What makes a name everlastingly cool? Mix an element of edge and swagger, a seductive sound, a charismatic cultural association, plus a certain timeless quality and you get what the following 12 cool boy names have—the ability to stay cool over time.

　　Ray – Ray, with its many shades of meaning, is forever jazzy and cool via its association with several iconic musicians—most particularly the legendary Ray Charles. Other names that share this jazzy vibe include Dexter, Bix, Clyde, Quincy and Louis.

　　Miles – Another major musical name, Miles conveys all the jazz charisma of Miles Davis. Miles has always been in the Top 1000, but is having a real moment, currently at a high of Number 107 (And 30 on Nameberry), helped as well by its stylish s-ending.

　　Sebastian –Sebastian mixes cool sophistication and swagger and a slightly exotic element that makes it appropriate for a romantic hero, a soccer star, or a real boy. This has allowed Sebastian to remain one of the most popular boy names and cool from the 1880s until now in countries from Sweden to Australia, Ireland to Norway to the US.

　　Sullivan – American baby namers have always found Irish names for boys to have a particular roguish charm, and yet big hits like Kevin and Brian and Ryan have lost their luster over the years. Though while Irish given names rise and fall, some of the surnames have the ability to feel cool over generations: classic film comedy film Sullivan’s Travels came out way back in 1941, but this good-natured name still retains its twinkly Celtic cool.

　　Chance – Tennessee Williams had the knack of creating character names with a certain intense cool. And so it was with Chance Wayne in Sweet Bird of Youth, portrayed by Paul Newman on film. Chance has that element of risk embedded in its meaning, and a vestiges of an old-time Mississippi gambler charm: eternally cool.

　　Wyatt – Since the Wild West days of Wyatt Earp, this name has retained its cowboy cool vibe. Names like Wyatt and Wylie and Cody have that special swagger that sticks to their image even as they more in and out of popularity.

　　Rafe – This British pronunciation of Ralph – as in actor Fiennes – takes it from stodgy to raffish in one fell swoop. Rafe can also be short for Raphael: either way, it makes a short, suave, and totally cool, name for a boy.

　　Axel – Despite its traditional Scandinavian roots, Axel gives off a heavy rock ‘n’ roll, Guns ‘n’ Roses vibe. That middle x adds a lot more pizzazz to its boisterous charm as well. So put this one in the category of party-boy cool.

　　Omar – With roots in the Old Testament and ties to the Persian poet Omar Khayyam and coolly sophisticated actors Omar Sharif and Omar Epps, Omar is one of the unique boy names that has smooth charm to spare. The open O sound makes it approachable and stylish, with a touch of the exotic.

　　Luca – Luke may be cool among Biblical names (and it is), but that extra Latinate a-ending takes Luca a step further into the charmed circle of cool. Many boy names ending in vowels like a and o often have a built-in element of, yes, cool.

　　Jude – Mix the sly grin of the young Jude Law with the plaintive lyric of the Beatles ode of comfort for John Lennon’s son Julian and you have a name that’s both strong and resonant, rich with meaning and charm—and forever cool.

　　Jack – The ultimate man of action name, Jack has been worn by a charismatic president (Kennedy), a bad-boy poet (Kerouac), a wily pirate (Sparrow), and even a pumpkin king (Skellington). And though it’s traditional, and it’s a large part roguish, too, a mix of Jack Nicholson and any of the many fictional Jacks.