Playing Dress-Up

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Lil' Gypsy owner Sam Hart (right) outfits writer Anne Lapour in a 1950s-era cotton sundress. Photo by William Bragg.

Lil' Gypsy, located north of downtown on Broadway Street, has been open for 25 years. Photo by William Bragg.

Lil' Gypsy owner Sam Hart. Photo by William Bragg.

Lapour (right), who says she dreads costume-party invites, had fun letting Hart dress her in several vintage ensembles. Photo by William Bragg.

Photo by William Bragg.

Photo by William Bragg.

Lapour searches for another outfit to try on. Photo by William Bragg.

Hart dresses Lapour in a Victorian-style ensemble. Photo by William Bragg.

Photo by William Bragg.

Photo by William Bragg.

Photo by William Bragg.

Lapour models a navy chiffon dress she tried on recently. Photo by William Bragg.

Photo by William Bragg.

Photo by William Bragg.

It may seem surprising that Lil’ Gypsy Vintage Boutique and Costumes — a collection of the eclectic and whimsical that looks like it might be more at home in Portland’s Hawthorne District — would survive in Salem for 25 years. But Salemites keep coming back to the shop, and it doesn’t run on Halloween alone.

Much of Lil’ Gypsy’s success seems to be a result of its owner, Sam Hart, 53 — a native Oregonian known by many simply as “Gypsy.”

When I sit down with Hart to discover what makes her store so special, she assures me, “I’m not as interesting as people think I am.”

A Gypsy Makes Her Start

Hart is definitely interesting, but not necessarily because she makes hats that blink, or because her shop boasts a drawer labeled “miscellaneous noses.”

Though she found fashion “fascinating” as a young girl, Hart never indulged the dream of a fashion career. “It was complete survival,” she says of her life growing up on the Oregon coast. “I had my daughter at 15. …. I didn’t make it through high school; I had no education. I really was destined to not do well.”

Hart found inspiration through being a mom. “I wanted to show my daughter that I could somehow provide for us,” she says. “I’m one of those people who believe you have to spend money to make money. And a gamble on your future is probably the wisest gamble you can take.”

And what a gamble she made. In the early 1980s, one of Hart’s friends offered to sell her his entire thrift store on the coast, but she had no money, so he suggested a trade: everything in her house for his store. She agreed.

“He took everything,” she tells me. “And I walked into a turn-key vintage clothing store. My daughter (who was 4 or 5 at the time) came home from school and was like, ‘Where’s the TV? Where’s the couch? Where’s my bed?’ And I said, ‘Well, we don’t have those things anymore, but we do have this business.’”

Though that business ultimately failed, Hart’s gutsy move became the impetus behind a pivotal four-year stint living in Florida. “I needed to go (somewhere else) for a while, and I needed to learn things,” she says.

In Florida, Hart worked in high-end boutiques, often dressing wealthy women accustomed to top-notch customer service, and she also learned about “visual merchandising” — experiences she needed to come back to Oregon and try her hand again at running a shop.

She moved to Salem with business sense and a storage unit of about 1,000 costumes left over from that infamous trade (plus others she’d collected). She’d learned previously that Halloween costume rentals make good money, so that’s how it started in the fall of 1989.

“Lil’ Gypsy is the name (of the shop) for a reason. … I didn’t intend to be here for 25 years. I thought I was just going to come in, put my costumes around, have some Halloween money … (then) put it all back in storage and be done. … That’s not what the universe intended.”

Hart Wants You to Feel Hot

Hart wants everyone — from the mayor to a teenager looking for a vintage prom dress, whether they love or loathe dressing up — to have a first-class experience in her store, just like the upscale customers she met in Florida. This, more than anything, may be what makes Lil’ Gypsy so successful.

“I’m all for letting people just browse in the store. But when people need assistance, this is my job. … In our society, I feel like you have to go really high-end to receive good customer service. It’s something they don’t even teach anymore. It’s not important to the retail industry like it used to be.”

