'90s-Era Tommy Hilfiger Outfits We Still Want (and Ones We Don't) | YUYU YUYU

'90s-Era Tommy Hilfiger Outfits We Still Want (and Ones We Don't)

Audrey O'Brien February 13, 2016 February 23rd, 2017

If you for some reason have been living underground for the past year and half (which, I mean, why not stay there until the election is over, at least), we’re here to tell you that 90s fashion is back. If you don’t believe me, then the fact that Gigi Hadid just had a collection show with Tommy Hilfiger during New York Fashion Week should clue you in.

Honestly, I’m a big fan of the 90s aesthetic so I’m not at all opposed to this comeback. But, as with all good things, this retro revitalization should be embraced in moderation. Here’s a rundown of Tommy Hilfger #looks from the 90s I hope I can run into in a thrift store, and ones that make me glad my mom was still dressing me back then.


Well it doesn’t really get more 90s than Kate Moss. This outfit really fits the ‘athleisure’ trend in today’s fashion aka the trifecta of looking good, feeling comfy, and pretending you’re actually going to go the gym today. It combines the classic high waisted bottom with a crop top, a brightly colored windbreaker, heretofore mythical shorts that are actually comfy, and the best kind of shoes: sneakers (don’t argue with me on this unless you’ve worked in retail and had to stand for 8 hours in sandals that you previously THOUGHT were comfortable but now the joke’s on you and you sincerely do feel hell beneath your tired and swollen feet. This is highly hypothetical, obviously).

What else would I wear to my end of summer boat party? Really, I think you need a hint of irony and a bit of Rihanna-esque confidence to pull this outfit off in 2016, but in my opinion it’s totally doable.

The Sweater. Preppy sweaters have never really left the mass population (or maybe they have, but I’m from New England so I didn’t notice), but this one looks especially cozy. Honestly, most 90s Tommy Hilfiger sweaters I would deem appropriate for this list: they encompass that blatant 90s aesthetic without going so over the top.

So this duffel isn’t technically an outfit, like, in any way at all but I feel like I need it to be complete as a person, so it’s going on the list. I mean, yeah, it totally encompasses the Brand over everything mentality of the 90s and early ’00s (and among especially tacky people today), but at the end of the day we’re all beholden to capitalism anyway so I WANT IT.


Ok, Mama Tina Knowles was known to take the matching outfits a bit too far sometimes, and this is no exception. I don’t really know what they were going for, but there are definitely many better ways to show off Kelly’s abs. Just like LaTavia and LeToya, this look needs to be left behind for the new generation.

I would apologize for the quality of the above pictures, but to be honest, you don’t want to see it in hi-res. I don’t know what’s happening with this outfit, and I don’t really want to know. I’ve tentatively thinking of experimentally wearing my bodysuit under some leggings (it’s embarrassing that I just admitted that) but this just convinced me not to. If normal basketball shorts are ill-fitted, I don’t know what category of ‘fit’ these ones fit into to. There’s not even anything to salvage here to wear ironically. Tragic.

I love overalls. LOVE. They’re basically the only way you get force me out of my leggings and into denim. I even like them baggy (they provide a perfect way to comfortably leave space for a food baby while also hiding said food baby). But these look like something a mother forces her 5 year old into. Don’t worry she also bought them a little big so her daughter has room to grow!  It’s overalls and it’s peak Britney: I want to love it, but I just can’t. Although sadly, this is probably one of Britney’s better fashion moments.

Ok. I KNOW this is controversial. Aalyiah was the face of the brand, and what most people think of when they think 90s Hilfiger they think of her rocking the tube top. I’m not here to argue that she doesn’t look great. She totally pulls it off. But, let’s be real, no one else could or ever will. It’s just, living in New York City, I feel like walking past someone in the street attempting to wear those pants is at a very high probability. I don’t want that. Ever. Let’s all agree to just retire them now. Or 20 years ago.