Alanis Morissette is walking into her closet. She lists off her many sneakers, her shoe of choice: “For the grandma in me, I have all my wide toe box ones that are ugly. I have my female running shoes. Lots of Adidas, a couple Nikes, Balenciaga, and Maison Margiela,” she tells me over Zoom. “And then I love these Dries loafers that are sort of leopard, snake, skinny, interesting.”

Morissette, fashion maven. Who knew? In fact, the “You Oughta Know” singer traces her love of Dries Van Noten back to 1995, the year she unleashed her seminal album Jagged Little Pill into the world to the tune of over 33 million copies sold and five Grammy Awards. That’s the year she started buying the designer’s clothes. 

Morissette’s admiration is coming full circle. Dries Van Noten, now under the creative direction of Julian Klausner, styled all eight of Morissette’s looks — integrating pieces from the Fall/Winter 2025 collection — for her Las Vegas residency at the Colosseum at Caesars Palace, which has its last show November 2.

Three decades after Morissette, 51, redefined rock and how female musicians are viewed, the artist discusses her personal style, ridding herself of ’90s expectations, and what it’s like to be dressed by Dries. 

Dennys Ilic

As a ’90s kid, I never imagined you as a Vegas kind of artist. 

Well, yeah, from the ’90s lens, you can’t do anything but one thing. Out of your lane is career suicide. Whereas I think hopefully, in modern times, it’s more of an invitation to be who you were born to be — who you actually are.

The show is such a multidimensional experience, integrating biography, narrative, comedy, and music. What made you want to go that direction?

I had two years worth of storytelling that I did not want to put in a memoir. I kept saying over and over again, “I don’t want to do a memoir.” Yet somehow I kept showing up for these sessions. I had 97 files of four hours each of stories. I said, “Okay, so we have six weeks to put on a show that ideally would take nine months.” I don’t consider myself an actor, but I know that I can tell stories and that I have a sort of sublimated comedic intelligence. My comedian friends would say, “Oh no, you’re funny.” But I grew up in the patriarchy vibes of women aren’t funny. So that part had to come out.

How did you get into Dries, and what made you reach out to the label to collaborate?

I’m just a fan. A lot of designers in the ’90s reached out to me to hang out or to come on their boat. I was always like, I’m too scared to go anywhere, but I’m not too scared to be an aesthete. The aesthete in me has always been obsessed with Dries, his aesthetic — such a combination of audacity and brazen, but also so subtle and nuanced. It’s for the high-novelty, high-sensation, bombastic part of me. The pattern on pattern on pattern is my dream, and then the excellence and the mastery and the fabric and the combination. But I’ve never met Dries Van Noten.

What? That’s wild. You’re Alanis Morrissette. You can meet Dries.

I would be honored to. But Julian [Klausner] I’ve connected with, and everyone over there is like, wow, dream. They’re all sensitive. 

Dennys Ilic

Your outfits when you were touring in the ’90s are very different from the looks for this show.

In the mid ’90s, it was black, leather, white, very monochromatic. And in the late ’90s, when Supposed [Former Infatuation Junkie] was released, having returned from India, I went through this whole era of saris, all the bright ochre fabrics. I didn’t want to wear a straight-up skirt, so we would cut slits up the side. I would take all these different fabrics and mix them with mesh tops. And it’s almost a 10% glimpse of what was to come for this show. I consider myself androgynous, and some of the pieces for the show were from the men’s line. 

There’s a lot of purple going on. It reminds me of the cover of your compilation album The Collection. 

I see color when I make music and meet people. Every time I’m writing a record, the color purple is used. And how Dries uses it, how the house uses it, how Julian uses it, with the browns and the blues and that indigo and purple — like, wow, it’s my dream.

Can you walk me through some of your favorite looks or pieces?

They’re all my favorites. The burgundy sheen pants that I wore at the last show with the tank top, sequins, mesh. And there was one in a similar print, different color choices, with some really nuanced bedazzle, sort of shimmer on the top shirt. 

I love wearing clothes on stage where I don’t have to be self-conscious. I don’t have to worry about what bits are popping out. I can just focus on the show, focus on the movement, focus on the moment. It looks so elegant and effortless and chic. At the same time, I’m sweating and moving and crawling on the ground and dancing. I’m always saying, “Wear your diamonds with your sweatpants.” Because we’re all gonna die. Pull out the China, you know? That’s how I feel when I’m on stage in these beautiful looks. I feel like it’s the perfect combination of being an obsessed curating aesthete and the messy, dirty hippie, barefoot, ‘What is she doing?’

Dennys Ilic

Dries Van Notes is known for starting with really powerful flower-based prints. What about that speaks to you?

I consider myself a symbologist. Anything to do with flora, fauna, nature, Earth is just such a big part of my spiritual practice. Particularly orchids, which are sort of symbologically tipping the hat to sensitive people, empaths. It’s not a shocker that I’m going to project onto the whole Dries house that everybody there is a sensitive empath.

With the show closing this weekend, what would you say was your favorite moment?

There was a moment where I felt like it became cohesive, where everything made sense. I felt the show become a story. It’s sort of narcissistic by default. It drives me crazy. 

But is it narcissistic if people connect to it? 

I’m offering these 700 things that may or may not trigger you or uplift you or piss you off, or whatever it is. It’s an invitation, really, and it’s a permission. 

What would you tell yourself 30 years ago?

I would say, “There will be a day where you will start to make sense to people.” I think she’d be assuaged by that a little bit, because I thought, I’m just gonna spend this particular lifetime being misunderstood, and that’s fine. It was depressing, but I took it on, you know?