Talking Fashion With Ben Stiller and Ansel Elgort

Who's getting a cameo in 'Zoolander 2' (if it ever happens)?
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Who's getting a cameo in 'Zoolander 2' (if it ever happens)?
Matthew Orley, Samantha Orley, Ansel Elgort and Alex Orley at the CFDA/'Vogue' Fashion Fund dinner Monday night. Photo: Theo Wargo/Getty Images

Matthew Orley, Samantha Orley, Ansel Elgort and Alex Orley at the CFDA/'Vogue' Fashion Fund dinner Monday night. Photo: Theo Wargo/Getty Images

You go into an event hosted by Vogue and the CFDA expecting it to be a who's who of the fashion industry — which it was. But, sometimes big Hollywood stars show up, too, wearing clothes designed by those present. 

On Monday night, I found myself in the same room as legendary editors, supermodels, top designers and some of my favorite actresses (Greta Gerwig, Gillian Jacobs and Jenny Slate) and actors, including the irrefutably dreamy Ansel Elgort and irrefutably funny and smart Ben Stiller.

When I saw the latter two posing for photos in a corner with perennial fashion party attendee Joe Jonas, I made my move.

Elgort, whose father is legendary fashion photographer Arthur Elgort — and who appeared in Vogue countless times as a child and made a recent cameo in the October 2014 issue alongside Andreea Diaconu— says he isn't that into modeling despite his experience doing it ... and his physically looking like one. "I was so young, I didn’t really think anything of it. My dad was kind of like, 'Can you be in the background of this picture?' And I would just go." These days, he sees modeling as a vehicle to promote his movies. "I wouldn’t like to be a model to be honest, I’m more into acting." Regardless, he is tall, handsome, and wears clothes really, really well. In this case, it was a fisherman-like cream sweater and white pants (a tough look to pull off) by buzzy menswear brand and CFDA/Vogue Fashion Fund finalists Orley.

Stiller, too, has an important tie to fashion, and that would be "Zoolander," the second installment of which has been rumored to be happening for several years now. However, the film is not as much of a sure thing as recent reports have suggested, Stiller tells us. "I know people keep on saying it’s coming together but it has not come together yet." When asked if he could say for sure that it would happen, he said, "I would not say that." But, he did say, "it’s as close to happening as it’s ever been and I think soon we’ll have a resolution." 

Beyond that, Stiller says he could never have expected the film to have such longevity. "I just ran into Joe Jonas who [was Zoolander for Halloween]! When the movie came out, it wasn't particularly successful and there are very few experiences like that where it has a life afterwards. In a way it's a lot more gratifying than a movie that's a big hit when it first comes out, so I had no idea and it's really fun to see that it has this life."

We couldn't help but think that the room Monday night was full of potential "Zoolander 2" cameos. While Stiller wouldn't name names (Cara Delevingne has been rumored), he said "it's safe to say" there will be surprise fashion industry appearances if the flick does happen. Wait — could that have been why Stiller was there in the first place? "I just got an invite from Anna Wintour," he explained, "and you don't say no to Anna."

I think we've figured it out: Wintour herself is angling for a role in the "Zoolander" sequel. We can't wait to see this movie.