How Kourtney Became the Best-Dressed Kardashian

Last November, in an interview with James Corden, Kim Kardashian ranked the women in her family according to fashion sense. As she ticked off their names, going from best to worst, I nodded along cautiously.

"OK, best-dressed, I would say Kendall," Kim starts. Sure, I thought. That makes sense, in a safe way. "Second, I'd go for Kris Jenner. Third, Kourtney. No, no, no. Yeah, Kourtney. Fourth Kylie. No, OK, the one before can be Kylie, then Kourtney."

That's where I start to get confused. Kourtney as fourth out of five? Kim, you're bugging.

In the last year or so, I think Kourtney has emerged as the most original and daring aesthete in the Kardashian gang. Every time she wears something new I find myself trolling one of those creepy, celebrity style K-holes, considering a knockoff version of some already-sold-out voluminous top that only looks good on famous people.

And I'm not alone.

A recent Cosmopolitan headline read: "Nothing to See Here, Just Kourtney Kardashian Killing It in a See-Through Skirt." People lauded her "bold style statements" during a recent trip to Tokyo.

But is it a post-Disick wardrobe reboot? A newfound appreciation for vintage? I had to find out what—or who—was responsible for the streak.

"I really don't give many interviews at all," says Dani Michelle, a Los Angeles based stylist who has been working with the 38-year-old Kardashian since January 2017, when we finally connect after weeks of emailing. She also dresses Real Housewives of Beverly Hills star Erika Jayne, The Hills alum Kristin Cavallari, and actor Edgar Ramírez.

"Styling is a relationship you have with your client when two creative minds collaborate with each other and express themselves through clothing," she tells Glamour. "We make looks, edit, and adjust until we're happy."

Sure, but I want details. So I send over a link of Kourtney in the two-piece denim suit she wore on a recent trip to Tokyo—a highlight from a Kardashian vacation's worth of #OOTDs. "This was a vintage Alexander McQueen outfit from 1992 that we found and knew we had to have," Michelle writes back. "It really embodies everything Kourtney’s style is: one-of-a-kind, minimal, with something interesting and cool about it. We resized it, styled it with her Prada boots and a vintage Dior bag, and it was one of the biggest hits of the trip."

The throwback saddle bag was a nice touch—plus, it's evidence of Michelle's affinity for repurposing old classics. "The kit that I keep in my studio is about five racks of clothing and 10 cubbies of organized accessories," she explains. "Sometimes I pull pieces out for fittings or shoots that I have been holding onto for years." (Editor's note: You can find a nineties-era Kate Spade mini nylon bag on eBay for only $22. Just saying.)

I ask about the silhouettes—an RTA fur jacket worn as a dress; high-waisted pants that hit riiight at the natural waist, like a pair of second-skin L.A. Roxx PVC pants worn over fishnet tights—and Michelle nods to her client: "Those famous red pants were the result of Kourtney's vision for this trip overall. She had the idea for custom-making pants from a skirt we saw," she says. "Kourtney knows exactly what she likes, and its my job to help make it happen."

A huge part of that job is paying attention to the smallest details. "For me, the most important pieces to hold onto are bra tops and bodysuits," Michelle says. "When you’re styling with such interesting pieces, sometimes you just need the perfect minimal top to insert into the equation." She pauses and adds, "But granted, with her body, everything looks amazing."

It's true: Kourtney (who has said that she does 100 squats each morning) has never looked better; she's also never looked so confident in her clothes—be it a sparkly kimono, knee-length jorts, or a Matrix-inspired getup. And, in a world where the Kardashian look can be boiled down to a uniform, the originality stands out. Your move, Kimberly.