Her Story
About Diana
Diana Ross Perry, MFA, is a fashion merchandising, buying, and marketing professional with more than 20 years of experience spanning fashion merchandising, product development, retail, styling, marketing, and brand development. She currently serves as a Fashion Buyer through Diana Style House (DSH) while actively pursuing new opportunities in fashion buying, merchandising, styling, and visual merchandising. Her professional background includes roles as an Assistant Buyer, Assistant Merchant, Global Sourcing/Sourcing Assistant, E-Commerce Merchandising Coordinator, and Junior Client Advisor, providing her with experience across product assortments, vendor relationships, forecasting, sourcing, retail strategy, and customer experience. Her entrepreneurial work through DSH includes wardrobe styling and signature apparel collections, while DSH Creative extends her expertise into contract-based merchandising and marketing services.
Perry earned a Bachelor of Arts in Marketing from Penn State University and a Master of Fine Arts in Fashion Merchandising & Retail Management from LIM College. She has continued to expand her professional knowledge through training in sales forecasting, hotel negotiation, and destination strategy and sales. Her experience includes working with IT'SUGAR, Chico's FAS, FlexShopper, and LXRandCo, alongside her entrepreneurial work through DSH. She combines analytical and creative capabilities, with expertise in merchandise planning, buying, product development, inventory forecasting, marketing, styling, and brand strategy. She has also contributed to Paige Magazine and maintains a strong interest in building a career that integrates fashion, commerce, creativity, and entrepreneurship.
Perry's professional philosophy is shaped by her Jamaican upbringing, strong work ethic, faith, determination, and commitment to building a lasting legacy for her four children. She attributes her resilience to remaining focused on her vision and continuing forward despite professional setbacks or uncertainty. She believes in leading with love, emphasizing empathy, authenticity, perseverance, and meaningful relationships in both her personal and professional life. Her commitment to giving back is reflected in the DSC Initiative in Jamaica, which she founded in 2023 to provide mentorship and educational support for children. As she continues developing DSH and DSH Creative while pursuing opportunities within the fashion industry, Perry's long-term vision is to become a leading merchant and buyer while creating a business legacy that combines fashion, entrepreneurship, community impact, and service.
Her Interview
Ten minutes with Diana
01What do you attribute your success to?
I attribute my progress and resilience to my Jamaican upbringing, strong work ethic, faith, determination, and the motivation I receive from my four children. My upbringing taught me to work hard, remain persistent, and keep moving forward. While others may look at my education, family, and business accomplishments and consider me successful, I believe I am still working toward my full potential. I remain focused on making progress every day, continuing to develop myself, and building something meaningful for my children and future generations.
02What’s the best career advice you’ve ever received?
I attribute my progress and resilience to my Jamaican upbringing, strong work ethic, faith, determination, and the motivation I receive from my four children. My upbringing taught me to work hard, remain persistent, and keep moving forward. While others may look at my education, family, and business accomplishments and consider me successful, I believe I am still working toward my full potential. I remain focused on making progress every day, continuing to develop myself, and building something meaningful for my children and future generations.
03What advice would you give to young women entering your industry?
I would encourage young women entering fashion, merchandising, and buying to stay focused, believe in themselves, and never give up when challenges arise. These industries are highly competitive, and there are many talented and highly skilled professionals pursuing opportunities. However, each person has unique qualities and experiences that can help them stand out. Believe in your vision, continue developing your skills, maintain your faith, and keep moving forward even when circumstances do not go according to plan. Your individuality can become one of your greatest professional strengths.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in fashion, merchandising, and buying is the highly competitive nature of the industry. There are many talented and highly skilled professionals competing for opportunities, which makes it important to continually differentiate yourself. At the same time, I see that competition as an opportunity to stand out through my unique perspective, personal presentation, entrepreneurial mindset, and ability to bring together merchandising, marketing, styling, and brand development.
My entrepreneurial work also creates opportunities beyond traditional employment. Through DSH Creative, I can provide contract-based merchandising and marketing services to businesses, while DSH allows me to continue developing my signature apparel collections and wardrobe styling services. I see the combination of traditional industry expertise and entrepreneurship as an opportunity to build something distinctive and meaningful.
05What values are most important to you in your work and personal life?
Leading with love is my guiding value. To me, love encompasses empathy, sympathy, understanding, and the qualities that allow us to build meaningful relationships with others. Faith, perseverance, authenticity, and a strong work ethic are also central to how I approach both life and business. I am motivated by creating a positive legacy for my children and contributing to my community, and I believe that success is most meaningful when it is accompanied by purpose, authenticity, and a willingness to give back.
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