To say that Bill Hader is uncomfortable with the idea of being an “unlikely sex symbol” would be an understatement. His whole body instantly recoils at the notion, as if rejecting a demon. It’s partly the Midwestern humbleness of the Oklahoma-born-and-raised performer that keeps him from accepting that people might find him attractive. It’s also that he sometimes gets confused with author Stephen King, who is nearly twice his age, or unflatteringly compared with a not-so-handsome actor from a popular network sitcom. Comedians and actors are not generally known for their introversion or modesty, but Hader is not most comedic actors. A hyper-talented impressionist who can also fully inhabit characters, he says his comedy has always come from his anxiety.

He developed his comedic side as a means of becoming comfortable with other people. “When I am ‘on’ a lot, I’ve learned, it’s because I’m nervous and I’m wanting the room to be filled with friends, so if people start laughing, I’m like, ‘OK, I’m in a room with friends,’ ” he says. “And then I can kind of relax and be vulnerable or mess up. To me, it’s the same as walking up and introducing yourself: ‘Hi, where are you from?’ Instead I tell a joke and try to make people laugh.”

His ability to do just that led to a notable nine-year stretch on Saturday Night Live that brought him fame and fortune, but his nerves never subsided. “Like, it never went away,” he says, smiling. Surely he must have had some enjoyment then for the anticipation and excitement of it all? “No, no, no. I hate it.”

Image zoom Bill Hader in a Louis Vuitton Men’s jacket and T-shirt, Brunello Cucinelli pants from Saks Fifth Avenue, and Koio sneakers. Photographed by Beau Grealy.

Hader’s recent pivot as the star, co-creator, and executive producer of the HBO show Barry, in which he plays a former Marine–turned–assassin–turned–actor, earned him a best actor Emmy in September. And with the show’s success came a sartorial leap that Hader had never attempted before. This happened by way of an intervention. “While we were in postproduction for this season of Barry, I was saying, ‘Should I get a haircut?’ And my assistant Nicky Hirschhorn said, ‘No. You know what you should do? You should wear different clothes.’ ”

Hirschhorn showed him a social-media account called Bill Hader Needs Clothes, in which Hader is seen recycling the same few items. “There’s, like, full Tumblr accounts about how bad my fashion is, that I only wear flannel shirts, jeans, and New Balances, which is pretty accurate.” He laughs, but he took the criticism to heart. “When I was growing up in Oklahoma, clothes were never a thing I thought of. I don’t know designers. I mean, I got a Dior suit for the Emmys, and I remember a friend of mine was like, ‘Oh, who are you wearing to the Emmys?’ And I was like, ‘It’s D-I-O-R.’ I couldn’t pronounce it.”

Hader took on the challenge, and Hirschhorn hired stylist Mark Holmes (who also worked on this story). “He basically came over and taught me how to dress,” Hader says. Having opened himself up to the possibilities of wearing nice clothes, he has found things he actually likes. “I like white Stan Smith Adidas,” he says, pointing to the ones he’s wearing today. “I kind of went overboard with Worn Free T-shirts. I was buying a lot of those. And so to offset it, Mark was like, ‘Let’s do non-logo shirts, just solid white and black and stuff.’ So I’ve been enjoying wearing those. Rag & Bone I like. And Theory shirts fit me well because I have really long arms.”

Image zoom Bill Hader in a Dior Men jacket, sweater, and pants. Photographed by Beau Grealy.

Learning to enjoy wearing clothes has been a useful exercise for Hader, who practices Transcendental Meditation to get out of his head. “I kind of have a weird reaction to feeling like I’m being vain, because I’m from the Midwest. But then it’s, like, I’m a father, and I have my own show. I need to be more of an adult and just a little bit more presentable,” he says, chuckling. “And when I started wearing things, I initially felt incredibly uncomfortable, and then I actually enjoyed it.”

He also wanted to dress age-appropriately and find his own boundaries for style. “You don’t want to be the guy in his 40s dressing like a 20-year-old slob.” Hader says once he got past his self-consciousness, he felt like, “ ‘Oh, this gives me more confidence. I see why people get into clothes.’ ”

Hader admits that feeling self-confident is still a daily struggle. “The whole confidence thing is a weird one. It depends on what day it is.” He recently opened up about this topic in a YouTube video that has amassed nearly a million views. His intention was to help others who might be feeling similarly. “I never thought of it as any sort of stigma. It was just a thing I had to work through. When I realized how bad my anxiety was, I went online to look for help, but none of it was hitting the way I was feeling. So it was kind of like, ‘Well, if someone’s feeling the way I am, maybe [the video] will help them, especially young people.’ ”

Hader has also taken on exercise to get ripped for his leading-man role on Barry. “I work with a trainer. It’s nice to do that thing where you start and you can’t do something and then after a month you can do, like, pull-ups. Suddenly you go, ‘Oh my god. I just did 10 pull-ups. I can’t believe I just did that.’ It’s a consistency thing. The same thing with meditation. That helps me a lot.”

Image zoom Bill Hader in a Brunello Cucinelli suit, a Calvin Klein Underwear T-shirt, and Koio sneakers. Photographed by Beau Grealy.

Having a self-imposed structure does too. “Keeping to some sort of program helps when I’m writing,” he says. “I think it’s just about keeping disciplined. But part of that discipline is watching a movie, reading, meditating, listening to music, and getting inspired, just living life.” He cites Brian Eno, the Clean, and Frank Zappa as musicians he loves as well as newer artists like Angel Olsen. On TV he enjoys Fleabag, What We Do in the Shadows, and the occasional trashy true-crime documentary.

He took a role in It Chapter Two because he thought it would be fun to do a horror movie. His own taste in horror tends more toward suspense thrillers than slashers, but he is an avid consumer of movies of all brows. He mentions directors like Akira Kurosawa, Hal Ashby, and Yasujirō Ozu in a long list of his favorites, but he also unwinds with John Wick movies.

When Hader talks about spending time with his three young daughters (with his ex-wife, filmmaker Maggie Carey), he lights up. “They’re getting to a place where they have their own likes and dislikes, and it’s fun to just see that,” he says. They’re not allowed to watch Barry, but they’ve seen their dad on SNL, he says, making a self-deprecating joke about how they preferred other cast members and asked to see the digital shorts instead.

Back to that unlikely-sex-symbol thing. In part because he considers himself the dad who is “burning pancakes for his kids in the morning,” Hader says he was totally confused when a friend told him that people were “thirsting for him” on the Internet and forwarded him a salacious article from The Cut about how hot he was.

“I didn’t know what that meant,” says Hader. “They’re what? At the what? I don’t understand it at all.” He thinks for a minute, then laughs. “I think it’s good to have humility, but I might have...too much of it.”

Photographed by Beau Grealy. Styling: Mark Holmes. Groomer: Catherine Furniss.