July 2019

The Pink Pineapple: Making fashion fun again

Author: Linda S. Hopkins | Photographer: M.Kat Photography


Jan Davis, Susan Davis and Ellie Smith with the store mascot, Hannah.

For most women, shopping isn’t a mission. It’s an excursion: think mini-vacation, therapy session, and party, all in one! That’s what you’ll get at The Pink Pineapple, where owner Susan Davis makes sure everyone has fun, including her customers, her sales associates, and herself.

“People feel like we are their friends,” Davis said. “It’s like you’re coming to our living room. You want coffee? You want water? If need be, we have wine!”

Customer service is at the heart of The Pink Pineapple, and that means offering just the right amount of assistance. “It’s really fun for us when we get someone in who wants help. But if you prefer to browse on your own, you are welcome to do that,” Davis said. “We’re there if you need us.”

At the same time, you might think of The Pink Pineapple as your safe place to try out a new look or a style you’ve never considered before. “We like it when people get out of the box a little, and we encourage customers to try new styles. If you don’t like it, don’t come out of the dressing room. But it can’t hurt to try it on. And we are honest. We don’t want you to buy something you don’t like or something you don’t look good in.”

Davis takes pride in the way she shops for the store and believes it is the key to a thriving clientele that includes a large local following as well as a bevy of seasonal guests who return to shop with her year after year. “I try to buy things that will look good on almost every body type. I also want it to be a little unusual—not something you will find anywhere else,” she said. “We have a few staple-type things, but if you’re looking for a pair of plain black pants, it’s probably not the place to find that. I may have them, but it’s not my specialty.”

She also differentiates her store by carrying lines that are not available in other area boutiques. “I try to not have the same lines as my competitors. Sometimes it happens, but I try to be different.”

A big focus at The Pink Pineapple is comfort. Everything Davis buys has to pass the touch test: Is it soft? Is it comfortable? In the store now, look for stylish but practical leggings and pants with built-in tummy control; cute, easy-to-wear shoes (sandals, wedges, Espadrilles); cool summer dresses; relaxed cotton tops; and accessories ranging from classic jewelry and handbags to funky statement pieces. Prices are affordable, with tops starting at $49 and almost everything in the store under $200.

Customers near and far appreciate the eclectic mix of apparel and accessories with a limited quantity of each design that ensures a one-of-a-kind shopping experience and perpetuates a fresh and ever-changing selection. “I try not to repeat myself,” Davis said. “If I have this shirt this week, when it sells out, there won’t be anymore. I may get the same style, but it will be a new pattern. Almost every day we get a box of something.”

From geek to boutique
You might say Davis is the “accidental” fashionista—unless, of course, you believe in destiny. When she met her husband Craig Cleveland, Davis was a self-professed computer geek with a degree in computer science from Jacksonville University.

Cleveland was in the furniture business, so the couple decided to open a furniture store in Florida where they were living at the time. While Davis was good with design, her primary role was crunching numbers, because that was what she thought she did best.
When she was in the computer industry, she never felt like she fit in. But she did it because it was easy for her. “My brain is very logical,” she said.

But what also came naturally was her eye for style. “People would come in to see what I was wearing and ask where I got my outfit. Most of the time I got it on Hilton Head, because my parents lived here. So, I got the idea to put clothes in the store,” Davis said.

“There really wasn’t a future in that business where we were. We were furniture, accessories, candles, etc., really eking along. I first brought in handbags and scarves—and they flew out the door.”

In 2010, with the Florida housing market in decline, the couple decided to move to Hilton Head Island. They opened The Pink Pineapple in Main Street Village where they sold furniture and accessories. “My taste was good, but my plan was to be in the back office and let my husband do the sales,” Davis said.

Meanwhile, her wardrobe continued to get noticed. At one point, she swapped out some furniture for clothing, and she immediately saw the greater potential. “I traded someone who was closing a clothing store. This was stuff I didn’t even pick out. It was such a huge difference in how women buy clothing as opposed to how they buy furniture. I had a lady take six months to buy two chairs and six minutes to buy $1,000 worth of clothing. I had an aha, and I said, ‘I think clothing could be the way to go.’ It was gradual, but eventually we got rid of everything except the clothing.”

The Pink Pineapple moved to its current location in South Island Square in 2017. Cleveland now has a successful career as a Realtor with Charter One Realty, while Davis is in her element helping ladies enjoy a happy shopping experience and feel good about themselves.

The couple are proud parents of two teenagers they adopted from Guatemala as infants. “I can’t remember life without them,” Davis said of her children. “They are fabulous.”

Rounding out the family is Hannah, the family dog who is sure to greet you when you visit The Pink Pineapple. And to her good fortune, Davis’ parents and a sister also live in the area.

Davis insists she doesn’t have the aptitude for sales. “Our merchandise is unusual and always changing. We want to have fun, and we want you to have fun when you come here,” she said. “I don’t think I sell. I help you find what you want.” 

The Pink Pineapple is located in South Island Square, 841 William Hilton Pkwy., Suite P on Hilton Head Island. For more information, call (843) 715-0634 or follow on Facebook at The Pink Pineapple of Hilton Head.

  1. Congratulations Sue! So proud of you and your amazing talents. You found your niche. Just wish it was in NY. <3


    — Tammy Davis    Jul 7, 04:09 pm   

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