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Ann-Michael McCalister opened Calypso in the Woodland Triangle five years ago this October.
When the fall and spring Keeneland race meets are in session, Ann-Michael McCalister is as much of a meteorologist as she is a boutique clothing shop owner, as she checks the outlook each morning so she has an idea what the next two to three days might offer. The Lexington weather, especially during these times of the year, is as unpredictable as the win, place and show of a two-year-old maiden race, and McCalister wants to make sure her customers are as comfortable as they are fashionable when they come in looking for a new outfit.
McCalister’s store, Calypso, will celebrate its five-year anniversary this October, and she says the small business has established a positive reputation over the years as a place where women and young ladies can come for reliable styling suggestions for any occasion, be it a wedding or a day at the track, though those sort of events initially weren’t McCalister’s forte.
When she opened Calypso in her mid-20s, McCalister’s tastes were more Goodwill than gala. She had tomboy tendencies and wore quirky clothes, not to mention the occasional crimped hair, and she thought her boutique would have a more “rock ‘n roll” sensibility, but she let her customers dictate the shop’s tone, which ultimately became elegant, though eclectic.
“It look me a long time to acclimate to styling someone for a fancy event, especially when I was barely 26 years old and hadn’t attended many formal functions,” McCalister said. “It grew in the direction the clientele took it.”
The store’s inventory may have diverged from what she may have originally wanted to do, but working for somebody else, especially in an uncreative field or job, wasn’t what she wanted to do either.
Graduating with an accounting degree from the University of Kentucky, McCalister took a job in Frankfort working as an auditor, but left the gig after nine months.
“I felt like my personality and flair for life was stifled by a spreadsheet,” she said.
She returned to a field she knew while in college, waitressing, but when an accident left McCalister with a broken ankle, she found herself unable to work and with a whole of time on her hands. She can’t cite the original inspiration or impetus for wanting to open a clothing store, but it was during this time that the idea began to materialize. She took to her crutches and went to scout out a location.
The Woodland Triangle was really the only place she considered, and the first place she looked, having become smitten with the unique neighborhood while she worked as a waitress at Ramsey’s on High Street for nearly five years during and after college. The commercial space on Maxwell Street across the fire station, where Calypso still sits, was unoccupied.
“I wouldn’t own a small business had there not been a space available in this particular area,” McCalister said.
Initially, things were slow in the early days of Calypso – McCalister says sometimes she’d go an entire eight-hour work day without a single customer walking through the door. She filled her time like many bored employees do, tinkering around on the Internet. But she wasn’t waisting her time casually surfing sites, she was slowly building an online presence and audience, first through the by-gone social media site Myspace and then through Facebook, which has become an integral component to her business model as she and her employees take turns posing in the inventory for daily posts.
This past summer McCalister launched a complete, commercially viable website (www.calypsolexington.com) for Calypso that allows customers to look at and order from the store’s available inventory, and considering the amount of time and effort she and her employees have put into the site, she’s very proud of this accomplishment. Given that Calypso only stocks a small quantity of each item to ensure individuality among the Lexington clientele, McCalister thinks the website will become a popular shopping mechanism, but still hopes girls realize that even though they aren’t coming into the store, they can still call and ask for advice or opinions on the items before purchasing. After all, styling suggestions are a mainstay at Calypso.
McCalister credits her supportive network of friends and family for allowing her store to make it the first five years, and she likes thinking about all the possibilities and potential Calypso has in store for the next five.
“If you’re a small business owner, you’re never going to be completely satisfied with where you are,” McCalister said, “so you’re always thinking about what you’re going to do next.”
Calypso Fashion Show
Celebrating 5 years of fashion. 7 p.m. Oct. 7, Tin Roof.