On the Road with Best Friends Taylor Swift and Karlie Kloss

Taylor Swift and Karlie Kloss have forged the kinds of careers—and the kind of friendship—that people dream about.

One of the first things Taylor Swift did after moving from Nashville to her sprawling two-story penthouse in New York’s Tribeca was cover a wall of her den with framed, blown-up Polaroids of the most important people in her life. “This is when me and Karlie first met,” she says, pointing to a picture of her grinning and hugging model Karlie Kloss backstage at the 2013 Victoria’s Secret Fashion Show, where Kloss walked the runway in pink underwear and giant psychedelic wings and Swift performed with Fall Out Boy. The caption, handwritten in Sharpie, reads BEST FRIENDS FOREVER VS2013 and feels rather prescient given how close the two have become over the past year or so, with a road trip to Big Sur (dreamily documented on Instagram), restaurant outings, shopping excursions, sleepovers, texting marathons, ModelFit and SoulCycle sessions, and a second joint VS outing late last year in London, where, as the pair walked side by side down the runway in black lace, they exchanged “Can you believe this?!” grins—two friends on top of the world.

Lena Dunham and Cara Delevingne also make the Polaroid wall, as does Swift’s younger brother, Austin, 22, a senior at Notre Dame, standing next to his sister in the matching red plaid adult onesies she bought for her family last Christmas. A Polaroid captioned squirrel invasion documents the first time Swift met Lorde (whom Swift calls by her given name, Ella), as the two set out for dinner at Shake Shack in Madison Square Park only to be attacked by rodents. “We were taking these photos, and all of a sudden, like in a horror movie, there were squirrels sitting on our shoulders trying to eat our food,” says Swift, reenacting the moment. “Perched, like parrots! They’re like, ‘We deserve French fries, and we’re going to take them from you.’ ”

Taylor Swift vs. Karlie Kloss—Who's the Best, Best Friend?

Swift click-clacks through her kitchen to her living room in black stiletto Louboutins, plops down on a burnt-orange velvet sofa, wiggles into a slouch, and props those heels up on a tufted brown-leather ottoman. Everything in the apartment is rendered in velvet, leather, and wood in dark, rich earth and jewel tones, from her rosewood Steinway grand piano to her pool table (where VS models Behati Prinsloo and Lily Aldridge apparently proved themselves to be quite the sharks when they came over earlier in the week).

It’s two days before her twenty-fifth birthday, and Swift is brimming with the confidence of a young woman who’s come into her own. It’s been quite a year: She not only moved to New York, away from her family; she’s also taken risks with her sound, stepping back from the world of country to embrace the throwback purity of eighties pop—with amazing success. “Blank Space,” a defiant (and impossible-not-to-sing-along-to) response to the media’s depiction of her as a crazed man-eater, enjoyed a seven-week run atop the Billboard Hot 100. Swift also became the first female in the chart’s 56-year history to replace herself at No. 1 (her earlier single was the now-ubiquitous “Shake It Off”). Both are from her remarkable new album, 1989, named after the year she was born, which has sold more than six million copies and become, along the way, the fastest-moving rec­ord of the past decade. Saturday Night Live, meanwhile, aired a parody commercial for Swiftamine, a drug to treat the epidemic of vertigo in adults who suddenly realize how much they love Taylor Swift. “People are finally starting to discuss her artistry—how she’s on the level of some of the great all-time songwriters,” says Jack Antonoff of the band fun., who’s co-written several songs with Swift and likens her deeply personal storytelling to new chapters of a book the whole world wants to read. “The other day my grandmother was asking me about 1989. We’re all talking about it. In my lifetime, I haven’t experienced that since Michael Jackson—that one artist who stands above and unites us all.”

Swift has also remixed her personal life. For starters, the once-hopeless romantic who laid her emotions bare in songs about whirlwind love affairs and their aftermaths, like “We Are Never Ever Getting Back Together” (reportedly about Jake Gyllenhaal) or “I Knew You Were Trouble” and _1989’_s “Out of the Woods” (reportedly about Harry Styles), is pushing back at critics who have dismissed her as boy-obsessed. The tongue-in-cheek “Blank Space” video shows her stabbing a heart-shaped cake with a butcher’s knife, setting a boyfriend’s clothes on fire, and taking a golf club to his gorgeous silver sports car. Kloss, Dunham, and Delevingne, meanwhile, are part of a close-knit group of powerful women friends that Swift has been building over the past few years. Members also include Selena Gomez, whom Swift has known since they were both teenagers dating Jonas brothers; Jaime King, a kind of Earth Mother figure; and the Haim sisters, whom she met last fall. Devoting this much time to her female friendships started out as a reaction, Swift says, “to the way people were overreacting to my life. I was really irritated by the whole serial-dater play that people tried to make about me.”

