Okay, so I decided to dive into Aaliyah’s iconic outfits today. It kinda started randomly, I was listening to “Try Again” and remembered how cool she looked in that video. That got me thinking about her whole style vibe, which was just… something else. So, I figured, let’s make a little project out of it, try and catalogue what made her look so unique.

First off, I just opened up my browser and started searching, pretty basic stuff like “Aaliyah style” and “Aaliyah best outfits”. Lots of pictures popped up immediately, which was great. It kinda confirmed what I already remembered – lots of baggy pants, crop tops, sporty vibes. Very 90s/early 00s, but still looks fresh now.
Then I tried to get more specific. I started thinking about particular music videos or appearances. That Tommy Hilfiger outfit, you know the one? Blue, white, red bandeau top and those super baggy jeans. That was definitely top of the list. I hunted down a few good pictures of that one specifically. It’s probably the most recognized look, right?
Breaking Down the Vibe
I started noticing patterns. It wasn’t just one thing. So I started making a mental list, then actually jotted some stuff down:
- Baggy Bottoms: Jeans mostly, sometimes track pants. Always loose-fitting.
- Crop Tops/Bandeaus: Showing off the midriff was key. Often sporty or simple.
- Oversized Jackets/Shirts: Sometimes layered over the crop tops.
- Menswear Influence: Definitely borrowed from the boys, but made it feminine.
- Dark Colors/All Black: Remember the “Try Again” video? That sleek black leather look. Found some great shots of that too. Very smooth.
- Accessories: Sunglasses were a big one, often dark and sleek. And bandanas sometimes.
I spent a good while just scrolling through image results, saving the ones that really stood out. Like, the outfit from the “Are You That Somebody?” video, kind of earthy tones, still baggy but different. And her looks from award shows or events, sometimes more glam but still with her signature edge.
It’s interesting how she mixed sporty, street, and sometimes a touch of goth/futuristic vibes, especially with the all-black outfits. It wasn’t just slapping clothes together; you could tell it was thought out, it was her.

Putting It Together (My Notes)
So, I ended up with a folder full of pictures and some rough notes. I didn’t go super deep into like, exact brands for everything (except the obvious Tommy stuff), but focused more on the elements of the outfits. The shapes, the combinations, the attitude.
What I realized doing this little exercise is how much her style was about confidence. She wore those baggy clothes and crop tops with such ease. It wasn’t just the clothes; it was how she carried herself in them. That’s probably why it still resonates, you know? It felt authentic.
Yeah, that was a fun little dive. Didn’t uncover any massive secrets, just spent some time appreciating a truly unique style icon by looking back through her most memorable looks. It’s cool how someone’s way of dressing can still feel so relevant years later.