Top Fashion Influencer: Caitlyn Warakomski
Top Fashion Influencer Credits: Courtesy of Caitlyn Warakomski Caitlyn Warakomski, the New Jersey–based influencer who moves seamlessly between New York’s energy and suburban ease, is one of the original voices in the digital fashion space. With over 693K followers on Instagram and 255K on TikTok, she has long established herself as a trusted source of inspiration for women looking to explore their personal style in a way that feels both empowering and approachable. View this post on Instagram A post shared by HOW DO YOU WEAR THAT™ (@caitlynwarakomski) Caitlyn’s style is ever-evolving—feminine, relaxed, polished, and a little playful all at once. She doesn’t shy away from experimenting with colors, shapes, and prints, effortlessly shifting from a denim-on-denim look, to a maxi white skirt paired with a beige jacket and bag, to a boho-inspired outfit complete with flip flops and chunky jewelry. One day she’s in sporty chic mode, the next she’s in a flowing, feminine silhouette. But no matter the vibe, the through line is clear: her looks always feel wearable, intentional, and grounded in authentic style rather than passing trends. Her brand, How Do You Wear That, mirrors this exact ethos. Born from her personal passion for individual style, it focuses on classic silhouettes with a modern, slightly funky twist. Each piece is made from high-quality materials, cut, dyed, and sewn in New York City to support local production and maintain an eco-conscious approach. The brand’s mission is rooted in creating clothes that are comfortable, stylish, and confidence-boosting, making it easy for women to experiment with fashion without feeling out of place. Caitlyn also makes sure her platform gives back—donating a portion of the brand’s proceeds to organizations like Global Giving and GBM, combining purpose with passion. View this post on Instagram A post shared by HOW DO YOU WEAR THAT™ (@caitlynwarakomski) Her entry into fashion didn’t come through magazines or trend cycles, but through the magic of thrifting with her mom, where she discovered the joy of finding overlooked gems and styling them in new ways. She still recalls the time she turned a printed tablecloth into a dress and skirt that her friends all wanted to buy—a clear sign that her love for unique styling was always there. That early foundation continues to shape her content today. On both Instagram and TikTok, Caitlyn champions the idea that style should feel personal, imperfect, and fun. She’s known for mixing pieces that might seem like they shouldn’t work together—and then making them look totally effortless. Whether she’s styling a statement piece or sharing a simple everyday outfit, Caitlyn champions the idea that style should feel personal and imperfect in the best way. Her influence continues to grow not just because of what she wears, but because of how she invites others to wear what they love—with confidence, curiosity, and creativity.
Caitlyn Warakomski, the New Jersey–based influencer who moves seamlessly between New York’s energy and suburban ease, is one of the original voices in the digital fashion space. With over 693K followers on Instagram and 255K on TikTok, she has long established herself as a trusted source of inspiration for women looking to explore their personal style in a way that feels both empowering and approachable.
Caitlyn’s style is ever-evolving—feminine, relaxed, polished, and a little playful all at once. She doesn’t shy away from experimenting with colors, shapes, and prints, effortlessly shifting from a denim-on-denim look, to a maxi white skirt paired with a beige jacket and bag, to a boho-inspired outfit complete with flip flops and chunky jewelry. One day she’s in sporty chic mode, the next she’s in a flowing, feminine silhouette. But no matter the vibe, the through line is clear: her looks always feel wearable, intentional, and grounded in authentic style rather than passing trends.
Her brand, How Do You Wear That, mirrors this exact ethos. Born from her personal passion for individual style, it focuses on classic silhouettes with a modern, slightly funky twist. Each piece is made from high-quality materials, cut, dyed, and sewn in New York City to support local production and maintain an eco-conscious approach. The brand’s mission is rooted in creating clothes that are comfortable, stylish, and confidence-boosting, making it easy for women to experiment with fashion without feeling out of place. Caitlyn also makes sure her platform gives back—donating a portion of the brand’s proceeds to organizations like Global Giving and GBM, combining purpose with passion.
Her entry into fashion didn’t come through magazines or trend cycles, but through the magic of thrifting with her mom, where she discovered the joy of finding overlooked gems and styling them in new ways. She still recalls the time she turned a printed tablecloth into a dress and skirt that her friends all wanted to buy—a clear sign that her love for unique styling was always there. That early foundation continues to shape her content today. On both Instagram and TikTok, Caitlyn champions the idea that style should feel personal, imperfect, and fun.
She’s known for mixing pieces that might seem like they shouldn’t work together—and then making them look totally effortless. Whether she’s styling a statement piece or sharing a simple everyday outfit, Caitlyn champions the idea that style should feel personal and imperfect in the best way. Her influence continues to grow not just because of what she wears, but because of how she invites others to wear what they love—with confidence, curiosity, and creativity.
