How One Millennial Learned to Stop Worrying and Love the Denim Maxi Skirt

They say what goes around comes around. And nowhere does that maxim ring truer than in the world of fashion where designers relentlessly loop back to styles from decades past for inspiration, breathing new life into old trends to create a kind of bricolage between past and present that results in something totally novel.

All things that were cool, given just a decade or two, are destined to be cool once again. And due to this industry-wide obsession with reviving the clothes of yesteryear, it appears the time has finally come for millennials to face the music…and that music is set to an *NSYNC soundtrack.

Gen Z has officially rediscovered the aughts in all its glory and are mining that time period’s aesthetic for everything it’s worth. A fact which, as someone who came of age during that era, chills me to my very core.

Low-rise pants, platform flip-flops, handkerchief hemlines — even flip phones and Christina Aguilera-inspired vajazzling have all come back into the zeitgeist and nothing has ever made me feel older.

But it’s not just those born after 1995 who have incorporated these styles into their closet. My fellow millennials and even Gen X-ers have suddenly started wearing apparel I associate exclusively with pre-pubescent angst.

So in an effort not to become some old fuddy-duddy who starts lecturing the youth about fashion “back in my day,” I decided it was time to unpack my sartorial-based adolescent trauma and join the masses in taking these aughts trends for one more spin around the block. [Editors’ note: Back in my day, we learned the hard way that platform flip-flops are the fastest way to sprain an ankle. But we digress.]

The Denim Maxi Skirt

I first noticed denim maxi skirts cropping up over the summer on stars including Emily Ratjajkowski, Gigi Hadid and Nicky Hilton. But these skirts were not the tubes of heavily whiskered and faux mud-splashed denim I remembered from my youth. The 2023 iterations of the style feature updated details like ruffled hems, subtle cutouts, and — dare I say — sexy thigh-high slits, all of which make the look feel much more “considered” and less like you’re just trying to obscure as much of your lower body as possible.

I knew from the jump that this was going to be a tough trend for me to get on board with considering my strongest association with denim maxi skirts are the religious cults I used to see wearing them while visiting my grandma in rural Missouri. So I didn’t have particularly high hopes when I first stepped into Alice + Olivia’s “Rye” denim maxi.

However, the first thing I noticed about this modern take on the aughts style was the stretch. The generous give of the fabric combined with its high-rise waistband acted almost like a pair of built-in Spanx, sucking in and cradling my little stomach paunch to create one long, smooth, uninterrupted jean-clad curve.

And while I was initially trepidatious about the skirt’s opening in the front and just how much of my inner thighs it leaves exposed to the elements, I have to admit, this too ended up being oddly flattering. The slit acts almost as a frame for the legs, making them look longer and leaner than the gams I’ve been genetically blessed with.

While I do still feel a bit like a country mouse in the big city walking around my hip-to-death Brooklyn neighborhood, in a skirt that wouldn’t look so out of place next to a hay bale, all it took was one subtle nod of approval from a Gen Z fashionista walking towards me on the sidewalk for this garment to seriously grown on me. 

The Mary Jane

Back at the turn of the millennium, I was staunchly a Nike trainers and Doc Martens type of girl, so I don’t have any particularly negative connotations associated with Mary Janes dating from that era of my life. That said, when I first slipped on Sam Edelman’s “Michaela” Mary Jane flats, a near identical dupe of the thousand-dollar version made by The Row, they immediately conjured images of my childhood American Girl doll Samantha, her flat-footed double-wide tootsies, and the little plastic dress shoes she came with.

While Mary Janes have quickly become the beloved shoe of perennially cool street style stars like Kaia Gerber, Zoë Kravitz, and Margaret Qualley, “cool” was not exactly how I felt upon my first foray out in them. To me, the footwear made me look like some weird adult baby or one of those middle-aged women who are deep into Lolita cosplay.

But over the course of the week, as I tried styling them with various pants and dresses in my closet, my distaste at how infantilized and aggressively feminine these shoes felt quickly began to wane. It certainly helped that they’re incredibly comfortable, and at a statuesque 6-ft.-2-in. I struggle to find shoes that look dressy but don’t add even more inches to my already giantess-adjacent build.

I also realized that Mary Janes possess the remarkable ability to instantly pull together a look, whether that be a black-tie evening gown or a pair of Alo leggings. And anything with the power to make me look effortlessly chic when I’m at my most discheveled and lazy instantly achieves icon status in my book.

The Torso-Sized Handag

A purse the size of my enitre body might be the one resurrected trend from my youth that I was actually patiently awaiting the return of.

After years of carrying purses so tiny my iPhone peeks out of the top of them, I was more than ready to return to everyday satchels that can easily double as a weekender bag in a pinch. So when I saw people like Katie Holmes, Hailey Bieber, and Mary-Kate Olsen (a woman who both originated this trend and has never truly given up on it) suddenly opting for bigger and bigger bags, I feverishly raced to my closet to dig through my archive of aughts treasures I can’t seem to part with and unearth my own giant leather purse from circa 2010 that extends from my armpit all the way down to my hipbone.

And just as I thought, it was once again love at first carry. Especially living car-free in N.Y.C., it’s a luxury to feel like your own one-woman SUV, filling a bag with not just the essentials, but books, sweatshirts, a change of shoes, and any other random bits and bobs that might come in handy while out and about.

But after a week of blissful reunion, it became apparent why we all retired this style in the first place. While my purse psychically transported me back to the days of being 17 again, unfortunately my 30-something body did not time-travel with it. Throwing out my back or tweaking a muscle is already easy enough without actively trying to give myself scoliosis in the name of fashion. So while I’m happy to be reunited with my first real handbag, I’m sorry to report than an XXL tote, no matter how fabulous or ludicrously capacious, might still be more of a young person’s game.

So what did this fashion experiment teach me? First of all, that clothing — even the clothing I associate most strongly with 7th grade bullies — can’t hurt me.

And secondly, that sometimes a trip down trend memory lane can give you a whole new perspective, not only on the clothing or accessory in question, but also the ideas you’ve attached to it.

By instinctively dismissing these trends that haunted me in my youth, I was also shutting down the opportunity to interrogate my own beliefs about both the origins of my sense of style and my sense of self.

My week of aughts fashion immersion provided me with a new lens through which to think about who I am and what I wear, an exploration that probably saved me at least three years worth of therapy. Just call me Dr. Emily Kirkpatrick, Fashion PhD.

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