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In Honor of the 'Jagged Little Pill' Deluxe Edition, an Ode to Alanis Morissette's '90s Style

The iconic album gets rereleased on Friday for its 20th anniversary.
Photo: Tim Mosenfelder/Getty Images

Photo: Tim Mosenfelder/Getty Images

Regardless of where you were when Alanis Morissette released "Jagged Little Pill" on June 13, 1995 — or, if you were even alive to experience it at all — the album has left an indelible mark on pop culture. Not only did this record propel the little-known Canadian singer and songwriter to rock star status, it's also managed to stand the test of time in more ways than we can count. "Jagged Little Pill" won four Grammy awards in 1996, making 21-year-old Morissette the youngest musician to win Album of the Year at the time. Since then, her disc's best-selling single "You Oughta Know" has been covered by everyone from Britney Spears to Beyonce to, most recently, Taylor Swift, when she welcomed Morissette to the stage during her 1989 World Tour. Morissette's irresistible, guitar-driven melodies haven't gone out of style in the 20 years since the album's epic debut — and neither has her effortless '90s look.

Given her angsty lyrics, it's not surprising that the singer's uniform was a study in contradictions. She favored slouchy staples, usually paired with roomy trousers or leather pants. Think men’s button-ups (which she wore on the cover of Rolling Stone in 1995) and cozy sweaters, like the ones she donned in the famous video for her 1996 single "Ironic." When she wasn't in these oversized pieces, Morissette swung to the other side of the '90s trend spectrum, opting for sheer lace tops and silk slip dresses. No matter what she was wearing, Morissette's long hair has remained her most important accessory. This waist-length brown fringe helped her rock out in the video for "You Oughta Know;" it was buried under a red beanie in "Ironic," and it hung straight, unbrushed and middle-parted in the clip for her third single, "Hand In My Pocket." The result was an understated yet totally cool vibe — because, let's be real, Morissette isn't exactly the type to spend hours getting ready. 

The return of '90s fashion is nothing new; in fact, you could argue that it's never left. But, Morissette's low-key style philosophy has made a noticeable comeback. Androgyny has ruled both the women's and men's runways the past several seasons, both in terms of menswear-inspired silhouettes at labels like The Row or women walking the runway at men's shows like Gucci and Saint Laurent. Models like Lexi Boling and Natalie Westling are nodding back to Morissette's original tomboyish uniform off the catwalk as well, and they even have the long hair to match. Rather than getting dolled up before they go outside, they're unfussy and all-natural – which, like Morissette, makes them even more interesting.

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Although "Jagged Little Pill" first came out in June, Morissette celebrates the album's debut with a Deluxe Collector's Edition on Friday, complete with 10 unreleased demos and a remastered original disc. We suggest you pick it up and get ready to obsess over the singer all over again. Who cares what year it is? Wrapping yourself up in a cozy fall sweater and belting out "You Oughta Know" at the top of your lungs never gets old.  

Watch a couple of our favorite Morissette video moments below.