The blue-collar lessons that Jenny Swank Krasteva learned in tiny Valier have fueled her rapid rise to an executive position at one of the world’s most influential fashion houses

Story by Myers Reece | Photography by Mandy Mohler
In high school, Jenny Swank preferred hammering nails on construction sites over sitting in an office, but neither of those jobs satisfied her creative appetite. So the question nagged: How was a girl from Valier, population 500, supposed to channel these artistic ambitions bubbling up inside her?

Swank’s answer came in the form of Kevin Hayes, an older boy at her school who had left their tiny Montana farming community to study fashion in Los Angeles. She arranged to visit Hayes and immediately knew she had found her calling.

“I thought, ‘This is so cool,’” Swank, who is now Jenny Swank Krasteva, said recently in an interview from her home in Germany. “Kevin took me under his wing and said, ‘It’s possible. You just have to work hard.’”

“Most people in this industry were born into it, or knew somebody, or had money,” she added. “But for a small-town girl, it’s different.”

Rather than a deterrent, she saw a challenge that both her personality and childhood spent working for family-owned Swank Enterprises had equipped her to overcome.

“Growing up in the construction business, I was always interested in business and hard work, and all the things you had to go through to get where you wanted to be,” she said. “But coming from such a small town, you dream of something bigger.”

Swank Krasteva’s willingness to dream big and work hard have carried her rapidly through the ranks of fashion design and landed the Montana native in her current executive position as senior head of creative at Hugo Woman, a branch of Germany-based Hugo Boss, one of the most influential apparel manufacturers in the world with a net worth of nearly $3 billion and stores in 110 countries.

As Swank Krasteva has embarked on a flourishing fashion career in distant locales such as New York and Germany, back home, Swank Enterprises has cemented its status as one of Montana’s most prominent construction firms. With more than 200 employees, the company regularly secures contracts to build hospitals and other large projects across the state. While Swank is still headquartered in Valier, it has offices in Billings and Kalispell. Her father, Derek, and uncle, Dewey, who lives in the Flathead, are both executive vice presidents. Her grandfather, Dean, founded the company in 1960.

Both of Swank Krasteva’s older siblings, Jeff Swank and Jacquie Foster, also work for the family business. Foster, an accountant, said her younger sister was never one to settle. She was a record-breaking state champion swimmer, a standout on the basketball and volleyball teams, and an eager summer construction laborer after office work failed to stimulate her.

“If Jenny decided she was going to be a fashion designer, she was going to be the best,” Foster said. “She can’t settle for just doing something. She has to be the best.”

"Hugo is the girl who’s sneaking out the window," Swank Krasteva said.

“Hugo is the girl who’s sneaking out the window,” Swank Krasteva said.

When Swank Krasteva showed up as a bright-eyed 18-year-old for her first day of fashion design courses at the Academy of Art University in San Francisco, she was already behind her peers, many of whom had taken classes in high school through college art programs such as Parsons School of Design. Furthermore, most of her classmates hailed from metropolitan areas with thriving fashion scenes: Tokyo, Los Angeles, New York, not Valier.

So she buckled down, committed herself to learning at a speedy clip, and steadily closed the gap while classmates who had started far ahead of her were weeded out by the grueling curriculum. She had 900 freshmen in her class; by the time she graduated, there were 60 left.

“It was a huge elimination process,” she said.

Having survived that formidable educational gauntlet, she immediately confronted the more imposing professional version after she was awarded an internship with fashion designer Zac Posen in New York City upon graduation. Posen was a rising star in the industry with financial backing from then-named Puff Daddy. She opted for the Posen gig over a job offer from Abercrombie & Fitch.

“Zac said, ‘You’re not going to be designing T-shirts for the rest of your life,’” Swank Krasteva said.

After she completed the internship, Posen created a position for her, giving Swank Krasteva her first real job in fashion design. She regularly worked 14-hour days, seven days a week. But the demanding schedule only elevated her professional energy.

“I was in New York City, 22 years old, living the dream,” she said, adding that her year-and-a-half with Posen was a “fashion boot camp” in which she became a jack of all trades. That set her up well for her next position at Carolina Herrera, which she called “another dream job.”

At Carolina Herrera, Swank Krasteva was a design assistant, giving her a role in the actual design process, an opportunity she had long coveted. Her mentor there, Hervé Pierre, made fashion headlines earlier this year after designing the First Lady’s inauguration gown, including a New York Times profile headlined “The Man Who Dressed Melania Trump for the Ball.”

“Hervé was an amazing mentor for me, not just for designing but also building a line — a collection that buyers want to buy the whole thing,” she said. “He was so kind, a breath of fresh air in an industry where there are so many mean people.”

After a while, the ever-ambitious Swank Krasteva outgrew her position at Carolina Herrera and went to work for Posen again. This time, she was in charge of a label, the one calling the shots, still young and relatively early in her career.

Then came the call from a headhunter who had bumped into her LinkedIn profile. The woman on the line had a thick German accent, but Swank Krasteva could make out one word clearly: Hugo.

“You mean Hugo as in Hugo Boss, as in the huge international Hugo Boss?” she recalls thinking.

The family floating down the River Jenny.

The family floating down the River Jenny.

That phone call set in motion a process that would land Swank Krasteva in Germany in October 2015, along with her husband, Milen Krastev, who also works in fashion, and their 6-month-old baby. In Milen’s native Bulgaria, last names are distinguished between masculine and feminine, hence Krastev and Krasteva.

“It was the ultimate dream job, but it was a big, crazy decision,” she said. “We had to move to Germany at the drop of a hat. Our baby was still young enough, so it was now or never.”

“My husband always laughs and says, ‘We’re floating down the River Jenny, wherever it takes us,’” she added. “I believe you just have to keep creating opportunities for yourself — say yes to that phone call.”

The family settled in Riederich on the outskirts of Metzingen, a small town near Stuttgart where Hugo Boss headquarters are located. Neither Milen nor Jenny speaks German, but the ubiquity of English speakers at the company softened the culture shock, as did the fact that Metzingen isn’t too much bigger than Valier. Even after decades of expansion, with stores, factories and offices in countries across the world, the luxury fashion house remains based out of the little town of its 1924 origins.

Swank Krasteva works for the Hugo side of the business, heading up the creative department at Hugo Woman. Under her watch are teams for design, marketing and branding, who band together, along with collaborators such as stylists and photographers, “to use clothing to tell stories.” The stories begin in Swank Krasteva’s head and then grow from her vision. It is indeed art, a fully formed realization of the creative impulses that have guided and motivated her since childhood.

“Hugo is the younger, cooler little sister to Boss,” she said. “Boss is the older sister who does everything right, Hugo is the girl who’s sneaking out the window. It has a higher fashion grade. It takes a few more risks. It’s more trend oriented.”

Swank Krasteva has made friends from a nearby U.S. military base, including one from Whitefish whose father worked for Swank Enterprises. It’s a comforting connection to her roots, a reminder of the Montana grit that pushed her to a high-level position at a global powerhouse at age 31.

“Montana makes you tough; it makes you hard,” she said. “Nobody’s going to be there to hold your hand when your tire blows. That’s Montana.”

She hopes she can be an example of what happens when Montana toughness converges with bold aspirations.

“Hopefully there are other little girls in Montana who dream of something bigger and see that’s it possible,” she said. “You don’t have to stay in a small town forever.”