Prada boots; Land of Women slip dress.

Photographs by Robert Nethery, Styled by Nora Milch; Manicure by Michina Koide for Chanel at Art Department; models: Anna Z at NY Models, Valery at Parts Models, Samara Oliveira at Major; photography assistant: Juan Carlos Zorilla; Fashion assistant: Devon Head

As we approach the transitional month of September, it's time to revisit Rihanna's style from March. It was during that seasonally sensitive month that the musician and fashion designer stepped out in a daring pair of glittery slouchy boots straight off the Saint Laurent runway, where they'd just made a polarizing debut.

As usual, Rihanna was onto something. (And not just because she paired them with the unbeatable combo of an oversized leather biker jacket and a Patti Smith shirt by Raf Simons.) The fashion industry is now more obsessed with the early '00s than ever, and, as another seasonal change approaches, there seems to be no better technique to sneakily update your wardrobe than simply pairing a dress—or shorts, skirt, whatever you please—with a pair of boots.


Nina Ricci boots; Olivier Theyskens dress.

Photographs by Robert Nethery, Styled by Nora Milch

Of course, those shoes don't necessarily have to reach thigh-high levels—though as Britney Spears showcased earlier this week, if you're looking to give people something to talk about, those'll definitely be effective—or paired with short shorts, as Kate Moss has long been known to do at Glastonbury, and wise aspiring Angels wore to the Victoria's Secret fashion show castings this week. Take, for example, Alexa Chung's approach: While the British It girl is never one to shy from a thigh-skimming dress, she's also been equally known to pair said dress—or jorts, or romper, or jeans—with a pair of boots, ranging from lace-ups to plain old Chelseas. (It's only a matter of time before that approach turns up in her new fashion line, too.)


Sergio Rossi boots; Victoria Beckham dress.

Photographs by Robert Nethery, Styled by Nora Milch

And, other than the fact that she's a well known street style arbiter, you know Chung's really onto something when the pairing has not only long been a favorite of the coolest girl in town for 20 years, Chloë Sevigny, on both the red carpet and the street, but has also become a newfound signature move of one of Hollywood's most stylish emerging starlets, Millie Bobby Brown, who recently showed up to the MTV Movie and TV Awards in a long-sleeved dress and cowboy boots.

Her look may have seemed bold at the time, but it's already looking like, comparatively, Brown was actually playing it safe: Cowboy boots are nothing compared to what may next be the next coolest boots in town. Thanks to Kyle MacLachlan and Kim Gordon, of all people, as well as Chung herself, Uggs are now once again having a moment—and once again proving that all things come back to Rihanna. It was RiRi, after all, who earlier this year also called it that back-to-school looks—yes, including hoodies, logo tees, and more of your former lazy trappings of rolling out of bed and into middle and high school—would soon be cool year-round, too.

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