The Flag Day star sits down with the infamous Jackass to talk shop... and outfits.

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Style Crush Dylan Penn and Johnny Knoxville
The Admirer/ The Crush
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Dylan Penn knows how to work a red carpet. She did grow up watching her parents — actors Robin Wright and Sean Penn — get dressed up for one glamorous event after another, after all. Although she's no stranger to the Hollywood scene, this past summer the 30-year-old star of Flag Day took her own fashion game to new heights. Working with stylist Rachel Zoe, she stepped out in show-stopping looks from the likes of Chanel, Balmain, and Louis Vuitton at the Cannes Film Festival — earning her own rightful place at the top of the best-dressed lists. 

Since she's already established herself as a style star to watch, we asked Penn whom she looks to for fashion inspo. The slightly surprising (but entirely thrilling) answer: Johnny Knoxville. With his vintage tees, Dickies, and signature red Converse Chuck Taylors, it turns out that the Jackass Forever star, 50, has made quite an impression on Penn, who says that when she's not giving us a dreamy couture moment on the red carpet, her off-duty style mirrors Knoxville's own. 

For InStyle's October Style Crush feature, we connected the pair to chat all things fashion, from their approaches to comfort and red carpet risk-taking to a shared love of sweaters (hers, vintage Ralph Lauren; his, vintage…beer). Read their full chat, below.

Dylan Penn: Johnny, there's a lot I want to know about your style. 

Johnny Knoxville: I don't know what I know about style. I can't believe that I'm a style crush. I'm honored to be chosen.

Style Crush Dylan Penn and Johnny Knoxville
Chanel
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DP: Honestly, we dress very similarly day-to-day. You always looked good in Dickies, distressed old T-shirts, and Converse on Jackass, so I emulated. I don't like to use the word "tomboy," but that's my vibe when I'm not working. I already feel girlie, so I don't need to dress up.

JK: Ditto. I'm a total tomboy myself. [laughs] But I've never thought of myself as a fashion icon! I dress very simply. I have one pair of pants, one pair of shoes, one pair of knee-high white socks. I do change out my T-shirts and jackets, but I wear the same underpants. I mean, I change them every day, but they're the same kind. I didn't know you could become a style icon by wearing the same underpants.

DP: The best piece of fashion advice I've ever been given is "Less is more." My mom [Robin Wright] taught me that at a young age, so I think that's why I like your sensibility to just keep it simple. I'm all about comfort. When I wear something physically uncomfortable, I become insecure and don't feel like myself. 

JK: I'm actually not completely about comfort, but I wish I was. Even just taking my daughter and son to surf camp in the morning, I like to look a certain way. The other day my friend said, "I've never seen you in shorts." And I said, "Well, that's because I don't own a pair of shorts." Right now I'm interchanging two pairs of blue and black Dickies. There is zero versatility. 

Style Crush Dylan Penn and Johnny Knoxville
Credit: Mark Ralston/AFP/Getty; Hollywood To You/Star Max/GC Images; Brad Barket/Getty Images

DP: I've always been into men's fashion. I had never been complimented on my clothes until I went to my first gay wedding when I was 19. I was the only girl who wore a suit, and all of the gay men bowed down to me. To this day, that's the highlight of my fashion life.

JK: For me, it was when I saw the first wrap dress. I thought, "Thank you, Diane von Furstenberg. Life-changing!" [laughs] I don't know how much I follow women's fashion, quite honestly. I guess I could say I love peep-toe heels, and I'm not a fan of mom jeans.

Style Crush Dylan Penn and Johnny Knoxville
Armani Prive/Dolce & Gabbana/ Chanel
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DP: [Laughs] I would wear anything that Tom Ford designed for Gucci in the '90s. It feels safe to work with labels like Chanel, Tom Ford, and Ralph Lauren. Their sense of how a woman wants to feel shows through in their clothing. Do you have a favorite designer for suits?

JK: I find the red carpet fun — I always try to wear something new and used to go to Savile Row in London on our European press tours. I think it'll be time for a new suit for the Jackass Forever première, but I don't know what that will be yet. I have a lot of Ralph Lauren suits, so I guess that would be my favorite. They're very classic. That's where I fall into, with the classics like Dickies, T-shirts, Converse. I forget what color Chuck Taylors I even used to wear, but once I wore red, I liked how it looked. It's been red ever since, and I don't know why besides the fact that I'm a little OCD. 

DP: That's fair. I collect old crewneck cable-knit sweaters from early in Ralph Lauren's career. They're men's but look so good on girls in a small size. My friends and I trade colors.

JK: I'm strangely attracted to vintage beer sweaters — I search for them on the World Wide Web. I like my white Michelob one a lot, and my red Coors one is pretty good too. Most of my T-shirts are also vintage, but I'm not telling where they're from. Whenever I find a good place for T-shirts, I put that on lockdown. I'm really secretive. 

Style Crush Dylan Penn and Johnny Knoxville
Credit: D Dipasupil/FilmMagic; Larry Busacca/Getty Images; Stewart Cook/Shutterstock

DP: I get it. It's cool to make something your own. It's also great to take risks, but that can be tough. To promote Flag Day I've been working with a stylist for the first time, Rachel Zoe. She encourages me to leave my comfort zone.

JK: I've never hired a stylist. I don't have anyone to turn to, really. [laughs] I just kind of wing it for photo shoots and hope they like the four things I brought along from my closet. So far it has worked out. I don't know whether it's ignorance or arrogance; probably somewhere in between. I'm not sure whether my style has evolved or devolved, but I do wear more suits these days, and I got sick of dyeing my hair, which I've done since my 20s. Finally, I said, the hell with it. That's my style approach now.

Style Crush Dylan Penn and Johnny Knoxville
Valentino/ Louis Vuitton/ Chanel Haute Couture
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For more stories like this, pick up the October 2021 issue of InStyle, available on newsstands, on Amazon, and for digital download Sept. 17th.