So, the other day, I was just scrolling, you know, doing nothing much, and bam! An old Aaliyah music video popped up. Man, it hit me. Her style back then? It was something else. Completely effortless, cool, kinda tomboyish but still really feminine. Made me think, could I actually pull off something similar today? Not like a costume, but inspired by it. Decided right then, gotta give it a shot.
Getting Started
First thing, I needed a plan. Couldn’t just grab any baggy jeans. Aaliyah had specific looks. I remembered the Tommy Hilfiger stuff, the crop tops, the low-slung pants, the bandanas. Yeah, that whole vibe. So, I spent a good hour or two digging through old pictures online. Saved a bunch on my phone. Looked kinda crazy, like I was stalking 90s fashion. But hey, research, right?
I decided to focus on a couple of key elements:
- The Bottoms: Definitely needed some baggy pants. Jeans or maybe cargo pants. Low rise was key.
- The Top: A crop top or a sports bra type thing. Maybe layered under an open jacket.
- The Extras: Sunglasses were a must. Maybe a bandana or a beanie.
Didn’t want to copy an exact outfit, more like capture the feeling. You know, relaxed but put-together.
The Hunt for Clothes
Okay, this part was tougher than I thought. Finding clothes like that now? It’s weird. Fashion’s kinda circled back, but it’s not quite the same. Those super baggy, low-rise jeans from the late 90s/early 00s? Hard to find the right fit and wash.
I hit up a few thrift stores first. Figured that’s where the real gems would be. Found some decent baggy jeans, but most were either too trashed or just didn’t hang right. You know how specific that silhouette was? It’s all about the drape. Found a potential pair of cargo pants, though. Not perfect, but maybe workable.
Then I looked online. Loads of “Aaliyah inspired” stuff, but a lot of it felt cheap or just… wrong. Too modern, trying too hard. Crop tops were easy enough, thankfully. Got a simple black one and a white one. Also found a decent oversized denim jacket online, kinda like one she wore.
The struggle was real finding pants that sat low enough without looking ridiculous or feeling like they’d fall off. Seriously spent ages just trying to find the right bottoms. It’s funny how you remember a style, but recreating it decades later involves way more effort than just throwing clothes on.
Putting It All Together
Alright, got the pieces. Time to actually try and make an outfit. Laid everything out on my bed. Looked promising.
First attempt: Baggy jeans (the thrifted ones, slightly altered), the black crop top, and the oversized denim jacket open. Put on some chunky boots I had. Looked in the mirror. Hmm. It was… okay. Felt a bit bulky. Maybe the jeans weren’t quite right.
Second attempt: Switched to the cargo pants I found. These sat lower, felt a bit more authentic. Kept the crop top, ditched the jacket. Added some dark sunglasses I had lying around. Okay, this felt better. More effortless. Still wasn’t 100% Aaliyah, obviously, but it had that vibe. That relaxed, cool energy.

Tried adding a bandana, tied around my head. Felt a bit much for me, personally. Maybe needed the right attitude to pull that off, and I wasn’t feeling it. Sunglasses, yes. Bandana, maybe not today.
The Result and Thoughts
So, did I nail it? Nah, probably not perfectly. But I did manage to put together an outfit that definitely nodded to Aaliyah’s style, and honestly, it felt pretty cool to wear. Comfortable too, which is a big plus. The cargo pants and crop top combo worked best for me.
It really made me appreciate her style more. It wasn’t just about the clothes, it was how she wore them. That confidence. You can buy similar clothes, but you can’t buy the attitude. That’s the magic ingredient.
What I learned? Recreating iconic looks is harder than it seems. Finding the right pieces takes time, and even then, making it feel authentic and not like a costume is tricky. It’s also funny how styles come back, but always with a twist. Those exact cuts and vibes from 20 years ago? They’re ghosts in the fashion machine now. Still, it was a fun experiment. Made me dig out some old R&B tunes too. Good times.