She responded by pulling the plug on her love life. “I just decided I wasn’t willing to provide them that kind of entertainment anymore,” she says. “I wasn’t going to go out on dates and have them be allowed to take pictures and say whatever they wanted about our body language. I wasn’t going to sit next to somebody and flirt with them for five minutes, because I know the next day he’ll be rumored to be my boyfriend. I just kind of took the narrative back. It’s unfortunate I had to do that. And it’s unfortunate that now I have this feeling like if I were to open myself up to love, that would be a career weakness.” Instead, Swift is emerging as a powerful figure for teenage girls and young women—someone who takes to task critics and bullies and, yes, men who’ve wronged her, and provides a shining example of a woman shaping her own destiny.

“This last year has felt very different than any other year of my life,” Swift tells me. “I’ve felt more settled and unapologetic about who I am and what I stand for. I think that might be one of those symptoms of growing up and becoming your own person, and depending less on other people’s opinions of you. I just hope that keeps going—because I’m liking it.”

Swift is describing her philosophy about making friends—basically, wear ’em down till they like you—when Kloss sweeps into the apartment, a six-foot-one beam of sunshine. Though Swift and Kloss have known each other for only a year, their best-friendship, they tell me, was instantaneous. They’re a striking pair, particularly now that Kloss’s formerly tawny hair is blonde. “When I did SNL they both came, and at the after-party it was so confusing to everyone, like these Amazon twins,” says Dunham. “Taylor’s so tall, Karlie’s even taller, and together it’s just surreal.”

If Swift wears heels and Kloss wears flats, they’re the same height. But today, Kloss has messed up the equation by wearing skintight Tamara Mellon leather leggings with boots attached. “All-in-one, baby,” she says, showing them off as she walks the floor bearing a tin of her gluten- and dairy-free Karlie’s Kookies, from her collaboration with Milk Bar.

“They’re kind of the greatest thing I’ve ever seen,” Swift gushes. “You look like Catwoman!” Kloss says they’re custom-made, but she can hook Swift up with a pair. “They’re pretty good,” says Kloss, “but I can’t take them back to St. Louis. When I go home, if I have even an ounce of New York attitude, my family’s like, ‘Nope, nope.’ They don’t let it happen.” “They’re like, ‘You with your shoe pants, you leave those outside!’” says Swift, laughing. “You put on some real pants!”

Though Kloss seems to have a keen awareness of every stitch of fashion she has on her body, when I ask Swift who made her black knit tank dress, she has no idea.

Kloss notices the dress, too. “What is this? Alaïa?”

Swift turns to me for help. “I don’t know—do I have a tag in there?” she asks, lifting up her fluffy fair hair and leaning her back toward me. rvn, the tag reads. “My stylist put it in my closet,” she says, burying her face in her hands.

Somehow, though, despite their differing levels of fashion expertise, they often tend to dress the same. “The other night I came over,” says Kloss, “and we were both going someplace from here, and we were both wearing black crop tops and high-waisted skirts. It’s kind of getting weird.”

“Black tights, hair done the same way,” says Swift. “Just like, ‘Ugh, be more annoying.’ We couldn’t possibly be.

“People had been telling us for years we needed to meet,” she adds. “I remember makeup artists and hair people going, ‘Doesn’t she remind you of Karlie? God, she and Karlie would be best friends. They’re the same. Karlie’s such a good girl. She brings us cookies every time we do a shoot.’ ”

“Still do,” says Kloss. As a teen she made them from scratch. Now she makes them professionally—Karlie’s Kookies raises money for charities like FEED, Hurricane Sandy relief, and the CFDA. In addition to the baking venture, Kloss has studied at Harvard Business School (her boyfriend of two years, Joshua Kushner, an early investor in Instagram who recently cofounded the health-care start-up Oscar, is an alumnus) and is now learning computer coding.

A mutual friend, Kloss’s fellow VS model Lily Aldridge, introduced her to Swift, “and we were just like, ‘You. My friend. Now,’ ” says Swift. A few months later they saw each other again at an Oscars after-party, and Kloss suggested they do something spontaneous. “I’d been to Big Sur once before, and I was like, ‘We should just do it,’ ” says Swift.

They walked beneath the redwoods, ran on the beach at sunset, took a picture hanging off the state-park sign with Kloss wearing Swift’s sweater, the front of which spelled out genius. “It’s ironic, clearly,” Swift is quick to add.
When I ask what they bonded over, they shrug. “We’re both normal people,” says Kloss.

