With her penchant for menswear-inspired clothing and tailored pieces, Regina Shepherd ’09 has a distinct sense of style. She mixes several different looks to create a style that is unmistakably her own. Her trademark skinny jeans and tailored button-ups are commonplace, but Shepherd has the ability to take basic pieces and personalize them. She uses a simple yet genius method of layering, starting from one or two basics. She then builds up the outfit with several other items to create a fresh and new look. Yet with such great attention to detail, Shepherd’s main objective is simply to be comfortable. “If I don’t feel comfortable in what I’m wearing then I just don’t feel good, and to me that’s the aim when I get dressed in the morning,” she said. In a few words, Shepherd’s style is “weird, comfy, simple and fun.” Her only mandate about clothing is that a person should love wearing what they wear. “I can tell you that what you wear should boost how you feel about yourself. How you feel about yourself when you step out of your dorm, whether it be in rain boots and boxers or a pea coat with nothing under it, you should feel secure and happy with how you look. That’s what’s important,” Shepherd said. Prior to coming to Phillips Academy, Shepherd never really had a style of her own. According to Shepherd, “Before I came to Andover, what I wore depended on my mom’s taste and the latest style or trend that was in.” As most would agree, both styling tips from your parents and following fashion trends can easily end up in disaster, or at the very least, present you look like someone you’re not. Shepherd is the type of person who wears her clothes and doesn’t let her clothes wear her. People often wear outfits that just don’t look authentic on them; their lack of comfort and confidence shows on the outside. Shepherd embodies the idea that one can be comfortable and fashionable at once. Her secret is that she doesn’t put too much effort into finding the perfect outfit. “When I came here, I realized that no one really cared whether you were dressed up or wore boxers to class,” she said. “And so I decided to put less and less effort into what I wore as the years progressed. I decided what you wore wasn’t as important as how you wore it.” Shepherd’s inspiration comes from her surroundings—the diversity she sees around her encourages her to think outside the box with her clothing. Shepherd said, “My style icons are everyone I see on a day to day basis. Everyone has something unique to bring to the table, whether it’s by how they put their clothes together or their body shape.” She continued, “In seeing how everyone is different but the same; I remember to dress for myself in that same way.” Whether it is from her mother or from people walking around on campus or in New York, Shepherd takes bits and pieces of everyone else’s ideas and somehow manages to throw them together and come up with something original.