I had a realization this week, and I am very predictable. It turns out, my music and my footwear go hand-in-hand… or foot-in-foot?

This year has ushered in a few “I’m getting old” moments for me, not the least of which is the fashion cycle, recycled back to exactly what I wore in high school. It’s the socks with sandals, the leisure wear and open flannels (that yes, now I see, Mom—it does look like you just rolled out of bed); and it’s how the legs of jeans are once again getting wider and wider. (I heard an internet rumor that skinny jeans are the new mom jeans and Gen Z is on a mission to cancel them entirely. How very angsty and grunge.)

A few years ago, I joined the Serenity team, starting with my other column, “Steep Thoughts,” and an article about my shoes—my pointy-toed, metallic silver mules that one mom at school drop-off affectionately called my elf shoes. Still undergoing my transformation from city girl to mountain woman, I turned to the tangible forms of expression I’ve always been able to rely on: fashion and music. And I found in those modes of expression opportunities for both nostalgia and reinvention. If I was to live in the mountains, I needed some sturdy, weatherproof boots, and I wasn’t going to give up the elf shoes—wasn’t going to give up on that old part of myself.

Overly philosophical or not, what else can stir this sensation for us more than music? Hear that old high school tune and you’re transported, not only to another time, but almost into another self. This resurgence of ’90s culture has me oscillating between my grown-up self and what it felt like to be a late-’90s teen. It’s partly the angst, but it’s mostly remembering the feelings of possibility, of individuality and of self-identity. I think those are important things for anyone to revisit at any age.

My closet floor looks much like it did in high school (except I can afford to buy the real brands now, not the knock-offs), and my playlists are a mash-up of old and new. Take a look at the shoes on my feet and you can also bet on what I’m pumping through my headphones. Some days, I’m relying on those artists who inspired who I was then and some days, I’m playing artists of today who can give the same feels to the person I am now.

Doc Martens. In that space between ’80s punk and full-on grunge, we youth adopted military-inspired footwear. I suppose it was a desire to be indestructible, ready for anything, and for me, at least—taller. In that same mindset, the go-to soundtrack was Joan Jett, who assured me that it was good to be angry and it was good to be a girl. Nowadays, in a Doc Marten mood, I like to sing along with Sharon Van Etten, whose voice has the same raspy, tough-girl quality, but like grown-up me, she studies her youth from a retrospective place.

White sneakers. I don’t know—the teens of the day have adopted a sneaker that looks like a cross between a hospital shoe and something from the wardrobe closet on-set at Seinfeld. In my day, and here I’m going to stick with what I know, the white sneaker of choice was an Adidas, always a little bit dirty. You should slip them on and off without untying them. They were expected and accepted all the same. You couldn’t be a kid in the ’90s and not have white sneakers; you couldn’t be a kid in the ’90s and not like Nirvana. In 2021, I get that same comfortable feeling from Vampire Weekend. Sure, they’ve been around for a while, but their new music is as easy to slip on as your broken-in Adidas.

Black high tops. Fill me in, youths. Are you still doing the Vans thing? (You didn’t invent that.) Much like the white sneaker, this weekend go-to offered comfort with a kick-ass appeal. As a mature adult, I’ve upgraded my high tops, having scored at the EChO thrift shop a few months back with a pair of unworn YSL double laced leather high tops. They’re bad-ass but a little bit fancy. Kind of like Regina Spector will always be—kind of like Billie Eilish is now.

Birkenstocks. The kids were so smart to revive some trends. Who doesn’t love a shoe you can slide on and still feel like you’re barefoot? It’s amazing to see that, as in the ’90s, the Birkenstock is not reserved for the summer, and I have been known in 2021 to show up to yoga class in my Birks and fuzzy socks. The summers of my youth are hazy and warm like a Dave Matthews Band concert, music that makes you sway and everyone around you knows every word. I don’t go to many big concerts anymore, but Mac DeMarco evokes the same sway when I’m making dinner and packing school lunches. (And my Birks make great house shoes.)

Chelsea boot. My most reliable and shearling-lined mountain shoe is modeled after the boot that made us dream of our grown-up urban adventures. Somehow, a Chelsea boot, cliche as it is, makes you instantly intellectual and cultured. Sufjan Stevens can be listened to at any time of life and he never ceases to be brilliant, but if you want a modern take on this ethereal headspace, I love the new Fleet Foxes album.

Shoes on, music turned up, you’re ready for a walk no matter what your mood.