Caitlyn Warakomski, Founder and Creative Director of HOW DO YOU WEAR THAT, announces the brand’s latest summer drop, Off Duty, a collection of playful yet refined pieces inspired by the breezy spirit of summer on the East Coast.
Each piece is designed to transition seamlessly from beach days to dockside dinners or alfresco evenings at home, embodying the brand’s signature mix of comfort and versatility. The inspiration behind the designs stems from Caitlyn’s own summers spent at her East Coast home, her getaway from the city grind, filled with memories of golden sunsets and impromptu gatherings with friends and family.
The summer drop includes:
- The Brynn Dress in an intricate Atlas Print, a romantic nod to vintage cartography
- The Cotton Essential Set in the Bon Voyage Print, a patchwork of coastal imagery that feels playful yet chic
- The By the Sea Oversized Sweatsuit Set, cozy enough for those sunrise walks, or cool evenings by the seaside
- The Everyday Oversized Tee and Short Set in classic marina stripes, a timeless summer motif (available soon).
How Do You Wear
Crafted with breathable cotton, the entire collection is made to be lived in, whether at the seaside, in the city or for hosting a summer soirée.
“This collection is very personal to me,” says Caitlyn. “It’s inspired by the summers I spend at my home in a quintessential Jersey beach town, a place that always brings me peace, creativity, and joy. Staying true to my brand’s core values, I wanted each piece to feel effortless, but with a little twist.” The Off Duty Collection is available exclusively at howdoyouwearthatshop.com
About HOW DO YOU WEAR THAT
HOW DO YOU WEAR THAT is a fashion brand founded by influencer and entrepreneur Caitlyn Warakomski in 2020, rooted in effortless, playful style with a modern twist. The fabrics are sourced with care, both domestically in the USA, and from selected Italian mills and each print is custom-created and exclusive to the brand. Since the inception, a portion of all proceeds is donated to a rotating selection of charitable organizations, underscoring the brand’s commitment to giving back and making fashion a force for good.
Caitlyn Warakomski is a pioneering influencer and digital entrepreneur based in New York City, known for her authentic approach to fashion. As one of the original “OG” influencers, Caitlyn carved out her own space in the early days of social media, building a loyal and engaged following thanks to her relatable personality and fresh take on fashion.
Caitlyn’s passion for personal style has been a driving force behind her fashion journey, quickly establishing her as a trendsetter known for curating chic, everyday looks, creating ensembles that resonate with thousands. She heartily points out thrifting shopping with her mom as the start of her passion for personal style rather than fashion itself: she would find one-of-a-kind pieces that others overlooked, and remembers a memorable moment when she transformed a printed tablecloth into a dress and skirt that all her friends were eager to buy. Today, she is still driven by style rather than fleeting trends, and enjoys combining pieces that might seem confusing or unexpected in approachable, realistic ways. Her goal is to encourage women to step outside their comfort zones, all while keeping the looks relatable, uniquely blending effortless style and accessible luxury.
Caitlyn’s entrepreneurial journey took off after a career in event marketing. It was only after being in-between jobs in 2015 that Caitlyn found the courage to start blogging. In early 2020, after struggling to find the perfect oversized t-shirt and high-waisted biker short set that was both high-quality and stylish, Caitlyn created a one-of-a-kind piece for herself. Her followers took notice, and asked if she could make some sets available for them to purchase. What started as a personal project unexpectedly turned into a thriving brand. The demand grew, and what was intended to be a charity initiative quickly blossomed into HOW DO YOU WEAR THAT, a brand born out of Caitlyn’s commitment to offering versatile pieces that could be worn every day, for different occasions.
In Caitlyn’s words: ‘Sometimes you don’t want to think about what to wear. HOW DO YOU WEAR THAT offers effortlessly chic pieces to rely on to feel cool, confident and casually luxurious – comfortable enough to wear all day, everyday, yet cool enough to wear out.’
HOW DO YOU WEAR THAT was built on the core belief that fashion should be comfortable, stylish, and empowering. Each collection is carefully designed with an emphasis on high-quality materials and flattering fits. Every piece is cut, dyed, and sewn in NYC, ensuring an eco-friendly production process that supports local industries. Caitlyn also donates a portion of proceeds to charitable organizations like Global Giving and GBM.
Today, Caitlyn is not just an influencer: she’s a respected entrepreneur and leader in the fashion space. She continues to inspire her followers not only with her fashion sense but also as a female entrepreneur, showing them the power of pursuing their passions and building their own businesses.
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