Olivia Rodrigo Posed With Alanis Morissette in a ’90s-Inspired Slip Dress

There’s something so effortlessly cool about a slip dress. It’s the kind of trend that doesn’t have to try too hard, making it a quintessential staple in any It girl’s closet. Olivia Rodrigo styled hers in true Y2K fashion at the Canadian Songwriters Hall of Fame Gala, featuring a white satin slip with black lace trim, delicate black lace detailing across the bodice, and a matching lace choker. She paired the slightly vampy look with a bold red lip and wore her dark hair all the way down with small braids throughout, giving the lightweight silhouette of her outfit more autumnal energy.

The gala took place at Massey Hall in Toronto, where Rodrigo had the honor of inducting the iconic singer-songwriter Alanis Morissette into the Hall of Fame later that night. Seeing as she was there to pay tribute to one of her biggest musical inspirations and a true queen of the ’90s pop–rock scene, it makes sense that Rodrigo stepped out in a look with a nostalgic feel to it. In fact, this might be the very reason for details like her lace choker, mini braids, and grungier makeup, which feel a little bit edgier for Rodrigo, especially when compared to her typical trendy aesthetic.

That being said, we have seen her experimenting with her fashion lately, staying true to her Y2K roots but gravitating towards more alternative pieces with velvet corsets and dark academia-inspired outfits. Morissette herself stood out in a full red suit with a colourful patterned blouse and glittering heels, and the two posed together for the first time since their cover on Rolling Stone. Check out the details of Rodrigo’s nostalgic ’90s-inspired look below, and see how she’s making the trends of the past feel new again.