Channel Your Inner Teenage Dirtbag With These Pieces That Stand The Test Of Time

It wasn't too long ago that the hashtag #teenagedirtbag was trending on TikTok. Thousands of adults created montages of their high school rebellious phases while a sped-up version of the "Teenage Dirtbag" by Wheatus played in the background. Celebrities like Christina Aguilera and Gwen Stefani participated in the trend, reminding fans of their most iconic and angsty Y2k moments. The hashtag includes thousands of posts with throwbacks dating back to the '60s. Despite the range of eras, we noticed one consistency throughout them all — teenage dirtbag style.

While it might be just a phase in life, it is not just a phase in the fashion world. Oversized and ripped clothing will always be cool. Whether you were straight-laced or a wild child growing up, giving your look an alternative twist is always in style. This is especially true today now that the indie sleaze aesthetic is bringing '90s grunge rock vibes back. If you want to keep up with this trend, are feeling nostalgic, or are in your villain era, we've listed some teenage dirtbag staples you might want to consider adding to your closet.

The alternative band tee

What are your teen years if not competing with everyone to have the best music taste? Putting on headphones and blasting music was a telltale sign that you were so artsy you were not to be bothered. While you might have grown out of this attitude, one thing you shouldn't mature out of is the vintage band tee that went with it. Instagram user @taniceelizabeth gave a perfect example of how it's done. Her black shirt reps a trippy alternative band logo, making it the perfect simple statement top to throw on with anything.

Halter tops

If you want a flattering, beachy top for the summer, look no further than the halter tank. Instagram user @michellefleur posted a photo of her and @amaka.hamelijnck wearing cropped halter tops. They look like they're living their best lives, vacationing by the beach in Barcelona. The easy, carefree tank is a great, flattering cut on anyone and can fit a variety of vibes. While @michellefleur wears a triangular sparkly halter, @amika.hamelijnck opts for a sleek nude halter with cutouts.

Bikini tops

Who says bikinis are just for the beach? When you're a teenage dirtbag, customary rules like this get thrown out the window. Instagram user @woseynnaaa's outfit reminds us that if you look good in something, you should wear it — clothing category aside. Wearing a Louis Vuitton bikini top with an open button-down and folded mom jeans, there's no arguing she looks badass. While the luxury brand is a nice touch, you can easily copy this look with any simple triangle bikini top.

Painter jeans

In most contexts, spilling paint on yourself would be an accident. More proper folk would think you've ruined your pants, making them unsuitable for the public eye. But when you make it look intentional, you're just a teenage dirtbag.

 Instagram user @megatronhatesyou wore her painter jeans with a zip-up hoodie and chainlink. If you're feeling crafty, you can even make your own pair. All you need is to thrift some jeans, buy or make stencils of your choosing, and grab some fabric paint.

Oversized leather jacket

If you need grunge inspiration, @rebecaoksana's Instagram page is chock full of incredible outfits that hit the nail on the head. One of her go-tos that is particularly nostalgic of the teenage dirtbag years is the oversized leather jacket. It's a laid-back fit, and it's leather. How much cooler can it get? Pairing a jacket like this with a mini skirt, as @rebecaoksana has in this post, is a great way to emphasize intentional bagginess.


If you saw "Lady Bird" and didn't relate to the main character, it's never too late. You might not want your personality to revert to that of an uncertain 18-year-old who feels like an outcast, but we totally support you if your style does.

Channel your inner angst and get yourself some preppy-looking oxfords. If they are black platforms, you get bonus points in the grunge department. Instagram user @_chaantall wears hers with a monochrome white outfit and thick crew socks.

One-shouldered top

One-shouldered tops have been in trend for a while now. And this is probably for a good reason. The unique asymmetrical line can spice up any simple fit. Instagram user @sophiakelly's all-black look proves this to be true. Paired with baggy 501s, chunky black leather boots, and an alligator purse, the one-shouldered top adds the perfect amount of sultry chic to make her outfit scream femme fatale. This fit can double up for a coffee run or a low-key night out.

Ripped mom jeans

Remember when skinny jeans were mainstream, and 501s were a crazy alternative, retro choice? Those days are long over. However, the mom jean still carries an edginess. If you want to commit to the teenage dirtbag aesthetic, wear your jeans with some sizable rips. The knees or back of the upper thigh are all optimal places for a good tear. Instagram user @jainaazalea wears the ideal pair. They look worn in but are perfectly sized for a flattering fit.

The oversized jean jacket

One thing you'll notice with the teenage dirtbag aesthetic is that oversized outerwear is everywhere. We can't quite pin down why that is, but there's something cool about wearing a jacket five sizes too big. You don't care that it doesn't fit, but with the power of confidence, it somehow looks tailor-made for you. Instagram user @oliviapezzente wears an adorable plaid, sleeveless bodycon dress. She throws a dark-washed jean jacket over it, and voila, the look is dynamic and edgy.

