Style file: Benjamin Kheng’s five favourite hats

Benjamin Kheng has “a morbid obsession with hats”, he says.

“I got a couple of Herschel hats from fans, just because they know I’m a big hat guy. It’s quite nice of them. They got my head shape wrong, though — everyone thinks I have a smaller head than I actually have. My ego is terrible,” he quipped.

“I promise (that other than the hat obsession), I am a well-adjusted human being,” he said.

He did not hesitate to give TODAY a show-and-tell session featuring his five favourite hats — a shortlist that was curated with much struggle and gnashing of teeth, considering these babies only make up about one-fifth of his headgear collection.

STAR WARS CAP. “This cap is super cool. I am a massive Star Wars nerd and I think one of the coolest points in my life was being invited to the premiere of Episode VII in Los Angeles a couple of years ago. I freaked out massively. I couldn’t contain myself and decided that I obviously had to get some memorabilia. So I went to a hat store and bought a hat. This is the sign of the rebellion, ala Luke Skywalker, ala Leia.”

NEWSBOY HAT. “This newsboy hat is my oldest hat. I have had it since I was 17. I bought it in Poly because when you get into Poly, you want to reinvent yourself ... This was about exploring my fashion choices, in which I have made many errors. This was not one of them — I love this hat.”

BROWN WIDE-BRIMMED HAT. “This is my most sentimental hat. I even named it Dylan — for the famous Dylan, Bob. This was given to me by a friend just as The Sam Willows started, and I have worn it for a lot of gigs so there are a lot of photos of me in it. And it probably should not go near anyone else because it is very old.”

BLACK CAP. “I am a big sports fan. This is unfortunately not my favourite basketball team, but it is the most aesthetic, because Jay-Z is the owner of the Brooklyn Nets and they are a cool team. I bought this in Toronto when I was watching a game: The Nets and the Raptors. That was a great game. But I love this because it is just really classic.”

TAUPE HAT. “This one is a bit out of shape, but it is a beautiful colour. I guess it is a classic fedora-style hat. It is slightly too big for my head, so I only wear it when I have grown-out hair.”