Ask any vintage or pre-loved fashion enthusiast and they will regale you with at least one tale of an object they either closely missed out on or smugly secured for some unthinkably low price. Oftentimes, that object is a bag, lost or gained at precisely the right moment—critically, when it becomes slightly uncool.
The Fendi Baguette, Balenciaga City and Dior Saddle are all prime examples of Y2K icons that, at some point along the way, became style relics. While some of us were more concerned with getting our mitts on a PS1 (not the game console, the Proenza Schouler bag) or a Mulberry Alexa, a small band of fashion future-seers were buying the former It bags for a fraction of their original prices.
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So, what makes a bygone bag desirable again? "From my point of view the value of an item can increase for a number of reasons,' says Gabriel Rylka, founder of vintage bag platform Break Archive. "The brand might have re-released a similar item or collection, discontinued the bag so it cannot be repurchased, or increased their prices over time. [Or it may be because] the bag is limited-edition and scarcer to find in good condition over time."
See too the TikTok effect, with Gen Zers discovering and sharing early-aughts bags like the Ballet Corset and Gaucho from Galliano-era Dior, the Giselle by short-lived but cult British brand Luella, and Phoebe-Philo-for-Chloè’s Paddington.
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If you wish you’d bought a second-hand Fendi Baguette or Balenciaga City bag before they had a renaissance, read on. These are the six bags you should be buying now, while they’re still (relatively) affordable.
Chloè Paddington
"A bag that I did not expect to resurface is the Chloè Paddington," says Rylka. "The demand for [it] has been huge—[at Break Archive] we sell out almost every time." The padlock-adorned style was first released in 2005, when Phoebe Philo was at the house’s helm, and promptly worn by virtually every early-aughts It girl, from Mischa Barton to Sienna Miller.
The Paddington’s comeback has been percolating since 2023 and gained pace on TikTok through 2024 (buoyed by Chemena Kamali’s debut collection for Chloè, which featured the Paddington-esque Camera bag), and shows no signs of waning. Depop reports a 1,137% surge in searches for the bag since June, while LTK has seen searches soar by 3,000%.
Alexander Wang Rocco
It’s 2004. On one of your regular late-night Tumblr doom scrolls, you happen upon a photo of Mary Kate Olsen wearing skinny jeans, peep-toe platforms, and most importantly. a Rocco bag by Alexander Wang. If you bought and kept it, now’s the time to dig it out of the back of your wardrobe.
At Vestiaire Collective, searches for this studded, pebbled-leather bag are rising by 333% week on week, and judging by the exponential number of TikToks extolling the Rocco’s virtues, its renaissance is nigh (likely helped by the fact that Alexander Wang released the Rocco-alike Ricco bag last spring).
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Prada Bowling Bag
When trying to predict which past-season bags might make a resurgence, look to the men’s collections—they are the first shows in the season’s fashion calendar and can be indicative of what we can expect to see in the forthcoming women’s collections.
Eagle-eyed Prada-philes will have noticed the oversized bowling bags in Prada’s fall/winter men’s collection and started buying the brand’s early-aughts versions.
Miuccia Prada has long favoured this silhouette — see the Boston bag which was first released in 1978 and again more recently — but the styles seen on the catwalk are specifically reminiscent of the bi-colour, panel-detail bowling bags from Prada’s spring/summer 2000 collection. Strike now (pun intended), before the trend takes off.
Dior Gaucho
The Dior Saddle bag is just as desirable now as it was in the early ‘00s, when it was anointed It bag status by one Ms Carrie Bradshaw. But this hasn’t always been the case, says Meg Randell, Head of Bonhams’ Designer Handbags and Fashion Department.
This begs the question, which early aughts Dior bag will be next? Our money is on the Gaucho. Just like the Saddle, it was released during John Galliano’s tenure at Dior, and it has the same equestrian styling but reads a little tougher, more bohemian, and is significantly less pricey at resale—at least, for the time being.
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Hermès JPG Birkin
Increasing in value by 14.2% year on year, a Birkin is undoubtedly a sound investment. For something that is a little different (but still likely to appreciate) consider a lesser-known, slightly less expensive iteration of the bag.
According to Break Archive’s Gabriel Rylka, the JPG Birkin — a sleek, east-west version of the classic that made its first appearance in 2004, at Jean Paul Gaultier’s first show for the house — is fast gaining traction.
"Hermès has just released a mini version of the shape which has been swooping social media," he says. "We have been flooded with requests for this bag—the demand is insane." Rylka attributes the increased interest to both the brand re-release and the popularity of Alaia’s oblong-shaped Le Teckel bag.
Louis Vuitton Speedy
It may not be under the radar per se, but the Speedy shows no signs of losing pace, with searches soaring on eBay, Vestiaire Collective, LTK, and Depop, and Louis Vuitton sharing plans for another Murakami collection (this time, cherry blossoms), in March.
"Recently, we’ve seen the Louis Vuitton x Takashi Murakami collaboration bags surge in value, becoming highly coveted pieces in the vintage market," says Mari Corella, eBay’s general manager of luxury. This year’s collaboration with the Japanese artist has reignited interest in the Speedy, prompting 3.5 searches for the bag every second on the platform.
Mason Henry Howell, aka @thehandbaghistorian, also recommends investing in less-hyped collabs. "I’m betting on the Louis Vuitton x Marc Jacobs [bags] from 2001 to 2012," he says. "If [Vuitton] continues to tap into its archive and bring back these iconic collaborations — and I’m certain they will — we can expect the demand (and value) of the originals to keep climbing."