My love of vintage clothing did not begin gradually. It started with a dress: a perfect 1950s party dress, made of heavy black-and-pink silk, with a row of tiny buttons down the front. It was $15 at Value Village, it was exactly my size, and I knew when I found it that I wanted to dress that way every chance I got.

I’m obsessive by nature (I know more about Buffy the Vampire Slayer than some people know about their own relatives), and the world of vintage offered no shortage of detail to fixate on. I started shopping secondhand almost exclusively, assembling a wardrobe that ought to belong to a librarian in 1958. I also bought things I was never going to wear–things that didn’t fit me, that were fabulous but not in keeping with the look I was cultivating for myself. They started to pile up.

So I took them to the vintage shop near my house and sold them for a few extra dollars. Once I’d done that for a while, the owner of the shop offered me the chance to consign, which meant a little more money and an excuse to buy every last pretty thing. Soon I was consigning enough that — along with the Etsy listings I’d begun posting — I was seriously thinking about opening a shop of my own.

But the logistics were intimidating. The retail rent market in the DC area can be described as ‘robust,’ but would be more accurately described as ‘fucking insane.’ I would have to buy fixtures, racks, a jewelry case — I would have to learn about vintage jewelry. I would have to accumulate more stock than I’d ever had on hand before, and I’d need somewhere to put it while I looked for a space.

That was when the owner of the shop I’d been consigning at offered me the chance to rent her basement. It was perfect: formerly the men’s and sale department, the basement hadn’t been bringing in much money. Another woman was already renting half of the upstairs, an arrangement they’d been happy with for years. And I could dip my Mary Janes in the shallow end of the brick-and-mortar pool.

I started accumulating stock. I thrifted like it was my job (and hey, it was!), I scoured estate sales, and my boyfriend told me about a wholesale ragger in Baltimore that sounded incredibly promising. In a month I spent $1500 on over 300 pieces of clothing and accessories. They piled up in trash bags in my living room while I hunted for more.

It’s been a year and a half, and I think I can say with confidence that it’s been a success. It’s definitely still a part-time job — but then, I still put in part-time hours (about 15-20 a week on average). For those who want to get into the vintage business, I can recommend my path without reservation.

There are caveats, though. Not a morning person? Well, learn to love your coffeemaker, because if you don’t get to that estate sale an hour before it opens, some senior citizen is going to snake all the good stuff. It helps to like people, and like listening to them: your customers, the people you buy from, the contacts you make. You have to be able to encourage a customer into seeing she’s got the curves for that wiggle dress, or gently persuade an elderly hoarder to consider letting go of her college wardrobe. Sometimes I feel as much like a therapist as a saleswoman, or a buyer.

One things that’s vital to any part of the vintage business: you have to have a digger’s instincts, for stuff and for stories. Developing an eye is important– at this point, I can walk down a thrift-store rack and pull the one piece that’s worth anything without much more than a cursory glance. But sometimes you do have to dig for the best stuff, and dig harder to find out where it came from.

Fortunately, a lot of people are going to want to tell you the stories behind their stuff. I think a lot of them don’t like the idea of their things becoming anonymous, separated from their context. So with a little prompting, you can find out: I wore this to my Sweet Sixteen. This was my mother’s. She never married, and spent all her money on clothes.

The hardest part, at least at first, is finding worthwhile stock. If you focus on thrift stores, you’re going to feel like you’re drowning in a horrible sea of polyester. If you go mostly to estate sales, you’re going to be bleary-eyed from early mornings. There are other methods, but they take time and networking.

Foster contacts with the people who have access to caches of clothing, so you don’t have to go through the intermediary of the thrift store or wait in line at the estate sale. Make friends with other dealers. Contact people who clean out hoarder houses or move seniors to assisted living. Get business cards and hand them out like candy. When you find stuff that’s good but isn’t in your wheelhouse, pass it on to another dealer — when they find stuff they know you’ll love, they might return the favor.

Networking with other dealers, by the way, is probably going to mean meeting some interesting people. Most of the vintage dealers I know are lovely, but they’re also kind of a bunch of Miss Havishams. I mean, the Victorian wedding gown is for sale and all, but we are, collectively, a bunch of weirdos.

There’s the tiny little old lady who sells vintage out of her home, which is so stuffed with clothes that I’m not sure where she keeps her husband. There’s the owner of my shop, who basically runs the Island of Misfit Dogs and might drown in unmatched clip earrings one of these days. There’s the lady who (allegedly!) was caught at an estate sale with price-tagged vintage stuffed under her sweater. Normal people don’t get obsessed with vintage clothing, as far as I can tell.

Our customers are as varied as the people we buy from. There are the hard-core vintage lovers, who’ve mastered the pin-curl set and drive classic cars, but they’re not in the majority. There are fashionistas who want to look edgy and unique, and pair their vintage finds with the trendiest possible accessories. Some people just want a suit to wear to work, and know that Pendletons never go out of style. And, of course, there’s an endless stream of people going to Mad Men parties and Gatsby parties and Seventies parties, who might not ever wear that piece again.

Selling to all those people means becoming a walking encyclopedia of fit and style. I can size up a customer pretty quickly, at this point: got narrow shoulders and big hips? It might seem counterintuitive, but a full, high-waisted skirt is your friend. If you’re built more up-and-down, look to the ’20s and the mid-to-late ’60s; the ’70s produced plenty of cute A-line dresses that look good on curvier girls. Try a brightly-colored slip under that sheer dress, or a rhinestone necklace with that sweetheart neckline. Trust me. You’ll look great.

There are things I have to bite my tongue about, though– I’ll speak up if something doesn’t look good, but some customers want things I can’t give them. The stuff you think of as typical, for a given decade, is usually something high-fashion, trendy, and hard-to-find in real life. We don’t have a closet full of Pucci minidresses, or a rack of beaded flapper gowns in wearable condition. I’ve never seen a real poodle skirt, and neither has any dealer I know. And no, we won’t let you try on the hundred-year-old silk gown, mean French lady who always makes a mess of the dressing room and then tries to haggle. We know better.

Here’s the truth: the older something is, the smaller and more fragile it’s likely to be. If the original owner wore a corset or girdle to get into it, you might have to do the same. We look hard for plus-size vintage, but it’s tough to find and gets snapped up quickly, while the tiniest dresses linger on the rack. The oldest, prettiest, most delicate and lovely stuff is usually the least wearable. This business is full of heartbreakers: dresses too small for anyone over the age of twelve, or so heavily beaded that the shoulders are giving out, or stored in a damp basement for too long and ruined forever.

We keep digging, though, because there’s nothing like walking into that one perfect estate sale an hour late– the one where nobody’s gotten there first, and every closet is packed, and everything costs a dollar. And there’s nothing like watching someone come out of the dressing room in the dress they’re going to wear to their prom, or their wedding, or even just to work. It’s a good feeling, knowing you’re giving these things a second life, that people are going to make new stories around them. That, if they survive, someday someone else will wear them, that they’ll mean new things to people you’ll never know.

That’s a pretty good feeling.

The model pictured is Grace Luo. The photographer is Deanna Edmund.