Emily Ratajkowski and Sistine Stallone on Why This Menswear Look Makes Them Feel Sexy

Model Sistine Stallone is no fashion newbie. At 19, she’s walked the runway for Chanel, partied with Sofia Richie at the Met Ball, and been Miss Golden Globe, alongside sisters Scarlet and Sophia, with Dad Sylvester proudly looking on.

And on top of all that, she’s got great style instincts—as one quick scroll through her Insta will prove. But we wondered: Out of everyone she has met in the industry, whose look is she crushing on right now?

The answer was easy: Emily Ratajkowski.

So for our January issue, we connected the two style stars to talk shop. On the agenda? Boot obsessions, mom jeans, and a shared love of Tom Ford. Listen in on their chat below.

SISTINE STALLONE:So, Emily, I love every outfit you post on Instagram. Your street style is so cute—and you wear everything with such confidence.

EMILY RATAJKOWSKI:Aw, I’m blushing [laughs]. I’m a fan of yours too! I loved your shoot for Love Magazine.

SS: Thanks! You always nail it on the red carpet, all the way down to your hair and makeup.

ER: Fashion was very intimidating to me at first, but now I’m like, “Let’s have fun with this.” I always try to balance feminine pieces with things that are interesting and masculine.

SS: I love that. I’m actually really into menswear lately.

ER: Same. I will forever be the most comfortable in a suit with literally nothing underneath it. I never really feel sexy in a pair of tight jeans and a tight top, you know? Boyish, oversize pieces are sometimes the sexiest.

SS: Yeah. I like to do a big jean jacket with nothing underneath and some cool biker boots.

ER: Oh, boots are my thing too! I have a full-on boot problem. The hunt for the perfect one is my lifelong mission, I feel.

SS: That’s so funny! How many do you think you have?

ER: Probably like 10 pairs of just plain black ones even though it’s so warm in L.A. and I don’t really need any. Obviously we're both very lucky because we get sent a lot of stuff, but the one thing I will never feel bad about spending money on is a good pair of shoes. Whether they're from a thrift store for $10 or they're $900, I always know I'll wear them.

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SS: We’ve both worn red boots recently, I think.

ER: Yes! They make me feel like I’m French, and I’m constantly trying to be as French as possible. That look combines three of my favorite things: boots, the color red, and looking French. [laughs] Red is a good color for both of us actually. We have similar olive skin tones.

SS: I like red, but for some reason, I don’t usually go for hot pinks or bright oranges.

ER: Well, color is something that has evolved for me too. My mom was a bit more old school, and when I was younger she taught me not to wear white in the winter and not to mix navy blue and black. With jewelry, I used to never wear both silver and gold. Now it’s completely different. Those rules don’t apply.

SS: I still tend to go for white, black, or silver [laughs]. Like at last year’s Met Ball (below), I wore this awesome sequined silver Topshop gown that made me look like a disco ball. What’s been your favorite recent red-carpet moment?

ER: Probably a Jacquemus look that I got to wear in Paris that was essentially a white shirt made into a super-sexy dress. Jacquemus is a friend and I love that he’s a cool, young designer that’s just doing his thing. I also love basically anything I’ve worn from Prada. Miuccia is a badass. Her clothes are chic and flattering.

SS: That’s how I feel about Tom Ford. Every time I put on one of his designs, it fits so well.

ER: It’s hard not to love Tom, right? He’s an amazing person.

SS: I like vintage pieces a lot too. I raid my mom’s closet when I have nothing to wear because she has so many good throwbacks from the ‘80s and ‘90s.

ER: I think I buy more vintage than I do new brands at this point. There are so many good shops in L.A. and when I was in Paris, I didn't go to any designer stores, I just went to vintage places. I found these amazing Saint Laurent high-waisted pants. There's something special about finding something great in a vintage store—it feels like it’s meant for you. Plus, nobody else will have it!

SS: Yes! In general, would you rather be overdressed or underdressed?

ER: That’s a tough one. I used to say underdressed, and now I’d say overdressed. In L.A. everyone is always underdressed, so it can be really fun to be the one who's walking in with a full look with a little cocktail bag. How about you?

SS: I think I'd probably say overdressed as well. And you can always just say you came from a fancy event—some place way cooler than where you are now.

ER: Totally!

SS: Last question: What’s your go-to casual look? I pretty much collect baggy mom jeans at this point. I do them with a button down and some white Nike sneakers.

ER: Oh, I hear you with the jeans. Vintage Levi’s are the best. I also just wore this striped Prada turtleneck with Adidas sweatpants and felt so great in it. But most days, I’m like most girls who have a closet full of clothes and nothing to wear.

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