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Claire Danes covers the July 1998 issue of Vogue, shot by Steven Meisel. In the interview with Jonathan Van Meter — does Vogue just keep him on some kind of Hollywood starlet retainer? — she is set to start at Yale in the fall, and confesses she's nervous she'll get kicked out. Amy Astley is still the beauty director, years away from launching Teen Vogue. In her "Letter from the Editor," Anna Wintour bemoans the fact that the April issue, intended to be a tongue-in-cheek "guide to the fashion establishment," had been taken rather seriously in the industry, even reportedly costing an unnamed design house their financial backing for not making Vogue's list. There is an ad for HBO's newest show, "Sex and the City." In several places, Vogue predicts the biggest trend — sparked by Marc Jacobs's debut collection for Louis Vuitton — will be logomania. 

I read this issue cover-to-cover, more intently than I've read any issue of Vogue in a long time. And this funny little time capsule hasn't been in my possession for nearly two decades; I bought it on eBay, new and still in the sealed mailing bag, for $5.99 plus shipping. 

That would turn out to be a steal. Over the course of a few days, I put offers in on nine issues of Vogues from the '90s and early aughts, paying anywhere from $2.50 (Sarah Jessica Parker, August 2003) to $20 (my Holy Grail: Gwyneth Paltrow, September 1999) for each issue, with most hovering around $15. When you consider than many of these issues retailed on newsstands for $3, that's quite the return on investment.

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So, who, exactly, is selling these magazines? Matt Oran is one seller on eBay who specializes in the field of paper collectibles, a business he followed his dad into after leaving a job at the New York Stock Exchange; he sold me the coveted Gwyneth Paltrow issue. It all started for the duo when a friend sold the elder Oran 30,000 copies of Life magazine. 

"I went on eBay, and see just a random Life magazine that we're selling for a dollar — or 50 cents even — and it's going for 20, 30 bucks," Oran says. "I had no idea about this before he got me into it; like every other person, I had magazine subscriptions, but never thought that this could be a business until I realized we have 30,000 of something that might be worth 20, 30 dollars each. And based on what he paid for it, it's actually a tremendous markup."

From there, Oran began to branch out, selling old copies of The New Yorker and People before landing on fashion magazines. A family friend's father passed away, and he had owned a magazine store in New York City. When Oran went to buy some of the old stock, he learned what so many of us in the industry already know: Fashion loves to repeat itself. 

"[My friend] told me that the fashion world, every 20 or 30 so years, they recycle a lot of the looks, and the main way they were able to do this is going back to a Vogue from the '90s, and what was hot then," he says. "It's funny, right around that time, I lived by the Jersey Shore, and I started seeing all these girls wearing cutoff jean shorts, which might have been popular when I was young, and looking at some of my '80s and '90s magazines, that was a popular thing. So it is kind of funny how the trends go."

That's certainly one reason that many people buy back issues of fashion magazines, but it's hardly the only one. Set designers will often buy back issues of magazines, sometimes in bulk, to set the scene for a period show. Oran says he's also sold to celebrities — he suspects Uma Thurman created an eBay account to buy nine back issues of magazines she covered — as well as to historical societies, museums like The Met and the Smithsonian and to people trying to find issues in which a family member might have contributed or featured, or to which they just felt a connection. "A lot of this stuff is reuniting people with memories in the past, and I really enjoy that part of it," he says. "You feel like you're making somebody's day."

My friend Jenn Werkhoven, who also works in fashion, began collecting old issues of Seventeen for just that reason; she started by trying to hunt down an issue featuring an anime-inspired editorial. 

"I had always been really into fashion but also video games, and seeing a bunch of cool plastic accessories with this crazy cartoon aesthetic was the first time I realized those two things could exist in harmony," she tells me over email. "This was in 1997, a year before Pokémon came out in the U.S., so that aesthetic had not full entered the public consciousness yet. I had really specific memories of reading this issue while watching MTV at my best friend’s house after school, and it blew my ninth-grade mind!"

