This is How 3 Classic Clothes Companies Constructed Their Manufacturers


It’s tempting to think that selling your old clothes on sites like Poshmark or ThredUp will immediately generate passive income that supports your brunch habit and annual rent increase.

But if you want long-term success and a recognizable brand that people return to, running a vintage resale business is anything but easy. It takes work, say small business owners who have done it. But it is possible.

We talked with three vintage clothing business owners about how they got their start, crafted their aesthetic and built their brand.

3 Sellers Making a Go in the Vintage Clothing Business

Sara DiNatale of Lucky 727 Vintage

Sara DiNatale has always loved secondhand clothing, so it makes sense that she spent a lot of time in thrift stores.

At first, she shopped for herself and bought items tailored to her tastes. But over time, she started to recognize what items were popular and trendy, even if she didn’t like them, like a Harley Davidson T-shirt.

“Maybe it wasn’t my aesthetic, but I knew that someone would totally die for this,” said DiNatale, who lives in St. Petersburg, Fla. “I did it enough times that I was like: ‘Why don’t I try this?’”

One of her first sales was a Dooney & Bourke vintage belt that she purchased on a bidding website for herself. When it arrived, she discovered that it didn’t fit. She resold the piece for more than double what she paid.

That was a teaching moment for DiNatale: She realized that there was money to be made in vintage. So she took the profits and invested them back into more vintage purchases that she would then sell.

For those starting out, she says, don’t take money straight out of your pocket. Either sell what you already own or invest what you’ve already earned into something else.

DiNatale partnered with a friend when she decided to officially start a vintage side-hustle. They chose clothing resale app Depop to start because DiNatale felt she knew their market and had a similar style.

DiNatale loves secondhand clothing, so she started a side business selling vintage pieces with a friend in January 2020. Her biggest piece of advice: Know what sells. Chris Zuppa/The Penny Hoarder

If she could do it over, she might not make the same choice. Depop’s audience skews young, she says, and doesn’t always see the value of spending a high price on an item, even if it’s a high-quality vintage piece. On Etsy, DiNatale has found she has a better chance at getting a buyer who understands the quality of the garment, but there is also more work involved with the platform.

DiNatale’s colleague came up with the name Lucky 727 Vintage, a play off of St. Petersburg’s area code. She and her partner chose to make a business name, partially because Depop requires it and partially because they wanted to interact online with customers as a single entity. They also made an Instagram page at Depop’s suggestion, although the Instagram account ended up working out as a separate revenue stream for local customers.

The vintage business is what you make of it, DiNatale said. Since starting in January 2020, Lucky 727 Vintage has sold 200 items, about evenly split between the two co-owners. On average, DiNatale makes about $100 a month in profit, although some months it comes out to much more than that.

DiNatale has learned some tricks:

  • First, make sure your product descriptions have appropriate information, like measurements and garment details. If someone has to message you to ask a question, they may no longer be interested by the time you respond.
  • Keep apprised of any changes to Depop’s interface through a sub-Reddit and watch for algorithm changes that could affect how your merchandise is promoted.
  • Most importantly: Know what sells. DiNatale is an avid Dr. Martens fan, and she knows that vintage Docs go quick and at a high cost. They are the rare item she will shell out for in advance, because she knows she’ll make a return.

Jenna Wu of Nanena Vintage

Jenna Wu didn’t always appreciate her love of thrifting. In fact, as a child, she was ashamed that she had to shop at thrift stores, a necessity in her low-income family.

It wasn’t until she got older that she realized thrifting could be cool. She was inspired by a friend who had an unconventional style but always looked amazing, and almost all of her clothes were thrifted. That turned Wu’s thinking, at the same time she started to look into the dangers of fast fashion and waste.

Now, Wu has come full circle. She runs a full-time business based in Portland, Ore., called Nanena Vintage, a play on her nickname of “Nena.” The perks of running a vintage clothing business are the flexibility — you set your own schedule — and the creativity of presenting and packaging the clothes to make them look as desirable as possible.

When Wu started thrifting for money, she was working in customer service and felt drained by her 9-to-5. Running a thrifting business was an artistic outlet that she actually enjoyed. Her partner encouraged her to pursue it full-time.

In 2019, Wu’s entire income from vintage was $5,000. It has increased since then, but she’s still unable to live independently off the money she makes from Nanena Vintage. Photo courtesy of Jenna Wu

Wu’s style gravitates toward feminine and classic pieces, but she tries to intersperse styles that are popular and trendy as well. She’s always keeping an eye on what people want to buy, but she’s also focused on the quality of the material and the uniqueness of the design. And there’s one thing she absolutely doesn’t do — streetwear.

When pricing, she takes into consideration how much time it takes to find what she calls a “gem” in a sea of mediocre items. All that time spent goes into the price a reseller will charge for a garment.

Wu started by selling her items on Depop and found success. She was selling at least one item a day. But a year in, she saw her sales drop off. She wasn’t sure why — had the algorithm changed? As sales continued to dwindle, she decided to switch to Instagram.

It was a learning curve at first.

“You just have to keep at it and keep going and then eventually people will find you,” she said.

Wu has a money-saving tip for anyone starting out: Create your own shipping labels rather than going to the post office.

And if you do want to go out on your own and make vintage a full-time business, be prepared for it to take time before becoming financially viable. When Wu first started, in 2019, her entire income from vintage for the year was $5,000. It has increased since then, but she’s still unable to live independently off the money she makes from Nanena Vintage. In December 2020, she made $1,200 in profit.

Lesson learned: If you want to transform your vintage clothing business from your side hustle to a full-time gig, save up in advance.

Esmeralda Castañeda of Esme Vintage Shop

For Esmeralda Castañeda, selling vintage clothes was initially a way to make money while in graduate school.

She learned the tricks of the trade by watching Youtube videos from longtime vintage sellers who had gotten their start on eBay. But she wanted to sell on a more aesthetic-driven forum — that’s why she initially chose Depop.

Like DiNatale, Castañeda recommends starting with selling your own clothes rather than buying clothes to sell. The first six months of her business were a lot of experimentation with where to shoot photos, how to style them and what backgrounds were best. But it’s harder to experiment if you’re depending on a return from your investment.

Castañeda doesn’t take her vintage reselling lightly — she recommends looking into when things were made and what to expect in material and fit based on the decade, because fakes do happen. Understanding the history behind the clothing helps to make your products better.

Castañeda doesn’t really have a defined style for the clothes she sells — instead, she tries to do a little bit of everything. Her website has designations for mod fashion, minimalist, romantic and classic. She says she skews more toward the romantic and minimalist side, but that’s largely because of what she finds in her local Indio, Calif., thrift stores.

“That’s the thing with vintage,” she says. “You really can’t dictate too much unless you are going to be exclusive. You’re not going to find enough to make a really good income. You really need to have a broader reach.”

Although Castañeda got her start on Depop, where she has almost 10,000 followers, she’s actually seen more of what she calls “influence” on Instagram. For those starting out, Castañeda recommends starting on Instagram and building a brand there. If you’re not finding success, Depop is a good way to have a built-in audience, but she finds Instagram better for building something long-term.

All three vintage business owners agree that making money with your vintage clothing business is totally dependent on how much you work. Some months, Castañeda says, she brings in as little as $500, while others can be as high as $3,000.

“A lot of people assume for some reason that this is passive income, but it’s not,” she says. “You do have to do something to get the income going.”

Elizabeth Djinis is a contributor to The Penny Hoarder.




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