Getting your Trinity Audio player ready...

Ryan Winegan is hoping her journey can inspire others to continue their dreams. 

A Suffolk native who has made her home overseas in Italy, Winegan’s story is one of different routes traveled, but ultimately working out in her favor in both her fashion dreams and her overall life.

“…I just felt that desire to keep looking into fashion and finding ways to be able to get into it,” Winegan said. “Because a lot of people told me that, ‘You know Ryan, you have to live in a very big city.’ Because I live in a small town that’s in the northeastern part of Italy and people were like, ‘No, you have to move to another town. You have to move to Milan.’ … and I was telling myself, ‘I want to prove them wrong!’”

A graduate of Lakeland High School, Winegan says it was a “nice experience” growing up in Suffolk, reflecting on helping her grandparents at a flower shop and participating in extracurricular activities. 

“I enjoyed it a lot,” Winegan said. I had a chance to meet a lot of interesting people, to do different activities—thanks to my grandmother as well—with extracurricular activities at school, and just to really be involved in these a lot of different people…”

After graduating from high school, Winegan went to Virginia Tech, where she graduated in five years as part of VT’s 2008 class. She received her degree in apparel, housing, and resource management with concentrations in apparel design and merchandising management. Along with participating in the Virginia Tech Corps Cadet leadership training program, Winegan also received a business minor. Reflecting on her graduation, she wanted to enlist in the military and follow in her family-oriented family’s footsteps.

“My grandmother [and] my grandfather did the military as well as my mom,” she said. “And so my goal, I was planning to join the military, but after my last year in college, I had to choose pretty much between changing my major with what I wanted to study to do the service or pursuing my dream of wanting to do fashion.”

On what drew her to fashion, Winegan says that she enjoyed drawing in her free time as a child and loved being creative. Originally picking between fashion and architecture when starting college, she felt more drawn to fashion in the end. Two years before her graduation, however, Winegan had an opportunity to visit Oderzo, Italy, in 2006 as part of the Suffolk Sister Cities International Organization.

“So I came with a group of Americans and I had a chance to meet a lot of people and it was a great experience, and I would recommend anyone who can, to be able to come and see the historical connection between both cities,” Winegan said. “And when I went back to the U.S. because I was doing my junior year at the time, I finished my last two years… and during that summer in particular, I was in the process of applying to do an internship in the United Kingdom.”

Visiting Italy again with a friend to celebrate, Winegan says she was contacted by one of her Italian friends who said that a host family was looking for an American au pair: a foreign young person who does domestic work for room and board. Winegan’s response was, “Yes, let’s do it!” This move to Italy took Winegan on an unexpected route in her life, where in order to work and integrate into Italian culture, she shifted her career focus and became a Teaching English as a Foreign Language / Teaching English to speakers of other languages (TEFL/TESOL). Positively noting Italy’s “laidback” culture with friendly people and delicious food, Winegan talked about her “culture shock” and determination to integrate into the country.

“I think something that helped me and that I really had to think about was, ‘What was my long-term goal [that] I wanted to accomplish?’ Because when you’re in a foreign country and before, today we have Google Translator where you have everything at your fingertips, it could be very challenging to be able to interact with people because you can find yourself in situations where people want to talk to you and you want to talk to them, but you have that language barrier,” she said. “And it’s normal to have that fear and sometimes to feel inferior. So, I dealt with that.”

Winegan reflected on her commitment to watching Italian television, reading books explaining English and Italian languages, and working hard to learn.

“…I just made myself practice and try to be around people even if I didn’t understand them and remind myself that, even though I’m here, I want to be here because I want to meet people,” she said. “I want to be able to use this experience as well to help me if I go back to the States because you just never know for the future, and make the best out of it.”

Despite the change in her path, Winegan did not put an end to her fashion dreams. After the COVID-19 pandemic, Winegan says she wanted to look back into fashion and to continue her passion. Collaborating with an Italian company called AliveShoes, which she notes she discovered “by accident,” Winegan came up with her own concept and designed her first shoe and accessory collection.

“And what they do is they collaborate with designers, creators, and people who just like to express their creativity, and they let their designers create shoes, you can design the type of styles that you want to use the type of material,” she said. “I personally like them because they’re Italian-made products and they’re made up of authentic Italian leather, suede, and other materials.”

Following her first design of Bow Ballerina Flats, Winegan has also created Zip Military Boots, classic High Heels, and a Designer Luxury Elegant-Fashion Bag. After getting positive feedback, she has decided to stick with it and is gradually building her collection.

“… Right now, I’m working on creating my different collections so that I am able to present something for people to decide because, with my first design with the leopard print, I decided to go with that because I love leopard,” she said. “But now my new collection is black and white and it’s something that’s more ‘classic’ that can be used in other occasions.”

While she still serves as a teacher and is planning for her upcoming multicultural wedding in May, Winegan says she wants to become an entrepreneur and work more in designing while incorporating the skills she learned as a teacher. She further emphasized not wanting to be limited to “one specific field,” expressing wanting to do more with photography, traveling, social media, and much more. Likewise, Winegan gave some advice for those just beginning their young adult lives and going off to college studies.

“Have an idea for what you want to do for a long term goal, but be open to alternative possibilities,” she said. “Because for me when I graduated, I expected to get right into the fashion industry and get started right away, but it didn’t happen. And sometimes life, I think, will take us in different directions as a way to help train us and to help prepare us for the things that we want to do.”

Winegan expresses learning from every experience, noting that sometimes, one might have to accept jobs they normally would not want to do.

“For example, when I started teaching, I did not want to be a teacher! When I graduated and came to Italy, I was like ‘I’m never going to be a teacher!’ and then I turned out to be a teacher. But whatever you do, do it with excellence and learn from it,” Winegan said. “Sometimes you might have to be humble. Whether it’s picking up or cleaning or being someone who works to pick up trash, whatever it is, learn to be humble and look at every experience as an opportunity.”