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That one issue lead to a full-blown collection of copies acquired on eBay. Werkhoven bought most of them in lots working out to a cost of $5 to $10 an issue; buying individual issues can be more expensive because of shipping costs. But she's also started buying old Delia*s catalogs, which is a much more costly hobby: Issues usually run her about $20, but "in a fit of frivolity" she's paid over $100 for a single catalog, and she's seen them go for even more than that. "Early Delia*s is much more difficult to get," she explains. "Since it's a catalog and not a magazine, I guess people didn't save them and the supply is much lower. Or they don't realize there is a market for them and thus don't try to sell them."

Just how does pricing on these back issues work? Because there's not a solid market for it, it's more of an art than it is a science. First and most obviously, if there's a big celebrity or supermodel on the cover, it will command more. "I would definitely want a celebrity cover over not a celebrity cover, especially in a key-word search," Oran says. Age is another big factor, with pricing going up as issues get older and harder to find. It also depends on how much the seller paid for it; buying in bulk from the same seller can also help bring down costs. (Oran suggests looking for ones with the "Best Offer" option on.)

Bigger issues, like March and September, can command more. And if an issue is famous for any reason, it will also command high prices. Oran says that, at one point, the September issue of Vogue starring Sienna Miller — made famous, of course, in "The September Issue" — was going for $100, and Anna Wintour's first issue of the magazine can also go for eye-watering figures. Most crucially, condition plays a major factor in pricing. Unsurprisingly, it can be incredibly difficult to find magazines in near-mint condition.

"Seventeen is easy to find. It's a mass-circulated magazine and isn't really a collector's item, so there's a bunch of them floating around," Werkhoven says. "[But] since it's a teen magazine it can be really hard to find copies that don't have photos of all the 'SO DREAMY' '90s heart-throbs cut out —presumably to adorn someone's algebra notebook or bedroom wall — or have hearts and rainbows drawn all over the pages. For me that kind of adds to the charm."

As one might expect, thicker magazines that publish less frequently can also go for higher prices; older issues of magazines like Love and CR Fashion Book can demand up to four times for which they originally sold, depending on the cover star. "Biannuals are always more collectible, I think," says Katie Grand, editor-in-chief of Love. "We can do a 'best of' the season, which is always nice." Thanks to limited distribution, book-like heft and high-profile editors like Grand and Carine Roitfeld, holding onto these magazines can result in a pretty decent sale down the road. But simple magazines like Vogue might have the best resale value; Oran says he's happy if he gets around $30 for a back issue, which 10 times the cover price.

If you're kicking yourself over throwing your old issues of Vogue in the recycling, don't: Individual sellers aren't big movers of back issues. Many, like Oran, are in the paper collectible trade. They're buying their stock at estate sales and auctions, or find sources through word of mouth. Often, sellers have to travel long distances to pick up their bounty from people who just want to get rid of the collections that are clogging up their homes. "Sometimes, I'll try to make it into a getaway or a mini vacation type of thing," jokes Oran, who was driving to Boston and back to drop off a big sale the day after I spoke with him. 

Oran currently has nearly a thousand old copies of Vogue, including international editions, for sale at his eBay store. But, as you've heard a million times, print is dying — and the secondhand market is no exception. "Honestly, I've really seen a big slowdown on everything," Oran says. "Vogue, for instance, was one of my best; I would sell probably a Vogue every other day. Now if I sell one every two weeks I'm happy." (In case you're wondering: The New Yorker and Billboard still do well for Oran, with fashion magazines coming in third.)

Still, with nostalgia firmly taking hold of the fashion industry, these little gems may have life in them yet. Digging through my '90s Vogue haul was a pleasurable experience, like reading mini-fashion history books. Werkhoven keeps a spreadsheet of the Seventeen issues she's still missing, and she's thinking about expanding her collection to include Jane and Sassy, too. (For fellow fanatics, Werkhoven scans her collection and posts them to her Twitter every week, even learning some programming to build an app that would make the process faster.) Even if you're not planning on holding your magazines for 20 or so years to flip them down the road, they will always be a useful reminder of where we were as a culture as things change rapidly around us.

"God knows what magazines and digital will even be in 20 years, " Grand says. "Magazines might cook dinner and do the dishes, which would be ideal!"

Homepage photo: Whitney Bauck/Fashionista

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