I’ve been stockpiling photos of Carolyn Bessette-Kennedy on Instagram as fall style inspiration for months (exhibit A, B, C — I honestly could go through the entire alphabet). Her no-frills approach to dressing seems so distant from mine, which is why I think it resonates with me so deeply: It’s aspirational. I like to fantasize that the true adult version of me will amass a closet full of quality staples just like hers: crisp button-ups, black turtlenecks, timeless blue denim and classic loafers as far as the eye can see.
Carolyn is one of many 90s-era fashion icons I keep in close circulation. I may have been born in 1996, but those four years disproportionately swayed my sartorial leaning, and that never feels truer than in the fall. Keep scrolling to see which 90s icons are inspiring me at the moment, along with what stuff I’m eyeing in an attempt to approximate their looks.
1. The One and Only CBK
I’ve decided that this outfit is my future blueprint for showing off every cool pair of sneakers that I own. The oversized black fleece + roomy white pants combo is equal parts effortlessly cool and perfectly neutral, thus allowing kicks to do both the walking and the talking.
I think it’s about time for me to invest in a good suit, and since “true adult me” is a ways away from manifesting, practicality isn’t my main concern. I would love to get my hands on a mint green number like this one worn by Salt-N-Pepa and Spinderella, but I think this bubblegum pink situation or melodramatic purple option will do the trick. And although PVC has certainly been having a moment, I would personally update this look with a python printed baguette.
This image of Gwyneth Paltrow must be tacked up on a mood board somewhere, because how else would Zara’s perfectly 90s, equally Kelly green knit set come to exist at this very moment? I’ve decided it must be fate, and I’d like to embrace it completely with this sizable Telfar tote clutched in my palm and my toes planted into this pair of kitten toe mules.
Since Amelia put so many damn-good khakis on my radar, I’ve been racking my brain on how I can get some skin in the game. As she mentioned, it’s easy for khakis to read preppy or skater-y, but this photo of Aaliyah has inspired me to make these two lanes merge into one. I’d love to wear a jumbo sweatshirt and billowy khakis like hers, but rather than finishing the look off predictably with sneakers, I’m envisioning a pair of black and white Weejuns.
5. Princess Di
Seeing this photo of Princess Diana instantly made me realize that cropped pants are a luxury that I won’t have for much longer; exposed ankles and wind chill are like the sun and the moon in that they simply aren’t to be experienced at the same time. To celebrate the fleeting moments of the weather being on my side, I’m shopping for cigarette pants and sling backs as we speak.
Now it’s your turn. I’ll be waiting in the comments to hear all about your personal 90s style dreamboats.
Feature photo by The LIFE Picture Collection via Getty Images.