The Retro Streetwear Trend is Taking Over 2024: Here Are 10 Styles to Shop

The nineties and early aughts weren't complete without a good ole pair of baggy jeans! It's most definitely a requirement to own several pairs of baggy jeans that you can rotate in your capsule wardrobe if you really want to nail the retro streetwear look, and there's plenty of brands who are some great quality (and affordable) styles you can cop that will instantly elevate your entire closet.

For a full list of baggy jeans, we've got you covered.

If you go back and look at just about any set of streetwear pictures from the late 1980s, 1990s, and 2000s—you'll see multiple occurrences of men (and women for that matter) wearing tracksuits. Whether it was a FUBU tracksuit for the men, or a Baby Phat tracksuit for the ladies, tracksuit were kind of the jam back then. If that era of fashion is making a comeback, that inevitably means tracksuits are too. That means you need to cop one ASAP.

LL Cool J, Run DMC, Ludacris—all of these guys were avid wearers of bucket hats in the 1990s/2000s (and that's just a few of them). To this day we still aren't super sure as to why bucket hats caught on the way they did. They did do a good job shading you from the sun (but so did ball caps for that matter), but the choice to wear them definitely seemed more of a stylistically. Nonetheless, bucket hats being worn outside of the beach are making a comeback. Check out some more bucket hats here.

Bombers/varsity jackets were a statement of the late 80s, 90s, 00s. They are still very much a part of style culture today, but in those years you were almost guaranteed to see five different people rocking a sick bomber/varsity jacket while out and about. With bombers being an essential part of retro styling, we expect to see more people wearing them in the spring and fall—which are the seasons they work the best in from a temperature and comfort standpoint. Check out more bomber jackets here.

On the contrary, a puffer coat is an excellent way to be warm and stylish throughout the course of the ice cold winter season. Puffer coats were also a signature of streetwear back in the 1990s (think Notorious B.I.G around the middle of the decade). The neat thing about puffers is that they provide great ability. Throw them over a nice shirt and you have one look. Take the jacket off and it’s a completely different  look altogether. Investing in a good puffer is never a bad idea. If you need a puffer, consider some options from Canada Goose or The North Face.

Chains and necklaces were an especially big part of the late nineties and start of the new millennium as well. Some folks even went as far as having their own signature chains that they wore every time they stepped out of the house (looking at you Sir Usher Raymond). While you don’t need to go as far as having a name branded chain, a simple one can really work as far as elevating your fit. If you're looking for some good jewelry, or specifically earrings, we've got you.

Oversized t-shirts are a trend that’s managed to remain incredibly consistent over the years, so we can’t exactly say they are “coming back.” However, oversized tees have always been a part of streetwear culture regardless of the era or decade, so adding several more of them to your already vast collection certainly wouldn’t hurt.

The good ole handy Timbs. Of course, it’s pretty much a right of passage to be a lover of Timbs if you are a New Yorker, but during the heyday of retro streetwear Timbs were an automatic regardless of where you lived. You even had the ladies wearing Timberland boots (looking at you Beyoncé and Jennifer Lopez). Definitely cop some Timbs if you want to nail the retro urban streetwear look.

If you really want to take the 2000s up a notch—wear anything Ed Hardy. The brand is associated as one of thee defining streetwear companies of the decade, and wearing them now is sure to elicit an “Ed Hardy!” reaction from casual observers. You might even inspire other people to grab their own Ed Hardy apparel and start a movement. Action, reaction, cause, and effect.

You need a pair of clean white Air Force 1s if you want to embody that Y2K look to the fullest. Nelly didn’t make a whole song about these shoes and drive up the sales for nothing! If you’re really committed to the look you can also rock them with a tank/tee and a bandana, but that just might be a little bit too 2000s if you catch our drift.