One of the company’s fashion shows ended on the streets of New York. Credit: Baba Khid

When Lolita Malone was growing up with three younger sisters and their baby brother in rural Jamaica, she and her siblings shared clothes, shoes, and pretty much everything. They had a tiny allowance but big fashion dreams, so they would hit up thrift shops and cut and upcycle clothes.

“We were making things beautiful that weren’t originally beautiful,” Lolita says. “We had to find our inner ‘fly girls’ when it came to fashion.”

The idea of “fly girls” was born in this sisterhood decades before Lolita Malone and her daughter, Maui Malone, gave it a name in their Manhattan-based fashion brand, Maui x Lolita. “Bold, daring women who not only take fashion risks, but are comfortable with how they look and how they dress, and they don’t want to look like anyone else,” says Lolita of the label’s identity.

The older Malone developed a penchant for fashion due to her need to create clothes by combining different pieces, a sort of “frankenstyling.” Her talent would ultimately take her designs to the walkways of some of the world’s biggest fashion shows. Last month, she showed her fall/winter collection during New York Fashion Week. The theme, “modern rebellion,” featured bold styles meant for the workplace, like hyper-flared pants, atypical cuts and the use of grommets.  

How a practical need fueled the launch of this mother-daughter fashion design company — and how their creativity keeps it growing.

How Malone designed her first “fly girl” creations

When Lolita’s family migrated to Maryland in 1991, her early passion for creative design continued. However, in high school, she struggled to find a prom dress that fit her petite frame. “I was like two twigs and I had no choice but to create things for myself or I would never look good,” she said. 

She enlisted the help of a local dressmaker to bring her design to life: a one-shoulder strapless dress with a side cutout at the stomach and a long leg slit. It was inspired by Hollywood star Heather Locklear’s 1996 Golden Globes dress. But Lolita’s had straps going across the sides. 

By the time her second prom rolled around, she had taught herself how to make her own designs from scratch. And the dressmaking continued well after graduating from high school at age 16. While studying fashion merchandising at Morgan State University in Baltimore, Lolita started making miniskirts and cropped tops for herself and friends to wear to clubs. 

“It just ballooned from there,” she said.  

Maui X Lolita’s “Modern Rebellion” fashion show featured bold workwear for the “fly girl.” Credit: Laurianne Ogay.

How Maui X Lolita found a home in NYC

Lolita wasn’t the first in her family to work in the fashion industry: her aunt attended the Fashion Institute of Technology. When Lolita’s family visited her in New York City, the young woman found loads of inspiration. 

“One of the bedrooms in her house was this huge room, and there was just fabric everywhere,” Lolita said. “It was just colorful and beautiful, and I was in heaven.”

Her aunt couldn’t help but notice Lolita’s awe over her creative spaces. She helped her niece as best as she could while they lived in different cities, giving her guidance and encouragement over the phone.

Back home in Maryland, and later in Florida, Lolita would practice by heading to stores and letting fabrics speak to her, she says. She played around with different techniques and materials until she found her niche in swimwear. “I was so tiny I had no choice but to make my own bikinis,” she said. 

To the bafflement of nearly every other designer she came across, she enjoyed making swimsuits. For most, the material moved around too much to handle. 

This zest for design continued when she and her husband moved to the Orlando area. There, Lolita pursued fashion as a one-woman business. But repeated business trips to New York City over the years inspired her to eventually move to the Big Apple soon after the launch of Maui X Lolita. 

“Before [Maui X Lolita], I did primarily swimwear,” Lolita said. “But it just didn’t take off like I wanted it to. I always said that Maui was the missing piece of the success puzzle for us.”

The birth of Maui x Lolita

Lolita’s and Maui’s company launched during the pandemic. While the family was stuck at home during the lockdown, Lolita began making “quarantine couture.” Apart from the usual swimsuits she sold, she was sewing clothes for herself. One was a floral tracksuit that her daughter Maui insisted she sell. 

Lolita did one better: she decided to start a company, and invited her number-one fan to join her. They did everything by the book, including a business plan and contract. Maui was studying finance at Loyola Marymount University, a degree that included business classes. She created their website, and her mother made the clothes. They had no money to hire anyone, so they did everything themselves: modeling, photographing, editing photos, and packaging. 

In the frenzy of the pandemic-era spike in online apparel sales, Lolita was sewing in her bedroom day and night to make orders that shipped as far as Australia. After the lockdown was lifted, her daughter headed back to school in Los Angeles and demand began winding down. 

Lolita knew it was time to move her business to New York City. She was already going back and forth between New York and Florida. So she and her husband packed up and moved to Manhattan, where Lolita officially launched the company. She found a cheap place on East 34th Street through Craigslist, where she worked surrounded by boxes.

“I couldn’t even breathe and I was stuck in that tiny room,” Lolita says. “I was just stressed out. I wasn’t showering, I wasn’t eating, I wasn’t sleeping. I was there for like 20 hours a day, sometimes 24 hours.”

She eventually talked the landlord into giving her extra space. As the business grew, she was eventually able to hire help. 

A Maui X Lolita fashion show that ended on the streets of Manhattan. Credit: Baba Khid

The ‘fly girls’ and ‘fly guys’ of Maui X Lolita

Most of the few staffers at Maui X Lolita are also Jamaican immigrants: Yannik Taylor, the company’s director of operators and brand manager, and Kyrie Thompson, its stylist. Working with the company has also fueled the rediscovery of their own ‘fly’ selves. 

Before Maui X Lolita, Taylor had a more secure healthcare job with benefits: “I never thought I would ever get into fashion,” he said. “Healthcare is dependable, but I never felt fulfilled.” 

Thompson, who used to work as a truck driver, had never imagined becoming a stylist.  

“I was super miserable because I didn’t have time for me,” he said. “And the one day that I had to be myself, I’d always go shopping and try to dress up and go outside because that’s what I love to do — I love clothes.” 

His friends started calling him a model. He started seeing new possibilities in himself. He set up a small photo shoot and started promoting himself, amassing thousands of social media followers.  

When he met Lolita at a fashion event, she took a chance with him in a major fashion show. “I’m just super grateful for Lolita,” he said. “After the last show I did, we went out to eat and I just started crying.” 

Thompson has since worked to cast and style models for every major Maui X Lolita project. 

Maui, whose literal and artistic voice graces the company’s fashion shows and videos, has had her own experience in finding what works for her own “fly” self. At 4 feet 11 inches and thin, she struggles finding clothes that fit, much like her mother.

“That’s something that we embrace — being able to cater to the people that are looked over when it comes to dressing and size inclusivity, on the opposite end,” Lolita said. “There’s a lot of focus on the larger end but there’s very, very little focus on the skinnier people or tiny shorter people.”

Maui’s height made her mainstream modeling aspirations impossible, Lolita said. But in their company, Maui often models, not just for the website but also fashion shows — sometimes alongside her mother. Lolita says they get along so well in part because their skills complement each other. And they both share a zeal to create. 

“I had nothing, and I dreamt of big, beautiful, fabulous things,” Lolita says of her younger “fly girl” self. “Having nothing and being forced to work with the little things, has given me the advantage over people with all the money in the world, with zero creativity.”

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