“We’re real girls,” says Swift, who, as if on cue, drops part of the cookie she’s eating on her dress, picks it up, and eats it. “Five-second rule.”

Swift is, by all accounts, an amazing person to be friends with. She cooks, she bakes, she does the dishes; she’s a fantastic host, she gives great gifts. She has a collection of old-timey nightgowns that she and her friends wear while watching television and—technology aside—pretending they’re living in frontier days. (Swift, who shows me a picture on her phone of her, Cara Delevingne, and Kendall Jenner all lying in her bed looking like Little House on the Prairie, inspired Dunham to start her own collection.) Every hang, it seems, ends in a dance party in her kitchen. Dunham calls her “the Betty Crocker of friendships” and says she’s most impressed by how Swift always has time for the people she loves. “It’s amazing to have a friend who’s that busy and also so available,” says Dunham. “Even if she’s in Hong Kong on tour and I’m going through something, if I text her, I get an answer in two seconds. If something good happens to me—say, I get a nomination, or it’s my birthday, or the day before my birthday, or my book comes out—I get a text from Taylor way before I get a text from my mom.”

Some of Swift’s eagerness to make friends probably comes from her having felt like an outcast while growing up. “I have lots of issues from school,” she says. “You can tell, probably.” Essentially, she left the small Pennsylvania town where she was made fun of for her music and formed a close community where she’s now surrounded by people with similar talents and creative ambitions. It’s a kind of high school do-over in which she can join whatever clique she wants—or decide to abolish cliques altogether. When I ask Swift which metaphorical lunch table she sits at now, she immediately gets what I’m saying. “I want to make the table as big as possible, and I want everyone to sit with me,” she says.

The next day at _Billboard’_s Women in Music Awards luncheon (where Aretha Franklin sings her an impromptu “Happy Birthday” that Swift later tweets will take her decades to recover from), she sings along to every song, from performances to montages—she knows the words to everything. If female musicians are supposed to all be out for one another’s blood, it’s not happening on Swift’s watch.

Every kid in the room who comes up to her, meanwhile, gets not only a selfie but a conversation. “Little children! I must attend to them,” she says, apologizing for running off in the middle of a conversation. An eleven-year-old girl sheepishly tells Swift she’s from New Jersey. “I spent the summers going down to the Jersey Shore,” says Swift and poses for four apparently blurry selfies before gently taking the phone from the girl’s hand. “You’re really bad at this,” Swift jokes, taking the photo herself. The girl is going to be at Z100’s Jingle Ball concert, where Swift is the closing performer, that night. “I go on really late,” Swift warns her. “Do you drink coffee?” The girl says she drinks Frappuccinos. “OK,” says Swift, “drink a Frappuccino and you might be able to stay awake long enough to see me.”

“New York City, it’s good to be home! I’m Taylor,” says Swift. It’s shortly before midnight, and she’s standing onstage at Madison Square Garden addressing a screaming crowd of 17,000 as if she’s talking to one of her girlfriends on the phone. Dressed in red plaid high-waisted pants and a matching crop top, her hair feathered like Blondie-era Debbie Harry, she blazes through four hits before announcing that she has officially turned 25. “I know why you choose music—it’s because you want to escape from haters and frenemies,” Swift tells the crowd, instructing us to exchange nods of solidarity with our neighbors. “This is the last song of the night,” she continues. “No one’s gonna judge you for how you dance during this song. New York City, are you ready?” The place goes nuts.

Swift returns to her apartment well past midnight, orders sushi, and sets up a makeshift photo booth to host what seems like every famous person in music. She has invited all her fellow performers (Iggy Azalea, Charli XCX, Ariana Grande, Sam Smith, Nick Jonas), along with other friends ranging from Kloss to Abigail Anderson—Swift’s best friend since freshman year of high school in suburban Hendersonville, Tennessee—to Justin Timberlake and Jay Z and Beyoncé. “I have, like, 20 different people flying in,” Swift had told me the day before. “My friends are staying in every room.” Her mother, Andrea, however—who flew in from Nashville earlier laden with decorations now draped over mirrors and mantels, with every window in the place (I lose count at fifteen) garlanded as well—isn’t there. “I think a twenty-fifth birthday, no mother should be there,” Andrea told me. “You need to know when to step away.”

