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.

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.

Wyatt has been hot, which is to say cool, for several years now. With its easy Wyatt Earpish cowboy charm, it's relaxed but still highly respectable.

Reminiscent of the Old West, with rugged charm and a gentle, easy-going feel, Wesley has long been a staple on the US charts.

Long associated with the Churchill family and common in the West Indies, the distinguished Winston is back in style having been slightly neglected in the US after its brief flash of popularity during World War II. Familiar in England and Wales, recent years have seen in re-enter the Top 500 in the States.

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.

Wells is a newly-famous baby name thanks to pregnancy guru Rosie Pope, who uses it as the short form of the buttoned-up Wellington, name of her youngest child.

Walker is both a Waspy surname name—as in the W in George W. Bush—but it also has a gentle ambling quality and a creative connection to such greats as writer Walker Percy and photographer Walker Evans, whose father was also named Walker.

With its rugged, country charm and confident sounds, Waylon is among the wave of Old Western names that parents are choosing.

Weston has gone from being a Jane Austenish British surname to a first name with a relaxed American western cowboy feel. Along with other trendy 'n'-ending boys’ names, Weston is rising in popularity, and is now more popular than ever, ranking in the Top 100 since 2021.

When Marion Michael Morrison became John Wayne around 1930, his last name took on an air of cowboy cool that lasted about thirty years. These days however, Wayne has been replaced by Waylon, Wesley, and Wyatt, and it now resides in the grandpa name camp, alongside Stan, Bruce, and Ronald. For some, thus may well be its selling point. < br>
Originally an occupational surname, Wayne comes from the Old English wægn meaning "wagon". Associated with wagon makers, it rose to popularity as a give name in the mid-20th-century. Notable bearers include footballer Wayne Rooney, hockey player Wayne Gretzky (generally considered the greatest player in the history of the sport), and rapper Lil Wayne.

Rugged, outdoorsy, and full of energy, Wilder entered the US Top 1000 back in 2015. Part bad boy, part Western, part preppy, and part nature-loving, Wilder is given to nearly 800 babies each year.

Wilfred is one of those Old Man Names that still sounds fusty in the US but is fashionable in the UK. It comes with readymade short forms Will, Wilf, or Fred and might make an adventurous alternative to the ubiquitous William. The central character of Walter Scott's Ivanhoe is the knight Wilfred of Ivanhoe while Wilfred Owen is a well-known British poet, noteworthy for his war poetry.

Short and cool with rugged charm, Wes is a rising star in the US, climbing the charts along side Wesley and Weston and joining other one syllable options such as Mack, Jett, Tate, and Brooks. Filmmakers Wes Anderson and Wes Craven lend the name a stylish and creative air, but it also has Old Western undertones thanks to its literal meaning, "west".

Wade has never been outside the US Top 1000 for boys - there's a reason for that. It has a clean spelling, fresh sound and is neither too trendy (unlike Kade or Cade) or too old-school (like Richard or Albert). We think Wade is a winning name.

Wallace is so square could almost be ripe for a turnaround, especially with the hipness imparted by the British Claymation series Wallace & Gromit. And Wally makes an adorable Leave it to Beaver retro-style nickname.

Wynn or Wyn is a Welsh male name deriving from the very productive gwyn element, which forms part of all Welsh names ending -wyn or -wen, as well as the Gwen names and the Irish Fin- names. Wynn is a soft and gentle yet sturdy choice which feels quietly timeless and charming.

Wolf is a name with a split personality. It can be seen as one of the fierce animal names, like Fox and Bear and Puma, with a touch of the werewolf, or it can be viewed as a quieter, Wolf Blitzer kind of name, fairly common in German (where is pronounced Vulf) and Jewish families, sometimes as a short form of Wolfgang, or even Wolfram or Wolfhart.

Wiley may be considered a variation of Wylie, a Scottish diminutive of strong, classic William. As such, it may work an appealing way to honor a Bill, Will, or William, or as an alternative to popular Liam.

Alternatively, Wiley may be considered a surname-style name, ultimately derived from two English places: Willey (meaning "clearing of willows") or Wylye (the name of a river, meaning "tricky").

Aside from President Wilson (born Thomas), most Woodrows, including Herman, Guthrie, and Harrelson, have chosen to be known as Woody, which says it all.