Caitlyn Warakomski on Personal Style, Modern Luxury, and Dressing for Real Life Ahead of New York Fashion Week
As New York Fashion Week approaches, the fashion conversation naturally turns toward creativity, craftsmanship, and the ideas that set the tone for the season ahead. Runways become a place where design meets storytelling, offering both inspiration and aspiration. For Caitlyn Warakomski, founder of HOW DO YOU WEAR THAT, fashion has always been about carrying that inspiration beyond the runway, focusing on pieces that continue to feel relevant long after the shows wrap.
Based in New York City, Warakomski built her career by trusting personal style over constant reinvention. Long before launching her brand, she cultivated a following drawn to her ability to make unexpected pieces feel intuitive, wearable, and honest. That same philosophy now anchors HOW DO YOU WEAR THAT, a label rooted in comfort, thoughtful production, and clothing designed to move through everyday life with ease.
As the fashion calendar turns toward NYFW, Warakomski reflects on her journey from event marketing to entrepreneurship, her commitment to domestic production, and how modern luxury continues to evolve for women who want clothes that work beyond the runway.
An Eye for Experience Before Fashion
Before launching HOW DO YOU WEAR THAT, Warakomski spent years working in event marketing, a background that continues to inform how she approaches fashion today.
You started in event marketing before building HOW DO YOU WEAR THAT. What lessons from that chapter still guide how you run your business today?
Working in event marketing really shaped how I think about experience. You become very aware of how people move through a space, how something feels, and where the small details matter. Today, I approach HOW DO YOU WEAR THAT in a similar way, thinking about the full experience around the brand, not just the product itself.
Why Personal Style Outlasts Trends
In an industry driven by seasonal cycles, Warakomski has remained deliberate about not chasing what is new simply for the sake of it.
Your focus has always been personal style over trends. How has that mindset helped you build longevity in a fast-moving industry?
Yes! I love personal style so much. That’s true, and it’s because trends move so fast, and if you chase every single one, you’ll actually end up losing yourself quickly. Focusing on personal style has allowed me to stay grounded and consistent. I’m not aiming to reinvent myself every season and I think this sense of honesty is what resonates with my community the most. I just make what I actually want to wear and crave in my closet and what I feel the most comfortable in, sometimes it can be more trend forward, but oftentimes it’s just me.
When a Personal Project Became a Brand
HOW DO YOU WEAR THAT began without a formal business plan or launch strategy. Instead, it evolved organically through community demand.
HOW DO YOU WEAR THAT began as something you made for yourself. When did it click that this was becoming a real business?
I didn’t have that big ‘ah-ah’ moment, but I started noticing how naturally the pieces were fitting into our customers’ lives, and when people kept asking for the same pieces again and again, that’s when it really clicked. It stopped feeling like something I was just experimenting with for myself and more like a responsibility to build something lasting for the community I built and that has genuinely shown me they trust me over the years.
New York Fashion Week Through a Real-Life Lens
As NYFW approaches, Warakomski looks to the runway not for fantasy, but for ideas that translate beyond the venue.
With New York Fashion Week coming up, what are you hoping to see more of on the runway, especially when it comes to everyday dressing?
I can’t wait to attend NYFW again, it’s a special time for anyone working in fashion. I love seeing clothes that move well, feel chic but comfortable, and translate naturally into real life. Granted, fashion is art, but you can truly see when designers think about how women actually live in their clothes, not just how they photograph.
You’re known for styling unexpected pieces in approachable ways. Are there silhouettes or styling ideas you think will stand out this NYFW season?
I think relaxed tailoring will continue to stand out and I also love seeing contrasts, something oversized with something more fitted, or a polished piece worn very casually. Those combinations feel modern and realistic, and they give people permission to make the look their own.
Why Domestic Production Still Matters
In an era where speed often dictates production, HOW DO YOU WEAR THAT remains committed to keeping its process close to home.
The pieces are cut and sewn in the United States. Why is that commitment still essential as fashion evolves?
It’s not always possible but we have chosen our factories to be as close to us in an effort to never lose sight of quality, whilst keeping production thoughtful and intentional. This allows me to be there in person making the very last amends or touches to any design, and it’s something that I’ve really cherished so far. Everything we have ever made thus far has been made here in NY.
Defining Modern, Accessible Luxury
As HOW DO YOU WEAR THAT continues to grow, Warakomski remains focused on maintaining alignment between growth and intention.
Looking ahead, how do you see your role growing as a founder and business leader in modern, accessible luxury?
I want to continue building something that feels honest, thoughtful, and lasting, by leading with integrity, staying closely connected to our community, and listening to how they actually live in the clothes. And don’t get me wrong: growth is exciting, but only when it feels intentional and aligned. For me, modern luxury is about ease and confidence by wearing pieces that fit seamlessly into everyday life and feel just as right five years from now as they do today.
In a city that thrives on reinvention, HOW DO YOU WEAR THAT continues to prove that staying grounded can be the most forward-looking choice of all.
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