Tomboy Outfits: How Celebrities Rock the Look

Baggy jeans. A boxy blazer. Sneakers you could actually walk in.

Tomboy style has been around forever, but lately it feels like every celebrity off-duty photo is basically a masterclass in it. And honestly? It's one of the comfiest trends to copy.

What Is Tomboy Style?

At its simplest, tomboy style means borrowing from the boys. Think oversized tees, loose trousers, button-downs, hoodies and flat shoes instead of heels.

But it's not about looking sloppy. The best tomboy outfits mix those relaxed pieces with one or two girly touches, like a pair of gold hoops, a slick bun or a fitted crop top.

It also changes a lot by decade. In the 90s it was all about hip-hop and skate culture. Now it's more polished, with oversized tailoring and quiet basics leading the way.

The OG Tomboy Icons

Aaliyah

If there's one name that comes up every single time tomboy style gets mentioned, it's Aaliyah.

Baggy jeans slung low, a tiny crop top, a bandana, dark sunglasses and that famous side-swept hair falling over one eye. She made it look cool and sexy at the same time, which isn't easy.

In the mid-90s she fronted ads for Tommy Hilfiger, and the look still pops up on mood boards today. It's one of the defining moments of 90s fashion, full stop.

Gwen Stefani

Back in her No Doubt days, Gwen Stefani was all tank tops, track pants, Dickies and sports bras, finished off with bright red lipstick.

That contrast was the whole point. Tough skater-girl clothes, glam old Hollywood makeup. Nobody else was doing it quite like her.

Avril Lavigne

Then came 2002, and Avril Lavigne showed up in a tank top, a loose necktie, cargo pants and chunky sneakers.

Teenagers everywhere immediately raided their dad's tie drawer. Songs like Complicated and Sk8er Boi made her the face of the skater-tomboy look for a whole generation.

Celebrities Who Nail Tomboy Style Now

Hailey Bieber

Hailey Bieber has pretty much perfected the off-duty tomboy uniform. Oversized blazer, baggy jeans, white socks with loafers, a baseball cap and gold jewelry.

It looks like she grabbed whatever was closest. It also looks like it cost a fortune. That's the trick she's so good at, and her street style gets copied all over TikTok.

Zoe Kravitz

Zoe Kravitz keeps it minimal and a little moody. Slouchy suits, men's-style trousers, plain white tanks and black boots are her go-to.

She rarely looks like she's trying hard, and somehow that's exactly why it works. Tailoring, minus the stiffness.

Rihanna

Rihanna can wear literally anything, but some of her most iconic street style moments are pure tomboy. Huge sports jerseys worn as dresses, baggy jeans, oversized hoodies and chunky sneakers.

She usually adds one dramatic touch, like a bold lip, a stack of chains or a tiny designer bag, so it never looks plain.

Zendaya

Zendaya's red carpet looks get most of the attention, but she's also a big fan of menswear. She's shown up to more than one press event in a sharp, oversized suit instead of a gown.

With stylist Law Roach, she proved suits can be just as glam as any dress.

How to Get the Tomboy Look

Good news: you probably don't need to buy much. A lot of tomboy style comes down to how you wear things, and most of it is probably in your closet already.

These are the pieces worth having:

• Baggy or straight-leg jeans. The looser the better.
• An oversized blazer, ideally one that looks borrowed.
• Plain white tees and tank tops, lots of them.
• A crisp button-down shirt you can wear open or half-tucked.
• Hoodies and crewneck sweatshirts.
• Cargo pants or relaxed trousers.
• Clean sneakers, loafers or chunky boots. No heels needed.
• A baseball cap or beanie.

Then add something a little feminine so it doesn't look like you're wearing your brother's laundry. Gold hoops, a slick bun, a swipe of lip gloss or a fitted crop top all work.

Easy Tomboy Outfit Ideas

1. Oversized blazer, white tee, baggy jeans and loafers. The Hailey Bieber special.
2. Crop top, low-rise baggy jeans and a bandana, very Aaliyah.
3. Tank top, loose tie, cargo pants and sneakers, if you're feeling 2002.
4. White tank, slouchy black trousers and boots, Zoe Kravitz style.
5. An oversized jersey or hoodie with bike shorts and chunky trainers.

The golden rule? Keep at least one thing roomy. That relaxed, slightly borrowed fit is what makes it tomboy.

Final Thoughts

From Aaliyah's low-slung jeans to Hailey Bieber's giant blazers, tomboy style has never really gone away. It just keeps getting reworked for each new generation.

And the best part? It's comfortable. Not many trends can say that.

If you like your style with a bit more edge, our guide to the grunge aesthetic is full of flannels, combat boots and Kate Moss-approved slip dresses.