Written by Sammy Aronoff

In today’s market, for some vintage clothing might be a smarter investment than stocks. While the stock market fluctuates unpredictably, and meme coins rise and sink into oblivion before you can eat breakfast; the demand for rare and nostalgic fashion continues to go up, with pieces from the early 2000s Y2k movement, archival designer, and classic workwear fluctuating in price every year. If you know what to look for; holding onto the right vintage pieces could yield better returns than your neighbors portfolio.

Vintage is off to an incredibly hot start in 2025; riding the wave of 2024 prices have continued to rise. New trends are popping up and in classic cyclical fashion, trends fade into oblivion. Five years ago JNCO’s were not on most pickers radar when thinking high value holds, but now if you can get your hands on a pair for a reasonable price its an easy flip when even the worst cuts fetch $125+ on all platforms. From Denim to T’s this is the buyers guide to the early “Buys” and “Sells” of 2025. 

Item 1: True Religion  

Chief Keef has a song named “True Religion fien” 

Market Trends

bloodywingedangel on Depop

True Religion has been on a massive resurgence, riding the Y2K and early 2000s nostalgia wave. Celebrities like Bella Hadid and Travis Scott and many more have all been spotted wearing the classic Double U, their baggy silhouettes, thick contrast stitching, and iconic horseshoe pockets align perfectly with the current trend cycle. Additionally, brands like Chrome Hearts and Kapital have taken inspiration from this era, further cementing the relevance of early-2000s denim.

A few years ago, you could find True Religion jeans for under $20 at thrift stores, and probably around $30-$40 on sites like Ebay and Depop, but in recent years prices have really skyrocketed. Well-preserved pairs, especially flare and baggy fits, regularly sell for $100-$200, with rarer styles fetching even more. While prices are still climbing, the market is becoming more saturated, with more people flipping them. Shoutout Kendrick for wearing a pair of Celine flares during the Super Bowl Halftime show; my prediction is that this drives up prices of similar wash and bootcut styles which True Religion has produced plenty of throughout the years. 

toothtaker on Depop

Verdict: Buy (But with caution)

True Religion still has room to grow, but not every pair is a goldmine. Stick to standout washes, baggy fits, and limited or collab pieces. Avoid overly common styles, as the hype may cool down within the next year or two. If you’re holding a pair, it’s not a bad time to sell, but there’s still some upside if Y2K continues dominating. If you’re looking to make some quick cash I wouldn’t blame you for selling but if you’re looking for a bigger pay day, but don’t be afraid to hold.

Item 2: Vintage Nike ACG 

Market Trends

Nike’s ACG line has always been about creating a balance of outdoor functionality with a bold street style that is instantly recognizable. Since it’s creation in the late 80s, ACG has steadily become one of the most interesting vintage collections for sneakerheads and streetwear enthusiasts alike. Mixing the classic designs of GorpCore with new and innovative fabrics and colors along with the implementation of GoreTex. When the collaboration with Supreme dropped, ACG hype skyrocketed but since then has evened out back to a more reasonable price. Over the years, the vintage ACG pieces have become highly sought-after due to their aesthetic, durability. It should also be noted that the rise of GorpCore has also dragged many ACG pieces up in value. 

Nike hiking – 1981 saw the introduction of Nike Hiking. The often forgotten predecessor to ACG, this small range featured the tough Lava Dome trail shoe, alongside both the Magma and Approach boots.

With the rise in popularity of technical outerwear and retro sportswear, ACG’s vintage designs are now among the most coveted items in both the fashion and outdoor gear markets. From the iconic ACG Mowabb sneakers to the oversized jackets, collectors are always on the lookout for high-quality pieces in excellent condition.

Verdict: Buy

Here are some of the reasons why I consider ACG a good buy when thinking long term holds. First, they’re incredibly rare, especially in good condition. Due to the wear and tear these pieces have gone through over the years, finding them in pristine form is a challenge. When they do pop up, they’re usually snapped up quickly. Second, Nike’s collaboration with artists, designers, and influencers has injected new life into the ACG brand, further pushing up the value of vintage gear. 

If you’re looking to invest in vintage Nike ACG, the market is primed for growth. Limited releases and collaborations, like those with Sacai and Undercover, have only amplified interest in older, classic models. Vintage Nike ACG isn’t just a fleeting trend – it’s a solid hold. The line’s cross-market appeal, limited availability, and lasting performance make it a wise long-term investment, especially if you can get your hands on those rare and highly sought-after pieces.

Carhartt Jackets

Carhartt Detroit jackets that once sold for $50-$100 now fetch several hundred dollars, with rare fades or Aztec variations fetching even more. The market has been fueled by influencers and stylists pushing the aesthetic, but with such inflated prices, buyers may start looking elsewhere for affordable alternatives. Think of overpriced Carhartt jackets like a 90s bootleg Hilfiger tee—looks dope at first, but eventually, everyone realizes they overpaid. When prices get too high, buyers vanish faster than a grail on a $1 auction, and suddenly, sellers start slashing prices just to move inventory. That’s economics, vintage-style: what goes up must come down—just like the value of that $1,200 work jacket when the hype fades.

