We’re Still Not Over the Teenage Dirtbag Trend, So Here’s How We’re Wearing It

It’s probably safe to say we all had a teenage dirtbag phase. Going through a rebellious phase is par for the course during the teen years, and that means taking some risks with fashion. While not every look was a winner, some have managed to stand the test of time.

A little while back, celebrities from Lindsay Lohan to Madonna started sharing photos of their “teenage dirtbag” years, including snaps of wild parities and messy fashion. From the distressed sweaters and baggy pants to the leather pieces that are hopefully stashed away in the back of a closet, these throwbacks were a sign to embrace our inner teenage dirtbag.

Luckily, there are really no rules for the trend, so feel free to make the look your own. For a little bit of inspiration, we’ve rounded up 17 pieces to add to your wardrobe and live out your teenage dream.

A denim trucker jacket is a closet staple that can add a touch of grunge to any look. Style this oversized denim jacket with combat boots and a mini shirt dress.

An oversized vintage tee is essential. Made for an oversized fit, this Daydreamer top is an excellent pairing with some ripped denim and Converse.

What’s better than mesh and fishnet? Mesh and fishnet together in one skirt. Miaou’s Fig Skirt really has it all.

Sometimes less is more. For a risqué yet chic look, style this pinstriped mini dress with over-the-knee boots and an oversized blazer.

A white tank top is a versatile necessity, but sometimes a regular ol’ tank just won’t work. This one from K.ngsley features henley buttons and plenty of shoulder cutouts.

We love a good pair of oversized pants that feel like elevated loungewear. These from Hanifa are lightweight and work well for any season.

Corsets have become a wardrobe essential. This piece in particular is made with 15% elastane and is designed to flatter and hug every curve in all of the right places.

You can’t go wrong with a classic black bucket hat. Not only do they work for the everyday wear, but they also protect your face from harsh UV rays.

A bodycon dress is a wonderful canvas for a grungy look. During the day, pair it with a leather jacket and sneakers, then dress it up at night with chunky heels and accessories.

This skirt may go down in history as my favorite skirt of all time. It incorporates so many of today’s current trends mixed with the nostalgia of a Y2K favorite. With an ultra cropped white tank and your favorite shoulder bag, this look will always be on your rotation.

This shoulder bag exudes timelessness and elegance. Pair it with a leather trench to create an edgy date night look.

A sleek black heel may not read as very rebellious, but the sneaky little surprise in the heel sure does.

Hoop earrings have really made an imprint on our hearts. These chunky gold hoops work with every kind of aesthetic and will elevate any look you’re going for. Plus, they’re responsibly made and handcrafted in Kenya.

This assymetric patchwork sweater is a great grungy investment to add to your wardrobe. Style this with baggy jeans for a quintessential cozy dirtbag look.

For a one-stop-shop look that will make heads turn, look no further than this distressed mini dress from Marc Jacob’s cool Gen-Z sister brand Heaven.

Staying on-trend with one of this years hottest styles, this lace crochet top is sheer and can be worn alone for a sultry look or layered over your favorite bralette or cami top. Who says a teenage dirtbag doesn’t love a floral moment?

This oversized poplin shirt is a wardrobe essential that can be worn from the office to the bar. For a trendier look, style it unbuttoned with a sheer bralette and black denim cutoffs.