What ’90s-Era Tommy Hilfiger Taught Me About Personal Style

holding mytheresa tommy What 90s Era Tommy Hilfiger Taught Me About Personal Style

Of course ’90s-era Tommy is back. (Photo: MyTheresa)

It’s 1993, Manhattan, and day one of my new middle school. As a tween prone to fairly preppy, opinion-free clothing, I wore tapered light jeans, a navy tucked-in Sam and Libby tee with a giant gold sun on the front, brown suede oxfords, and carried a ridiculously large leather briefcase-satchel hybrid. I remember thinking my outfit was—to use ’90s parlance—the bomb diggity.

Until I rolled up to homeroom and saw what appeared to be every other kid decked out in giant pieces emblazoned with a mysterious red, white, and blue rectangle. That symbol was, of course, indicative of Tommy Hilfiger, a relatively unknown designer who was gaining steam with the streetwear crowd—also known as every kid from the age of 12 to 20 in New York City during the Dinkins days.

I remember having a very new, very visceral reaction to the unambiguous logo, the oversize cuts, and the status-y accessories, so—because my mom wasn’t forking over upwards of $50 for clothes she thought I wanted to fit in—I saved every cent of my birthday money to buy a few specific items: a thick cotton Tommy tee that hung past my knees, a white canvas overnight bag, and a pair of banded briefs I picked up in the men’s underwear department at Macy’s on 34th Street, which I let peek out beneath my (new, baggy) jeans. Let the record show muddy brown lipstick (Revlon’s Toast of New York was my school’s shade of choice), giant gold door-knocker earrings, and Nike Huaraches were also worn at this time.

Yep, I still have my '90s-era Tommy briefs (Perrie Samotin)

Yep, these are mine from the ’90s—and I still have them. (Perrie Samotin)

Not only did I genuinely love these items, I also loved the little cardboard tag they came with at the time; it featured the label’s icon, and everyone at school let one hang from the zipper of their Jansport backpacks—logomania at its absolute peak, and I bought right in.

As with most material things, I ended up cycling through them and moving on to new labels (Timberland, Fila, JNCO, a brief and unfortunate flirtation with Karl Kani), and I got rid of my tee and—regrettably—the amazing bag. I do still have the briefs, though, which I keep in a drawer because, well, nostalgia.

And though I moved away from exclusively wearing clothes 10 sizes too big as the decade approached its end and started to gravitate toward other looks that defined the era—stretchy spaghetti strap tops à la Amanda Beckett in Can’t Hardly Wait, goth-y Steve Madden flatforms, mini backpacks, straight strapless sheaths), I’m still in awe of my wholehearted dedication to embracing a specific look—I wore those Tommy pieces for a solid four years.

bag What 90s Era Tommy Hilfiger Taught Me About Personal Style

The amazing duffel that I gave away. (Photo: ’90s Throwback Streetwear)

Was I obsessed with Hilfiger and streetwear because everyone else was? Maybe in the beginning, but I remember for the first time in my life really feeling like I had a style I identified with—that I knew exactly how I wanted to look and what pieces could get me there. That was a valuable lesson for a kid who, before, mostly just wore what her mom picked out. Plus, there was no online shopping in the ’90s, so I still—to this day—remember the pure thrill of finding items I’d hoped were in stock hanging in a store.

Two decades later, the ’90s have officially permeated every aspect of today’s culture, from television to fashion and beauty, so I can’t say I’m surprised that Hilfiger is revamping the decade’s most iconic pieces for a capsule collection to be sold at Mytheresa.com.

Modeled by sisters Suki and Immy Waterhouse (who were actual babies when I first walked into my new school, FYI), the line offers eight pieces priced from $198 to $654.

Expensive to be sure, especially when the real stuff can be found on Etsy, eBay, and in every Goodwill from New York to California, but I get that these aren’t reissues of classic pieces—they’re elevated, modernized takes that the fashion crowd would be proud to wear without a hint of irony. (Okay, maybe a hint.)

Aaliyah '90s Hilfiger ad.

Aaliyah’s famed ’90s Hilfiger ad.

Expect updated versions the label’s beloved cropped flag sweatshirt (now rendered in velvet), as well as silk boxers, varsity jackets emblazoned with H, tees, and—my personal favorite—the flag bandeau top, made famous by ’90s icons like #queen Aaliyah.

I never had the nerve to wear that one when it was originally released, I but might give it a go this time around. Might even break out the briefs, too.