Alright, so I’ve been on a bit of a kick lately, diving back into Aaliyah’s fashion. It’s funny how styles come back around, but her look always felt timeless to me, you know? Effortlessly cool. So, I figured, why not try and capture some of that vibe myself? This is kinda how I went about it.

Getting Started: The Observation Phase
First thing I did, I just immersed myself. I spent a good few evenings pulling up old music videos – “Are You That Somebody?,” “Try Again,” “One in a Million” – all the classics. Then I went down the rabbit hole of photoshoots and candid pics. I wasn’t just looking at the clothes, but how she wore them. There’s a certain attitude, a relaxed confidence that’s key.
I started noticing the recurring themes. Baggy pants were a huge one, often paired with a smaller top, like a bandeau or a crop top. She rocked a lot of sporty stuff, athletic wear, but made it look high fashion. And let’s not forget the dark sunglasses, even indoors sometimes. Iconic.
The Hunt for Pieces: Trial and Error
Okay, so observation is one thing, actually finding the stuff is another. My first mission was the baggy pants. I thought, “Easy, right?” Wrong. Finding that specific 90s/early 00s silhouette without it looking like I just grabbed my dad’s old jeans was a challenge. I hit a few thrift stores first.
- I rummaged through endless racks of denim. Found some potentials, but the fit around the waist was often weird if the legs were baggy enough.
- Then I looked online, trying to find modern equivalents. Some brands are doing the looser fit now, but it’s still not quite the same drape as those older pieces.
Next up, crop tops. Again, not as straightforward as you’d think. A lot of today’s crop tops are super flimsy or overly cutesy. Aaliyah’s often had a sportier edge, or were more structured, like a bandeau. I managed to find a couple of simple, thicker strap bandeaus that felt right. I also experimented with just tying up an oversized t-shirt, which actually worked pretty well for a casual look.
I also kept an eye out for oversized jackets and men’s shirts. She often played with masculine and feminine elements. I found a decent oversized bomber jacket that I think has potential. The key, I learned, was the contrast – big on the bottom, small on top, or an oversized jacket over something fitted.

Putting It Together and The “Vibe”
So, I had a few pieces. Now it was about making outfits. This was the fun part, but also where you realize it’s more than just the clothes. It’s the swagger. I’d put on some baggy jeans and a small top, but something still felt… off. Then I’d add some simple silver hoops or a dark pair of sunglasses, and it started to click a bit more.
I realized comfort was a massive part of her style. Even when it was sexy, it never looked restrictive or like she was trying too hard. It was all about that effortless cool. So, if something felt fussy or uncomfortable, I knew it wasn’t quite right. It had to feel natural.
I also played around with layering. An open, oversized shirt over a bandeau with those loose pants – that started to feel very Aaliyah. It’s a balance. You don’t want to look like you’re wearing a costume, but more like you’re taking inspiration.
Where I’m At Now
So, have I completely transformed into Aaliyah? Definitely not, haha. But I’ve definitely incorporated some of those elements into how I dress now. I’m much more open to playing with looser silhouettes on the bottom, and I’ve rediscovered my love for a good simple crop top or bandeau when the weather’s right.
It’s been a fun little style experiment. It’s not about perfectly copying her outfits, but more about capturing that feeling – that blend of tomboyish comfort, understated sexiness, and undeniable confidence. I’m still tweaking, still playing around, but it’s definitely made getting dressed a bit more interesting. And honestly, who doesn’t want to channel a little bit of that Aaliyah cool?