According to Hart’s friend and longtime Lil’ Gypsy volunteer Sara (she goes by “Simply Just Sara”), Hart puts her passion into practice. “From the very moment someone walks in, they are treated with both interest and respect, and, most importantly, a curiosity. (Hart) simply cares, and is willing to spend the time to help someone see so much more than what they were thinking about when they came into the shop.”

As an illustration of this point, Hart describes a hypothetical customer who enters the store unenthused. “They’ll say, ‘I’ve got this theme party,’ and I’ll be like, ‘Okay! Let’s rock this theme party!’ Within a few minutes, they’re standing in front of the mirror and they’re like, ‘I look pretty good.’

“And they’ll say, ‘Now I’m kinda excited about going to this theme party,’ and I’m like, ‘Yeah, you should be, because you look really hot.’ I’m not gonna let you out the door if you don’t look really hot. … I would hope someone would do that for me, too.”

Who Shops at Lil’ Gypsy?

If you find yourself at Lil’ Gypsy just once, chances are you’ll be back. It’s simply too fun to stay away. But who shops there in the first place? And why?

In addition to year-round theme parties, Hart also gets business with prom season, and she says summertime is busy with people looking for get-ups before going to the Oregon Country Fair, Burning Man or Faerieworlds. And then there are those unique occasions that don’t fall under a season.

“(One woman came in) because they were doing a movie and she needed white gloves,” Hart says. “There’s the pirate thing. And how are you going to dress steampunk in Salem if you don’t somehow end up at Lil’ Gypsy?”

I’m not gonna let you out the door if you don’t look really hot. I would hope someone would do that for me, too.

This window into different subcultures of Salem is something that Hart appreciates about her work — she sees a side of the city that many don’t.

“I’m really fortunate because the type of business I have draws those people to me,” she says. “It’s not a big surprise to see a group of women in here all dressed in Victorian clothes because they just had tea. It’s not a surprise to see a rock band from Europe over here diggin’ ’round in the men’s vintage stuff. It’s not a surprise to see a whole group of girls all dressed in crazy clothes like ‘Grey Gardens.’ … They’re a riot; how can I not love that?”

Hart’s finds haven’t just made their way around Salem. “My clothes have gone to some crazy places,” she says, including a Hollywood awards show and even a feature film called “Cheri”starring Michelle Pfeiffer and Kathy Bates.

As for her own “sense” of what people will be looking for, Hart admits she’s still learning. “Over 25 years, there’s certain things I’ve always loved and always thought were amazing, but I couldn’t for the life of me get anyone to look at them. … Now they’re slobbering all over them. Every time I turn around, something has become really hot in this industry. And I’m like, ‘When did that happen?’”

But once it’s popular, Hart has the difficult task of keeping her store stocked with the “it” vintage craze. It can be tough to meet the demand, as she’s learned while trying to dress Salemites for the current theme party trend: “Great Gatsby.”

Flapper dresses aside, what costume request is the most challenging? Hart’s answer is immediate and passionate. “Hands-down, I’m telling you — it’s superheroes!” she says, laughing. “Nobody looks good in Spandex!  You invite 50 people to your party, and how many of those people do you really want to see in Spandex?”

The Lil’ Gypsy Experience

Clearly, customer service is Hart’s bread and butter. So when she asks if I’d like to try anything on, I say yes. I’ve never worn vintage clothing, and I’m one of those people who dread the costume-party invite. Not to worry. Hart is up to the challenge.

First, she asks me to browse. She wants to see what I’m drawn to — type of garment, era and style. This is typical, she says, of how she works with customers. “Sometimes I ask, ‘How do you want to feel? Do you want to be funky, classic, do you want to mix and match?’ I just pick their brain a little bit. … The more I know about how they like to feel when they’re in their clothing, the better I can match them.”

It doesn’t take her more than a couple minutes to get a read on my style. “I see you in one of these sweet cotton dresses,” she tells me, pointing to a rack of pastel dresses that look like they’re from the ’50s or ’60s. She’s right, as I’m naturally drawn towards the classically feminine fabrics and silhouettes. But I have a black-tie event to attend, so we focus on cocktail dresses with a similarly classic look and shape.