The next time I catch up with Swift, she’s still in her PJs at 11:15 on a perfect sunny January morning at her house in Beverly Hills. In the month since I saw her turn 25 she’s become the proud owner of a bejeweled necklace (a birthday gift from Dunham) bearing the image of her kitten Olivia; danced like crazy with Beyoncé and the Haim sisters at a Justin Timberlake concert in Brooklyn; bought the shirt off Hugh Jackman’s back (giving $6,000 to the Broadway Cares/Equity Fights AIDS charity in the process) while seeing him perform on Broadway with her family; sent out a large batch of gift packages to her fans, one of which included a Swift painting of flowers and a check for $1,989 to help pay off a student loan; and rung in the New Year onstage in Times Square in front of a million people live and a billion more on TV and the Web. Since she’s been out West, though, she’s been doing what she can to catch up with friends, including “a lot of cooking nights,” hiking with Lorde, and wandering around Catalina Island eating ice cream with her girlfriends and her dad. When Lorde sounded stressed about going to the Golden Globes, Swift showed up in support wearing a bright-yellow dress (in honor of Lorde’s nominated song, “Yellow Flicker Beat”). “We just turned it into a girls’ night,” Swift says over the phone.

For both today and the foreseeable future, though, Swift is going to be all business getting ready for the 1989 world tour, which kicks off May 5 in Tokyo. There’s a set list to finalize, and wardrobe and production design to approve, and choreography to learn. She insists she’s not nearly as awkward a dancer as she pretends to be in the “Shake It Off” video: “If I get serious about choreography, I will learn it and I’ll do it correctly—most of the time,” she says.

Looking back on what’s been both a tumultuous and momentous time in her life, Swift says she and her family “had a lot of moments where we would look at each other and say, ‘Wow—I can’t believe people got it.’ You only hope for things like this.” She’s been trying to take it all as it comes. “I don’t get so caught up in the work that I don’t appreciate the crazy, incredible, astonishing, joyous success that’s happened,” she says. “Putting pressure on yourself is good, but putting unnecessary stress on yourself is bad—so I don’t worry that I haven’t started the next record yet. I don’t worry that I don’t know what it’s going to be. I’m not worried that I have absolutely no timetable as to when it needs to be done. It could be two years from now; it could be three, it could be four. Or it could be one. You get these bursts of inspiration right at the moment you’re not expecting to. You just have to live your life, and hopefully you’ll take the right risks.”

Kloss, for her part, has been maintaining the kind of schedule that would seem to require its own air-traffic controller. After a short break back home in St. Louis, she’s been back and forth to Paris twice in early January alone as part of her new job as a L’Oréal Paris spokesperson; to the Florida Keys for a Bruce Weber shoot; and to L.A. and Paris again for L’Oréal. Next up: back to L.A. for the Oscars before ramping up for Fashion Weeks in New York, Milan, and Paris. “In moderation it can be really fun,” says Kloss, who’s cut the 60 shows she used to walk at the start of her career down to a fraction of that. “For me, runway is an opportunity to perform.”

She’s also practically bursting to tell me some big news: She’s been accepted to NYU’s Gallatin School of Individualized Study. (NYU alum Christy Turlington Burns wrote her letter of recommendation.) “I was waiting for the mail to arrive every single day,” she says. “It’s something that I’ve wanted to do for a very long time.” Kloss doesn’t yet know what she’ll study; for now, she’s just excited to be taking classes. “I’ll still be working full-time,” she says. “I’m incredibly ambitious and have lots of goals within my career that I’m not slowing down on anytime soon.”

Swift says she and her friends don’t talk much about work. “The fun thing about my friends is that they don’t necessarily know a lot about what I do business-wise,” she says. The first time Kloss ever saw Swift pick up a guitar and noodle around on it was during the photo shoot for this story. “I’m not one of those singers who’s always like, ‘Look at me!’ ” says Swift. “I’m not the person who grabs the guitar at a party and wants all the attention. I have attention on me enough, so I want my friends to just like me because we have things in common rather than me sitting in a corner being like, ‘Listen to this song that I wrote about my life!’ ”

No matter how busy they are, though, Swift and Kloss continue to make time for each other. Swift recently had Kloss over to her place for a night of cooking pasta with model Martha Hunt, stylist Ashley Avignone, and Tavi Gevinson. A few days later that same group went to dinner at Ralph Lauren’s restaurant, the Polo Bar, in midtown. (“The French fries were delicious,” says Kloss.)

Kloss says that bringing together disparate women from different industries may be Swift’s most unsung talent. “I’ve met a lot of really great girls through Taylor. She’s incredible at connecting people who might not normally meet. We’re all in different jobs, but we’ve become strong friends who are there for each other—a sisterhood of girls, a support team. But we’re also just normal 20-something girls, and I think you have to have people that you can be that with. You know, real friends are hard to find—and Taylor’s a real friend. There’s nothing better.”

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