Top 10 in 2021 for the first time ever and into the Top 5 in 2024. A favorite in English speaking countries, it also ranks highly across the UK and Ireland, and in Canada, New Zealand, and Australia.

Arthur, once the shining head of the Knights of the Round Table, is, after decades of neglect, now being polished up and restored by stylish parents, inspired perhaps by the new generation of royals. Arthur has led the list of possible names for the young British princes, chosen as a middle name for Prince Louis, son of William and Catherine, Prince and Princess of Wales.

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.

Oscar is one of the most stylish Old Man Names of our era. While it's softened slightly in popularity over the past 20 years, that may be considered a very good thing.

William is one of the most enduring of classic names for boys. It's also among the most popular boys' names, as American parents see it as being ideally conservative yet contemporary, and hands-down the most popular baby name beginning with W of all time.

Jack may have fallen from its Number 1 place in England, but in the US it's as popular as it was at its height in the 1920s and 1930s. A durable, cheery, everyman form of John, Jack ranks as one of the most popular boy names starting with J.

Vincent is a name with a complex image. After being quietly used for centuries, it is suddenly seeming stylish, along wih other V names. Even the nickname Vince has been given a reprieve via actor Vince Vaughn and country singer Vince Gill. Vin Diesel was born with the more prosaic name Mark Vincent.

Leo is a strong-yet-friendly name that was common among the Romans, used for fourteen popes, and is now at its highest point ever in the US thanks in part to Leonardo "Leo" DiCaprio.

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.

This no-nonsense German variation of Charles is strong and sturdy. A top choice throughout the 20th century, Carl is now verging on falling off the charts.

Benjamin is a biblical name that has enjoyed widespread favor for decades, ranking in the US Top 50 for almost half a century and the Top 10 from 2015 until 2023.

John reigned as the most popular of all boys' Christian names for 400 years, from the time the first Crusaders carried it back to Britain until the 1950s. Then American baby namers finally seemed to tire of this straight-arrow, almost anonymous John Doe of names, replacing it with fancier forms like Jonathan and the imported Sean and Ian.

Kate and William shocked the world when they announced that they'd named their third child Louis, or Prince Louis Arthur Charles, to be more precise. But we've been predicting a comeback for this classic name for a long time.

David is an enduring worldwide classic, used from ancient times to the present day.

Walter was seen as a noble name in the Sir Walter Raleigh and Sir Walter Scott era, but it then spent decades in baby name limbo. Now quite a few independent-minded parents are looking at it as a renewable, slightly quirky, classic, stronger and more distinctive than James or John, second only to William among the handsome classic boy baby names starting with W.

Daniel is one of only a handful of male names that sounds both classic and modern, strong yet approachable, and popular but not cliched. It also has a solid Old Testament pedigree. The only real downside: There are about 10,000 Daniels named each year, making it a less than distinctive choice.

Charlie derives, of course, from the classic name Charles which, in turn, comes from a German word meaning "free man." Charles became very popular in France during the Middle Ages due to the fame of Charles the Great, also known as Charlemagne. Charley is an alternate spelling.