Then she gently asks if she can take my waist measurement. It’s certainly not a requirement, but it’s in my best interest. Hart explains, “Because it’s vintage — not sized the same — it’s a matter of matching the article to the person based on measurement. …. There’s nothing worse than getting into a dressing room and trying on a whole bunch of stuff that doesn’t fit you.”

When it comes to selecting the outfits I’ll try on, Hart does most of the work. She knows these clothes, and she knows what might work on my body better than I do. She selects several dresses, including a few I definitely would have passed over. “Vintage is not necessarily about hanger appeal,” she says. “Nine times out of 10, the ones you pass by are the ones you’d actually wear and that would look good on you.”

Hart also busies herself selecting shoes, jewelry and other accessories. She wants to dress her customers head to toe.

Vintage is not necessarily about hanger appeal. Nine times out of 10, the ones you pass by are the ones you’d actually wear and that would look good on you.

I’m a little astounded that I love nearly every dress she’s selected. I narrow down to two options, unable to decide. One is a classic black cocktail dress from the early ’60s, hourglass in shape, with a hint of lace. The other is a ’50s-era navy chiffon, and a bit more elegant. Both need zero alteration, which is rare for me. What to do?

“You stood a little taller in the first dress,” Hart says of the black one. So I take it — and the price is reasonable for a dress that fits me like a glove and makes me feel good.

I’m not the only one impressed by Hart’s skill in finding the perfect ensemble. Lil’ Gypsy customer Jane Adams will never forget the time she first walked into the store, armed with a seemingly impossible request.

“I was in a desperate search to match the exact color of a particular ribbon for a maid of honor dress. … I’d been to just about everywhere I could possibly think of in the Mid-Willamette Valley before going into Lil’ Gypsy.

“Sam just began throwing questions my direction, trying to get a feel of (my goal), and (quickly) found dresses for me to try.”

The result was, as usual, successful. “To my surprise, my dress was there, just needing a bit of alteration. … The whole ordeal of trying to fit into a dress that was perfect for this particular scenario seemed almost impossible, and yet Sam made it feel so easy. … She made a very stressful situation very fun.”

When Adams needed a 1940s-era dress for a recent costume party at the Reed Opera House, she headed back to Lil’ Gypsy.

Falling in Love with Salem’s Diversity

Hart knows Salem is an unlikely locale to build an offbeat business like hers. “We’re not Portland; we’re not Eugene. … But, you know, there are so many diverse people in this town. I fall in love all the time with my customers. How can I not?

“I love their age, their wit, their uniqueness and the crazy way that they wear their clothes and the funky things that they have; their lipstick and their blogs and their friends.”

And Salem clearly has a taste for vintage, which she appreciates. “I think the people who like vintage stuff are really just old souls,” she says, lumping herself in with that group.

So with a successful business and a community she loves, will this Lil’ Gypsy ever pick up and move on? Hart says she’s leaving it to destiny. “This is my truth: I believe the universe guides you to whatever you’re supposed to do. … I say, ‘Universe, you’ve taken care of me so far. You just tell me where I need to be next, and that’s where I’ll go.’”

Sara believes there will always be a demand in Salem for what Hart offers. “Her niche — the unique, the diverse, the fun; the best of what life can offer; a little closet of wonderful things you always wanted to have — it can be yours if you simply push open the sticky door and say ‘hi’!”

About Lil’ Gypsy

Need a costume? Want to delve into vintage fashion? Lil’ Gypsyis located at 1389 Broadway St. NE. Hours are Tuesday through Friday, 10:30 a.m. to 5 p.m.; Saturday, noon to 4 p.m. Keep track of Lil’ Gypsy’s latest inventory on Facebook.

Anne Lapour is a freelance writer, stay-at-home mom, lover of all things vintage, and former costume-hater. She wore her new (old) vintage dress to a black-tie dinner and had a blast.

Partner to Jeani, parent to Liam, William Bragg is a professional photographer. WilliamBragg.com.