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

Vintage streetwear is making a comeback like never before

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Can you call something a comeback if it's technically been here for years (ode to Run DMC)? Well, yes and no. Fashion is cyclical in nature, and to that point, there's been times over the past decade or so when 1990s and Y2K fashion has indeed spun its way around the block. However, there's an argument that this current rise and interest in retro streetwear (some prefer the term vintage streetwear) is perhaps the largest its ever been as according to Pinterest Predicts, the term retro streetwear itself is up a whooping +55% to start the year 2024. That +55% indicates a definite surge in popularity as we continue to tread through the early months of the new year. Needless to say, we're banking on retro streetwear being big in 2024, and have put together a guide on a variety of styles you can shop to get in on the trend yourself.

Why exactly is vintage streetwear making a comeback decades after its initial styling hit the scene? This is a loaded question that yields some equally loaded answers, but we have a few ideas. Our first theory? Gen Z and young millennials that get the classification of "zillennials" seems to have a fascination with all things with Y2K. On the flip side, nostalgia also seems to be running rampant amongst those that actually were old enough to experience the 90s and early aughts in all of their glory. Our second theory? Comfort. Seeing as though many of the clothes from the 90s/00s period were baggier/looser, people are starting to prioritize their personal comfort over "looking good through the pain" again.

Additionally some of the SS24 and FW24 runway shows for Louis Vuitton, Dolce & Gabbana, Balenciaga, and more have all showcased looks that are reflective of retro streetwear being a defining trend throughout the remainder of the year at least. Alongside that, more affordable brands like Abercrombie & Fitch and streetwear heavyweights such as KITH, Supreme, and Patagonia have been in their respective 1990s/2000s modes for a hot minute now. Without a doubt, retro streetwear appears to be here to stay, and here are some inspiration you can add to your Pinterest boards to keep up.

RELATED: 2024 Fashion Trends: 10 Styles for Men to Look Out For This Year

What is "Retro Streetwear"?

As we mentioned earlier, retro aka vintage streetwear refers primarily to clothing inspired by streetwear influences of the past. This is widely considered to be the late 1980s, 1990s, and early 2000s when the streetwear scene is general was at its biggest and most popular height. This "retro" period spanned roughly ten to fifteen years (circa 1987ish to 2005ish), and through this era, styles like baggy jeans, tracksuits, Kangol hats, puffer coats, and Timberlands (frequently shortened to Timbs) were among the most dominant styles. Additionally, brands like FUBU and Coogi along with rapper-owned labels such as Jay-Z's Rocawear were a few of the defining brands of that period as well.

1. Get a New Pair of Baggy Jeans

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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.

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A Tracksuit Is Essential

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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.

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3. Consider Adding a Bucket Hat

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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.

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4. Opt for a Bomber Jacket in the Spring or Fall

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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.

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5. Puffer Coats Bring Out Your A-Game in the Winter

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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.

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6. Don't Be Afraid to Accessorize

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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.

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7. An Oversized T-Shirt Works With Everything

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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.

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8. Timbs, Timbs, Timbs

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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.

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9. Throw it Back to Ed Hardy

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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.

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10. Air Force 1s

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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.

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What Are the Most Popular Retro Streetwear Brands?

Let's take a look at some of the most popular retro streetwear brands:

FUBU: Founded by Daymond John and co-founders Carlton E. Brown, J. Alexander Martin, and Keith C. Perrin in New York, FUBU was one of the most popular streetwear brands of the 1990s and 2000s. The brand's peak came in 1998 when they grossed $350 million worldwide in sales along with having some of Hip Hop's most notable names representing them such as LL Cool J., Ludacris, and more.

Supreme: Founded in NYC circa April 1994 by James Jebbia, Supreme has gone on to become what many consider to be the pinnacle of skate fashion. Supreme truly offers it all when it comes to clothing and accessories that appeal to the masses, which is what has been their M.O. since the early years, and has particularly known for their affordable pricing.

Coogi: While Coogi was founded in Toorak, Australia circa 1969 by Jacky Taranto, the brand received a boost in popularity in the 1990s when rapper (particularly the Notorous B.I.G) began endorsing them. From that point, everybody wanted "to stay Coogi all the way down to their socks," and the rest is history as far as their impact on 1990s streetwear fashion.

Where to Shop for Retro Streetwear:

If you really want to get particular in terms of copping vintage styles that were actually made in the 80s, 90s, and early 2000s (not remakes or revamps), here's a few places to check out:

RELATED: 23 Underground Clothing Brands You Need to Know

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