The bag in every celeb’s elbow crutch in the early aughts was relaunched this year by Balenciaga, but some critics (myself included) would argue the original style developed by then-creative director Nicolas Ghesquière is the ideal: The hardware is chunkier, and the leather is crunchier. Bags are also a safe bet to purchase pre-loved, because most leather looks best after some wear and tear. Rebag has dozens of options across sizes and colors, but we’re partial to classic black, just like Kate Moss.

While you can pick up a new corset from the brand, the vintage styles have much more oomph with tartan and lace options that embody Westwood’s aesthetic at her zenith. Some of the rare runway grails from the ’90s clock in at several thousand dollars a pop, but for the everyday consumer, eBay is rife with affordable styles like this gingham wrap corset top.

There’s just something about a slip dress from the early 2000s — just ask Bella Hadid, who keeps flirty vintage Roberto Cavalli dresses on rotation. The fabrics from brands like Cavalli are meant to last if you take care of them correctly, unlike the poly-blend versions being hawked by contemporary designers that will only get a few wears.

If the price of modern timepieces makes your head spin, the secondhand market is flooded with virtually all brands and styles. Well-worn watches are literally less flashy than brand-new ones with a lived-in feel that doesn’t scream “I just dropped $10,000 on a Rolex.” A resale piece will still leave you a few thousand bucks poorer, but this Pasha watch is half the price of the 2024 version.

Much like the City bag, I believe leather shoes age like fine wine; scuffs and stains are encouraged. Consider some used Gucci horsebit loafers, which not only check the preppy-trend box off but can be found up to 90% off current retail price.

Hermès’ vintage designs range from leopard silk scarves to mini twillies originally made for wrapping around Birkin handles that can be worn around the neck, too. Vintage styles are like collector’s items and don’t often get reissued, so buying an older print will ensure you’re unlikely to match with another headscarf-wearing street-style superstar.

This one may seem like a no-brainer, but it bears repeating that Levi’s 501 silhouette is the platonic ideal of denim, with its butt-lifting, leg-sculpting fit and unmistakable blue hue. Used pairs have character you can’t buy new, no matter how shredded they are on the sales floor. While I’m hesitant to recommend buying something so personal over the Internet, I was put onto Jean Genie by Jenna Lyons, unofficial ambassador for 501s, and I’ve been fiending over its curated drops of gorgeous blue jeans.

TheRealReal’s 2024 Resale Report found that used Chanel handbags were the No. 1 searched item of 2024, and with good reason: The retail cost of a brand-new Chanel flap bag has more than doubled in the last 12 years. Pre-loved versions go for thousands less, and vintage styles, especially from Karl Lagerfeld’s era, are collector’s items in their own right. Channel your inner Lily-Rose Depp with a classic black version, or go for a more colorful, Lagerfeld-designed concoction.

FKA twigs stepped out in New York earlier in August rocking Dior Sport 2 sunnies, and we already found the exact same pair on Grailed. John Galliano’s tenure at the French maison is still top of mind for trendsetters and fashion archivists alike, and newer shield sunglasses are less readily available in today’s retail landscape. The older sporty shades are half the price of new ones, plus come with built-in street cred.

This may be another obvious piece, but not for the Gen Z customer who’s picking up reproduced Fleetwood Mac tees from mass retailers. Rare band tees are often quite expensive, but savvy customers can scour eBay and Etsy for reasonable deals on coveted tour merch. Dua Lipa hit the music-festival circuit in summer 2024 wearing a shredded Sonic Youth shirt courtesy of curator Saint Luis, which inspired our pick for a, yes, still expensive tee, but a worthwhile purchase because it’s the real deal.