Let’s be real: for the past five years, the only people wearing skorts were your cousin’s Goldendoodle’s trainer and that one influencer who’d never touched a racket in her life. The garment felt like a weird compromise between pants and a dress, like a mullet for your legs. But we’re living in the era of unexpected remixes, and Neo-Prep 2.0 has flipped the skort into the single most versatile piece in my late-winter rotation. It’s giving tennis club nostalgia, but crossed with a thrifted boxy blazer and a pair of silver hoop earrings that cost more than the rest of the fit combined. And honestly? That’s the entire point.

The thing about Neo-Prep 2.0 is that it doesn’t take itself seriously. It’s a micro-trend that borrows the buttoned-up bones of classical preppy—think boat shoes, cable knits, equestrian leathers—and then cracks them open to stuff them with the messy, bohemian energy of somebody who owns a $15 vintage leather jacket and a serious squint. The skort fits into this because it’s inherently contradictory. It looks like a skirt until you start moving, then suddenly it’s shorts and you can chase the last train without flashing half of Ditmas Park. That duality? That’s the Brooklyn vibe. It’s polished from the front, but functional from the inside. Just like the rest of us.

But let’s talk styling, because that’s where Neo-Prep 2.0 actually lives. You can’t just throw on a pleated skort from a fast-fashion drop and call it a day. That’s giving “2016 Pinterest board.“ Instead, you need to treat the skort like a blank canvas. Start with a slightly oversized Oxford shirt, untucked and loose, and add a cable-knit vest over it. The vest should be those weird, cropped ones that end right at your ribcage—the more grandma-ish, the better. Then, swap the typical loafers for a pair of chunky platform sneakers that’ve been through a couple of basement shows. Add a slouchy backpack that’s more bohemian than preppy, and finish with a metric ton of rings. The vibe is not “I just came from a country club” but more “I raided my mother’s 1990s L.L.Bean catalog and then walked through five boroughs of secondhand smoke.“

The real secret to Neo-Prep 2.0’s skort is layering, because the world doesn’t care about your à la mode skirt when it’s 6 degrees outside. Throw on a pair of sheer black tights under the skort—yes, under—and then add some knit leg warmers that you bought on Etsy from a seller who clearly ships from a cottage. The juxtaposition is clean and chaotic, just like a thrifted Ralph Lauren blazer that’s three sizes too big but somehow makes you feel like the CEO of your own small online vintage business. And don’t even get me started on the carabiner keychain. That’s the ultimate Neo-Prep accessory. It says “I have a bike and I also have a 401(k) from my internship at a tech startup that lets me wear whatever I want.“

Budget-wise, this is the trend that literally begs for a thrift run. I’ve seen the same pleated skort from that viral TikTok shop sold for $60, but you can find a near-identical corduroy skort on the rack at your local Goodwill for $6. The trick is to look for something with a slightly A-line or pleated shape, then give it a good steam. The worst thing you can do is let it look brand new. The best thing you can do is let it look like it’s lived a little. That’s the Fast-Fashion x The RealReal mentality: buy the dupe to feel good, then score the one-of-a-kind vintage find on resale to feel real. Actually, the whole idea is to mix a high-quality piece (like a silk skort from a designer resale) with a crusty hoodie you stole from your favorite cousin. That’s the baller-on-a-budget energy.

So, whether you’re an actual tennis-loving trust-fund baby or just a person who watches a lot of Succession with a glass of boxed wine, the skort is your entry point into Neo-Prep 2.0. It’s the short-sleeved collared shirt of bottoms. It can be prim, it can be grunge, it can go full-boho and pair with a fringe leather bag and some turquoise earrings. Honestly, the skort is not just a cut of fabric; it’s a life philosophy. It’s saying that you don’t need to choose between looking cute and being functional. That’s the whole game. So go ahead, add a skort to your next rental box or thrift haul. Your future self—the one sprinting to a 9 AM lecture in a pair of slightly muddy sneakers—will thank you.