You Oughta Know: Alanis Morissette’s Style Evolution

Fresh-faced and glowing from her sudden rise to fame with the 1995 release of Jagged Little Pill -- her third album, but first major hit -- Alanis was all about oversized-everything. While she might be drowning in fabric in her choice of outfit for the MTV Video Music Awards in 1995, we have to give her props for being ahead of the times with her less-is-more beauty look and leather pants.

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For the 1996 Grammy Awards, Alanis opted to forgo the usual baggy-fit pants look and go for a slightly more glam style. She kept her signature boho beauty look, but stepped out in an unexpectedly-feminine sating floor-length dress, which she styled under a leather jacket. While it may not have been the most flattering fit, the look was a clear indicator that Alanis was open to broadening her style sense, and still honing in on her fashion identity. The night was a win overall, however, as Alanis took home the hardware for Album of the Year.

Fun fact: Alanis’ hit song “You Oughta Know” is said to have been inspired by one of her 90’s boyfriends, actor David Coulier — if you’re wondering where you know that name from… this is the actor who played Uncle Joey on Full House!

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Elevating her red-carpet style in a big way since her 1996 appearance, Alanis Morissette stepped out for the 1999 Grammy Awards in a sparkly, beaded gown and matching shawl, looking every bit the bohemian princess with her signature wavy, long locks and minimalist beauty look.

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Performing for the launch of her album, Under Rug Swept in 2002, Alanis stuck to her signature leather-pants-and-concert-tee style, but swapped out her loose waves for some mega-crimped hair instead.

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Everyone’s favourite “remember when” Canadian couple, Alanis Morissette and Ryan Reynolds were the cool couple to be in the early 2000’s — right down to their badass matching leather ensembles — take that, Justin and Britney — leather beats denim every time.

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All tangled up in poor fashion decisions, the otherwise glowing Alanis stepped out for a good cause, and one she’s been vocal about throughout her career, at the 13th Environmental Media Awards in 2003. While she may not have dressed to impress, we’ve never been let down by this homegrown icon’s sense of consciousness when it comes to the things that matter. Slow clap, anyone?

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Having chopped off her signature locks for a short pixie-style cut in 2004, Alanis turned heads at the GLAAD awards that year in a knit blouse, satin skirt and leather boots. We love this more refined red-carpet glam on the singer, who was clearly coming into her own as far as defining her personal glam style.

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Alongside then-fiancée Ryan Reynolds, Alanis Morissette had jaws drop to the floor when she stepped out for the 2004 Juno Awards in a low-cut, orange satin dress and fuchsia neck scarf with matching pointed-toe heels. A total departure from her early red-carpet style, Alanis stunned in this bright and on-trend ensemble.

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Blink and you might have missed her gliding down the red-carpet looking like, well, someone else entirely. Looking almost unrecognizable at the Golden Globe Awards in 2006, Alanis not only went for a light-coloured (and strapless!) gown, but also some seriously lighter locks. Sporting a blonde, seemingly Farah Fawcett-inspired hairstyle, Alanis was all smiles for the event, but we might’ve suggested a gown that didn’t blend so well with her skin tone, risking a slightly too-nude vibe.

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We’ll go ahead and blame the low-rise jeans trend for the unfortunate bottom-half of this getup, but we otherwise love seeing Alanis in this pop of red draped halter-top, worn to Prince's "3121" live at The Hollywood Roosevelt Hotel in 2007. Another one of those unexpected sexy-style moments for the singer, who never found a trend she couldn’t turn boho-chic.

In case you're wondering, The Hollywood Roosevelt Hotel is said to be a haunted hotel you can still stay in.

Speaking of unexpected sexy-style moments — Alanis served up another one during her 2008 appearance on Rosie Live Variety Show, donning a fitted, low-cut, strapless dress and super-sleek, straight hair with blunt bangs.

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Entering what we not-so-affectionately call Alanis’ “vest phase”, the singer began what would be a long period of throwing a vest over every outfit, at all times. Not sure what inspired this super-unflattering fashion go-to, but we’re glad it didn’t last.

Rocking a mini dress with a low, draped neckline, strappy pumps, and soft, wavy hair, Alanis looked all grown up while attending a benefit concert at Club Nokia in 2009.

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We are still not over this drop-dead-gorgeous Alanis look from her 2010 appearance Disney Pictures’ Prince of Persia: The Sands of Time film premiere. Wearing a floor-length black gown with low-cut neckline and bejeweled detail, Alanis absolutely nailed this red-carpet look – all while revealing a hint of a baby bump, pregnant with her first child with husband, rapper Mario Treadway.

Wearing a belted black dress with a high slit and hair sleekly styled in a side-braid, Alanis rocked that “new mom” glow – and brought some arm candy along in the form of her husband, rapper Mario Treadway.

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While attending an after-party for a benefit event in Los Angeles in 2014, the now-mom of two, Alanis rocked a sheer-detail black dress with bright red pumps. We love that the singer continues to have fun with her “glam looks” while still maintaining a sense of the boho-babe signature style she’s become synonymous with.

Giving her beloved leather pants a rest, Alanis got her leather fix in this mock-neck-fishtail-skirt ensemble, worn to the 2015 American Music Awards. While we aren’t sold on the fit, we can’t help but love how much fun she’s been having continuing to experiment with her red-carpet fashion choices.

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There’s not much to say here, other than that none of this ensemble, from the hair to the shoes, makes any sense. Alanis, we love you girl, but fire your stylist. Yikes.

Donning a super-short pixie haircut, Elton-John-inspired glasses and a floaty draped white dress, Alanis and husband Mario Treadway attended a Broadway musical together in 2018. While we’re digging the shorter hair and funky accessories, we’re not sold on the retro eyewear – but you do, Alanis, you do you.

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Possibly our favourite Alanis style moment from 2019 is watching her rock her third-pregnancy glow while speaking on stage for Billboard’s Women in Music event, donning what is possibly her best style look yet. This double-breasted blazer getup is chic, effortlessly-glam and unexpected – which is exactly how we like our Alanis to serve it.

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