Verdict: Sell

If you’re sitting on a stockpile of vintage workwear(especially non-Carhartt), now is the time to offload. All workwear is at peak price now because of Carhartt hype, and non-Carhartt jackets that sell for 150-200 now will drop out faster then Carhartt, no hate to brands like Dickies, Ben Davis, and even Wrangler but overall workwear has seen an increased demand. This shift causes sellers to raise prices on these once-overlooked pieces, creating a ripple effect across the entire category. Essentially, Carhartt’s inflation sets a new benchmark, making everything else in the workwear space seem like a bargain—until those, too, become overpriced. The market is nearing its peak, and as we move into a new year, new trends are bound to take over. While workwear will always have a place in vintage fashion, prices are likely to level out, making it a great time to cash in before the bubble bursts.

College Gear 

Market Trends 

It might help that I work at a college vintage store but I’ve seen first hand the demand for vintage college gear. In recent years, schools have transitioned to offering merchandise that’s more aligned with popular trends, often featuring collaborations with heavyweights giants in the clothing industry like Lululemon and Cactus Jack. This shift away from a free market means college gear has become more standardized, and the market for vintage or unique items is growing.

In my eyes one of the most interesting trends within college merch is the world of the bootleg, just like with any vintage item bootlegs have always been created and they are often times some of the most interested and well-designed items. College-themed T-shirts, jackets, and hats – especially those that feature vintage logos or old-school graphics also have a dedicated following. Some of the standout items in this space include pro player jackets, like the classic Starter jackets, which were a fan favorite in the ’90s, and now make a huge comeback in a modern, more stylized form.

Vintage college merchandise isn’t just a trend –  in our eyes, it’s a smart investment. The performance of college teams in major sports like football and basketball can drastically affect the value of team-specific gear. The Top 25 teams can fluctuate quickly, and if your team has the potential to rise in the rankings or make a deep run in March, now is the time to keep your eye on vintage college gear. When teams break into the national spotlight, their gear often follows suit, and demand increases.

The key here is understanding the cyclical nature of college sports. Every year, a new generation of students are eager to buy gear supporting their school’s team. Whether it’s jerseys, hats, or that iconic vintage college sweatshirt, there’s always a fresh wave of fans ready to sport their school pride. For those who can identify the potential for teams to break out or have a resurgence in a given season, investing in vintage college merchandise is a solid hold.

Item 6: JNCO’s (Sell Sell Sell)

Market Trends 

JNCO jeans, known for their extreme flared legs and oversized silhouettes, have surged back into the spotlight due to a TikTok-driven craze. But while the hype is real, this resurgence feels like a classic cyclical vintage “bubble” situation – one that may soon burst. It’s important to be cautious with JNCOs right now, as prices are at their highest in over a decade, but this trend shows all the signs of peaking and potentially collapsing, making it a prime time to sell.

Historically, JNCOs were a part of ’90s and early 2000s alternative fashion, loved by skaters, ravers, and rebellious minds. After a long period of dormancy, the brand’s nostalgic value has skyrocketed thanks to social media platforms, especially TikTok, where influencers and fashion trendsetters have made these oversized jeans a statement piece once again.  Everybody has seen their favorite vintage influencer pull a mac book or a kitten out of their comically large JNCO pockets. The fascination with ’90s and early 2000s fashion has seen a flood of old-school trends making a comeback, and JNCOs are no exception.

While the current wave of popularity has led to the highest prices for JNCOs in more than 10 years, there’s reason to believe this trend is nearing if not already peaking in pricing. Trends driven by viral social media moments can often be short-lived, especially when they’re fueled by the novelty factor. Once the buzz dies down, the resale market for JNCOs could drop sharply, leaving those who invested in the hype holding onto denim that’s no longer in demand.

At the moment, there’s a huge opportunity to cash out on those rare, vintage pairs, especially the ones with bold logos or unique designs that are in top condition. The highest prices seen in over 10 years are tempting, but it’s important to remember that when a trend like this is as ephemeral as TikTok, it can evaporate just as quickly as it appeared.

Verdict: Sell Sell Sell 

Cyclical Trends…

For those holding onto JNCOs, the best move is to sell now while the market is hot. The prices are unlikely to hold once the TikTok craze fades, and buyers may soon realize the trend was more of a flash-in-the-pan than a lasting cultural shift. Sell while there’s still a demand, and don’t get caught on the wrong side of a denim downfall.

Understanding how trends cycle is key. With the rise of outdoor and technical wear, vintage Nike ACG has the potential to continue gaining in value, while items driven by the “TikTok effect,” like JNCOs, could peak and drop just as quickly. The key takeaway is to buy with an eye toward sustainability in the market. For those buying or selling, timing is everything.

So, what’s in your collection? What are you buying or selling right now? Are you betting on the next big thing, or playing it safe with items that will stand the test of time?