After five years of working in fashion, I've pretty much seen it all when it comes to trends, so much so that very rarely am I surprised by the otherwise puzzling fads that come and go on a weekly basis. Belly chains, whale tails, and $200 pre-ripped tights don't phase me, nor do pant-heels and those Y2K-era platform flip-flops. Even so, the latest trend to go viral on Instagram has me admittedly stumped. Once you see it, I can almost guarantee that you will be too.

Stemming from what TikTok is calling "Adam Sandler Summer" is a puzzling trend that despite being the antithesis of chic, is quickly becoming one of the most talked about of the season: basketball shorts. Indeed, some of social media's most trusted style sources are wearing the knee-length, mesh, or shiny polyester shorts that every 12-year-old boy dons on repeat. And get this: They're doing so unironically, all in the name of dressing like Adam Sandler. 

On Isabella Lalonde: Nike Classic Cortez Sneaker ($80)

On Laura Reilly: Esse Studios Strapless Camisole ($215); Nike shorts; Balenciaga Cagole Sandals ($995)

Naturally, after noticing how cool people were making this very much uncool wardrobe item appear, I decided to test the trend out for myself. Three thrift stores, an Urban Outfitters, and a sports-specialty shop later, I was well on my way to making basketball shorts look, well, good. Scroll down to follow along in my journey through the only trend to throw me for a loop in half a decade. And while you're at it, go ahead and shop the shorts style that's blowing up on Instagram and TikTok. 

As luck would have it, the first store I went to had a pair of basketball shorts that were obviously cool and surprisingly approachable in that they are slightly shorter than the knee-length pairs frequented by Sandler and have a more tailored fit. By Mitchell & Ness, the style features the colors and logo of the New York Knicks, so as an adopted New Yorker (sorry to my hometown team, the Chicago Bulls), they were practically perfect. Keeping the look simple but elevated, I added a structured, ribbed tank by Caes and my favorite black loafers from Loewe.

Oh, and did I mention that I got at least a dozen questions about these shorts during my walk in them from SoHo to the Lower East Side? If that's not a sign to get yourself a pair, I don't know what is. 

Admittedly, this pair of shorts—a men's Nike pair that I scored from Union Square's resident sports supply store Paragon—was more difficult to style in a way that didn't feel gimmicky. But on a day as hot as this one was (the real feel was 99ºF in NYC) was beyond grateful to have an excuse to wear breezy gym shorts and a bra top. After I decided on that warm-weather combo, I wanted to stylize the look a bit, so I threw on everyone's favorite summertime essentials: an oversize white button-down shirt and a matching pair of Maryam Nassir Zadeh wedges. Once I had, I felt completely at ease spending a day in this look. In fact, I'm already planning on wearing it again. 

This one goes out to all my L.A. fashion girls.

Loving the retro '70s vibe of these.

The perfect mix of fashion and function.

If you don't want to wear a full-fledged team logo, just pick a pair in your team's color palette. 

Dua Lipa is on board with the trend, so you should be too. 

True basketball-shorts fans will know that Eric Emanuel's styles are the coolest by far. 

Clearly, you need a pair of Jordans. 

You can't go wrong with Nike's selection. 

Whatever team you root for, I bet you can find a cool pair just like this one that supports them. 

Simple, black bball shorts are the perfect place to start. 

In case you wanted a funkier version of my Knicks shorts. 

Now that I've mastered simpler styles, I'm ready to tackle these bright-yellow shorts next. 

Baby pink is seriously trending at the moment. 

My personal favorite fall color combo. 

A subtle pattern never hurt anybody. 

Okay, Isabel Marant—go off. 

Next: I Spend Hours on Insta Every Day—9 Trends Literally Everyone's Wearing RN