Knee-high cowboy boots

The movie "Footloose" is an iconic romanticization of the teenage dirtbag experience. In a stuffy, small town that's outlawed dancing, a bunch of teenagers does exactly that. The pastor's daughter, Ariel Moore (Lori Singer), is the rebellious main character, and she's seen almost exclusively in cowboy boots. Cowboy boots have a free-spirited, Wild-West nostalgia to them. And, the knee-high, heeled shoes pair with shorts or a skirt for an indisputably stylish look. Instagram user @amoralaini pairs white cowboy boots with a fitted black romper, and it reads as nothing but bold and confident.

Baggy cargo pants

For a long time, cargo pants were for boy scouts and went untouched by anyone who considered themselves stylish. But again, for whatever reasons, the baggier, the cooler. Over the past decade, someone began wearing baggy cargo pants, and just like that, they have become a core part of the cool girl ensemble. Instagram user @rachelxkamm wears a reflective pair, making her cargo pants look a tad bit sporty. Worn with pointy high heels and a crop top, the combination is both edgy and dressy.

The slip dress

From Madonna to Olivia Rodrigo, all of the great teenage rebels of our time have strutted in slip dresses. For older generations, it's considered lingerie, but for teenage dirtbags, it's the perfect sundress. Instagram user @yolandainthecity poses for her feed in a delicate, floral-print slip. With wired cups lined in lace, her dress makes for the perfect flirty, feminine springtime outfit. And for shoes, she is wearing none else than Doc Martens black oxfords — the most classic grunge footwear choice.

Motorcycle jacket

Need we say more? This jacket style has "motorcycle" in its name, giving it immediate teenage dirtbag status. Every '90s ingenue who rebelled from her parents was caught on the back of a motorcycle. Think "What a Girl Wants" or "Chasing Liberty." Whether you're a passenger, motorcyclist, or neither, wearing a motorcycle jacket gives you immediate street cred. Instagram user @themamalopez wears her motorcycle jacket over a simple tank and black leather pants. Combined with black sunglasses and sneakers, she has definitely channeled her inner teenage dirtbag.

Black bodycon dress

When you're crunched for time and don't know what to wear, a little black dress is an easy option. It's a cliché, but a cliché for a reason. If you want to put a teenage dirtbag spin on the LBD, go for a bodycon mini dress. Instagram user @nicollefigueroaa posted a photo showing how this minimalist style can really do the most. Her fiery, gorgeous hair definitely helps spice up the look, but you can add your own flare with a single statement accessory like a headband or earrings.

The boyfriend cardigan

There is totally a teenage dirtbag spectrum. It's all about rebellion, but on one end, there's the smart, alternative type, and on the other, you have the free-spirited, party animal type. If you lean towards the bookish side, a boyfriend cardigan will be your go-to for just about any occasion. Instagram user @ivy_nicolee's grey, argyle plaid sweater is the perfect example. Worn with a flowy, white skirt, her oversized cardigan captures a style somewhere between bohemian fairy and "I just read 'Catcher in the Rye.'"

Corset top

Wearing a corset as a top has become mainstream over the past decade, so it's easy to forget how transgressive the look originally was. Like the slip dress, older folks consider the corset a scandalous undergarment. Cinching in your waist and highlighting your curves, the corset is definitely on the sexier side. But considering how adorable it looks, it should by no means be kept out of the public eye. Instagram user @oliviagraceherring wears a white corset top with a long flowy, pink skirt, accentuating her silhouette and looking ready for a day in the tropics.

The school skirt

Schoolgirl skirts are a closet staple of the teenage dirtbag. They are traditionally intended to be a preppy, bougie part of private school uniforms. But when these mini skirts are put into streetwear, they add the perfect flirty edge. Combined with not-so-preppy attire, they become a symbol of rebellion against the stuffy institutions the design came from. What could be more angsty? Instagram user @katiehoylee wears her khaki school skirt with a fitted jean jacket, platform loafers, and leg warmers.

The letterman jacket

Ah, you thought we were done with the oversized jackets! We swear this is our last, but we guarantee it is definitely not the least. The letterman is a standard American high school jacket. It has the design of a bomber jacket but reads as preppy and old school. Instagram user @pollyrosey posted a photo demonstrating how versatile this staple is. Layering this masculine-looking, casual jacket over a long white skirt, she strikes a perfectly stylish juxtaposition.

The bucket hat

Bucket hats were totally designed for enthusiastic class clowns and slackers. There's something kind of goofy and laid-back about the 360-degree rim that signals you don't take yourself too seriously. Since they're associated with '90s rappers, they also carry a kind of swagger. Instagram user @by.regiina wears her bucket hat with a bikini top and open button-down. It's the perfect accessory when you want to add some character to your look.

High-top sneakers

If you don't already have a pair of high-top sneakers in your closet, we commend you for your creativity because these are the kind of shoes you can throw on with everything. They can be dressy, casual, and everything in between. They give skater vibes, and how can you think of teenage dirtbags without thinking of your high school's skateboarding crew? Instagram user @angelahenche pairs her white Nike high stops with loose-fitting cream-colored jeans and a white crewneck for a relaxed monochrome fit.