Ryan Winegan is a multi-disciplinary visionary known for her strong work ethic, uplifting energy, positive attitude, and unwavering determination to turn goals into reality. From bold dreams to real achievements, Ryan's life story is shaped by resilience, relentless drive, a clear sense of purpose, and her commitment to making a meaningful impact in people's lives and in the world through her work and influence.

The now U.S. expat was born in Virginia, grew up in the United States, and currently resides in the Veneto Region of Italy. In addition to being a dynamic, award-winning, and creative professional with a wealth of experience across multiple fields — some of which include design, retail, wedding planning, floral design, education, and entrepreneurship — Ryan has achieved many milestones while spending years empowering English language learners, supporting philanthropic endeavours, and steadily working towards her long-term aspirations.

Ryan is a Virginia Polytechnic Institute and State University (Virginia Tech) alumna. The multipotentialite is also a Christian, happily married, and enjoys spending time with family and friends, traveling, doing photography work, singing, songwriting, and staying active through various activities.

Some highlights of Ryan’s achievements have included:

• earning recognition as a U.S. patent-holding inventor;

• successfully achieving a life-long dream of establishing and managing her own creative brand called Winegan Designs® in February 2025;

• having designs from the Winegan Designs brand featured in the Press and on the websites of Vanity Fair, Vogue, and other select publications;

• becoming a certified Life Coach in September 2024;

• planning and executing her multi-cultural Italian-American wedding in Spring 2024, blending diverse traditions into a cohesive celebration and in collaboration with others;

• getting an Italian Secondary School Diploma and a B1 Italian as a Foreign Language certification in Italy;

• dedicating nearly 15 years to teaching English as a foreign language to learners of all age groups in Italy;

• supporting a variety of charitable events and initiatives through active participation and contributions (e.g., Save the Children, charity: water, AIRC - The Italian Foundation for Cancer Research, and others); and

• additional notable accomplishments. Discover Ryan's Work.

During the period of Ryan's graduation from Virginia Tech, she made the pivotal decision to forgo an internship opportunity in the fashion industry in the United Kingdom. Instead, she embraced an unexpected opportunity to work as an Au pair in the charming Italian town of Oderzo for several years. The ancient town, which is situated in the Province of Treviso within the Veneto region, has ancient Paleovenetian origins and was once a prominent Roman municipium.

A special sister city relationship between Suffolk, Virginia and Oderzo — fostered by the historical connection of Italian Amedeo Obici and his Planter's Peanut company — created an opportunity for Ryan to travel to Italy following her university graduation in the spring of 2008. At that time, she was a non-Italian speaker with no comprehension of the language, and she had accepted the proposal to live with an Italian family in a town far from Italy’s major fashion hubs. That experience inspired her to shift her focus from pursuing a career in fashion to immersing herself in the Italian culture and learning how to integrate into it.

Ryan enrolled in Italian language courses and schooling to overcome the language barrier. She had also focused on finding a practical profession she could do in the meantime, which eventually led her to become a certified TEFL/TESOL (Teaching English as a Foreign Language/Teach English to Speakers of Other Languages) teacher and to work teaching English language learners across diverse settings over the years, including preschools, elementary through high schools, public and private institutions, as well as adult education programs. Throughout this journey, she remained steadfast in maintaining a realistic yet optimistic mindset, regardless of the difficulties she encountered, and held on to her childhood aspirations — including her dreams to become a designer, an entrepreneur, and a global philanthropist — even amid life’s diversions.

Though many people advised Ryan to focus her career on English teaching, claiming that she would need to move to another city for job opportunities in the fashion industry and that it would be too tough to break into that industry without the right connections in Italy, she refused to let their doubts, a ‘lack of connections’, and other setbacks she had faced hold her back. As of 2008, and against all odds, Ryan has accomplished many of her lifelong goals, proving that persistence and passion can overcome any challenge.

The Virginian was raised in a military household and spent most of her formative years under the care of her entrepreneurial grandparents, who had owned a floral and wedding planning business in Suffolk, Virginia called Power of Flowers. From childhood through her teenage years, she helped them in their shop with decorating, assisting customers, setting up for events, and other duties. Although the business eventually closed after their retirement, those early hands-on experiences sparked Ryan’s lasting interest in entrepreneurship and the inner workings of running a successful business.

Ryan had also spent part of her formative years participating in 4-H camp activities, dedicating time to community service and volunteering, and working as a sales associate in a department store where she assisted customers, wrapped gifts, and handled diverse tasks.

While growing up, Ryan was often encouraged by her grandparents and family to participate in different activities and live with integrity. They taught her the importance of always remembering her roots — who she is, where she comes from, and how that shapes her present. Today, she remains an active, driven individual who strives to live by these values on a daily basis.

Ryan received elementary, middle and high school education in Suffolk. As a student, the Lakeland High School graduate had participated in different school clubs, including the non-profit student-led Key Club International organization, the non-profit educational youth organization Beta Club, the Foreign Language Club, and others. She also served as the Lt. Governor of Division 21 for the National Key Club and was involved with the Suffolk Sister Cities International organization in Suffolk.

The 2008 graduate of Virginia Tech is also a graduate of the Virginia Tech Corps of Cadets (VTCC) Leader Development Program. She has a Bachelor's of Science Degree in Apparel, Housing, and Resource Management (concentrations in Apparel Design and Merchandising Management), a Business Minor, and a VTCC Leadership Minor. While at university, she was actively involved in several organizations, including the Circle K Club and the Enlightened Gospel Choir, among others. Ryan was also awarded the prestigious Who's Who Among Students in U.S. Universities and Colleges distinction in 2008, an honor given in recognition of exceptional academic achievements, leadership abilities, and a compelling personal essay.