By Jennifer Ferrise
Updated Jun 12, 2018 @ 9:00 am
Credit: Photo Illustration. Photo: Getty Images

When it comes to nailing that impossibly chic off-duty model look, no one does it better than Joan Smalls. From camo bomber jackets with newsboy caps to cut-offs and suede over-the-knee boots, the 29-year-old Puerto Rican stunner has perfected the art of effortless street style, when she’s not walking runways for Balmain, Moschino, or Tom Ford, that is.

And while we’re pouring over her every single mix-and-match, it turns out that Smalls has been drawing outfit inspo from her own supermodel style crush: Rosie Huntington-Whiteley.

“Rosie’s style is always effortlessly sexy,” says Smalls, who has been pals with Huntington-Whiteley for about six years after they met at a birthday party. “She’s never trying too hard. When you look at her, you just see Rosie. Her street style is always put-together and still so cool. And whenever you see her on the red carpet, she has this aura around her, consistently pulling off things that other people couldn’t.”

And as for Huntington-Whiteley? The style crushing is mutual (“I wish I could look like Joan!” she says). So for our July issue, we connected the two besties to talk shop. On the agenda? Red carpet disasters, wearing couture to get coffee, and the secret to looking good without any makeup (hint: huge sunnies!). Read on for their full chat below.

JOAN SMALLS: When we met, Rosie, I thought, "This girl is a sexpot on heels. And so funny too!" It was love at first sight.

ROSIE HUNTINGTON-WHITELEY: We're both cheeky! And thanks for picking me as your style crush, by the way. I'm so flattered.

JS: You can pay me later!

RHW: I will. I clearly remember meeting you for the first time. We both got invited to Derek Blasberg's birthday party about five or six years ago and the theme was The Party, the movie from the ‘60s with Peter Sellers. I put this sort of ‘60s swinger outfit together really last minute, but when I got to the party everyone else was much more mod, so I was like, ‘F—uck, I didn’t get the theme right. When we met, you were like, “What did you come as?” And as soon as I started talking, you were like, “Fail!” Teasing me from the start. And that was the beginning of our friendship [laughs].

JS: That’s right! And I was like, ‘Oh my god, she understands my humor.’ [laughs] I remember I was wearing a Marc Jacobs checkered short skirt and this plaid vest.

RHW: You looked amazing, obviously.

JS: You always look great. I love that your style is effortlessly cool. You never try to look like somebody else.

Credit: Raymond Hall/Getty Images

RHW: I wish I could dress like you: off-duty, tomboy chic. Our style is totally different though. Your look is always more relaxed. When we were working with each other a few weeks ago, you would walk in every day and with a cool leather jacket or a cool pair of jeans. I think our biggest difference is that I’m always in heels and you like to wear flat shoes.

JS: I was going to say that too!

RHW: I nearly stole your Alexander Wang fanny pack the other day, you know.

JS: You wanted my Louis Vuitton boots too!

RHW: I almost bought them, but I wouldn’t look as good in them. You’re long and gazelle-like, so you can get away with flat shoes.

JS: By flat, you mean a two-inch heel [laughs]. You know my closet is full of boots—what is yours full of right now?

RHW: Blazers. I have a million. You can put them with something simple like jeans and a t-shirt and still feel so polished.

JS: Is your closet a mess like mine? I know where everything is, but it’s still a mess.

Credit: Gotham/Getty Images

RHW: Mine is organized chaos. I’m always at the brink of having no space. Every six weeks, I go through and take out what I’m not wearing for storage or to give away. I think I gave away three racks the other day.

JS: Oh my God!

RHW: I still go in there everyday and think, ‘What am I going to wear?’

Credit: Stuart C. Wilson/Getty Images

JS: My biggest problem is that it’s hard to part with classic items. I hold onto things that I think I’ll wear again. Rosie, have you ever worn something that you really regret?

RHW: I had a black gown that ripped up the side at an event in Vegas. We were walking through the casino and found a store that had a tailor, so we begged him to fix it! My makeup and hair was a disaster too. It looked like I stuck my finger in an electrical socket. It was the night I met Blake Lively, of course [laughs]. And we had our picture taken together.

JS: Still, you never look bad. My favorite look of yours was that red Antonio Berardi suit [above]. You had these glossy red lips to match and your hair slicked back. Total boss bitch.

RHW: Your purple Cavalli [below] at the Met Ball was my dream dress. You always nail it at the Met Ball though.

Credit: Larry Busacca/Getty Images

JS: Not my first year though…

RHW: Oh, I don’t remember you looking bad. Everyone has to find their sea legs with the Met Ball.

JS: Aw, thanks! What designer would you call to make you a dress in a pinch?

RHW: Anthony Vaccarello. I’ve been friends with him since his very first collection. And then I’m a big, big fan of everything he is doing at Saint Laurent. He’s amazing at cuts and the looks are always very sexy, tough, and rock and roll. I always feel empowered in his looks.

JS: Do you get a discount now?

RHW: Hell, yeah! [laughs] Who would you pick?

JS: Riccardo Tisci. When he was at Givenchy, I would wear his stuff religiously because it’s my style. That femme fatale thing that I always look for. He knows my personality so well too, it’s like second nature. OK, pick one: never wearing heels or never wearing makeup?

Credit: Alessio Botticelli/Getty Images

RHW: For the rest of my life?! Never wearing makeup, I guess. I love heels too much. There are ways to get around not wearing makeup and still looking good.

JS: Big sunglasses?

RHW: Yes! Exactly.

JS: You're almost always in heels. Do you have a favorite pair?

RHW: My Alaïa boots. I'll never part ways with them. Never. I was horrified because after I had my baby, my feet didn’t go back to the same size right away. I thought I was going to have to get rid of all of my shoes, but thankfully, they kind of went back.

JS: You’ve been working out your feet. [laughs] What's the fastest time you can do your makeup?

RHW: I can do a five-minute face: tinted moisturizer, cover-up, glue my eyebrows down, curl my lashes, bronzer, and blush.

JS: That sounds longer than five minutes.

RHW: It's probably 15. Maybe that's why I'm always late.

JS: Ha! Do you ever wear shorts? I've never seen you in a pair. You know I love them.

Credit: Jacopo Raule/Getty Images

RHW: Well, I just had a baby, and my legs aren't up to scratch yet. I feel too exposed in shorts. It's the English girl in me ...

JS: What body part do you like to accentuate? Your butt is great.

RHW: You think so? I'm a sucker for a backless dress. It's sensual, and it's always, like, party in the back! What about you?

JS: Legs, for sure. What's the best thing you've kept from work? I’ve got tons of shoes that I’ve kept from runway shows. And I just got this cute T-shirt from my movie, Set It Up.

RHW: Oh yeah, remember when they used to let you keep the shoes from the shows? Not anymore! I was lucky enough to keep a few Versace gowns that Donatella made for me though. I have them wrapped in tissue and stored in airtight containers. Not sure what I'll do with them now.

Credit: Taylor Hill/Getty Images

JS: Uh ... do we have the same measurements [laughs]?

RHW: You can wear them to go get coffee if you want.

JS: Finally! I can tell everyone that I'm wearing vintage Rosie.

Joan Smalls stars in Set It Up, streaming on Netflix on June 15. Check out the trailer above. And for more stories like this, pick up the July issue of InStyle, available on newsstands and for digital download now.