Caitlyn Warakomski is a pioneering influencer and digital entrepreneur based in New York City, known for her authentic approach to style and her ability to make fashion feel both attainable and inspiring. As one of the original creators on social media, she built a loyal and engaged community during the early days of the digital landscape, long before influencing became a mainstream career.
We sat down with Caitlyn to discover more about her career to date as well as her journey as the founder of fashion brand, HOW DO YOU WEAR THAT™
Can You Tell Us How Your Passion for Personal Style First Began?
Absolutely. My love for personal style really started when I was little. My mom and I would go thrifting together all the time, and I loved finding pieces that everyone else skipped over. I remember taking a printed tablecloth and turning it into a dress and a skirt, and suddenly all my friends wanted one. That moment showed me that style could be imaginative and fun, and that you do not need “fashion” to make something feel special!
You’ve Said Your Love Was Always for Personal Style Rather Than the Fashion Industry Itself. How Does That Shape the Way You Dress Today?
I have always been more driven by how clothes make you feel than by chasing trends. I love mixing pieces that might seem unexpected or confusing at first, but somehow make sense once they are on. I want style to feel approachable and realistic, not intimidating. I want women to think, “Oh, I can do that too,” and to try pieces they might not normally reach for!
What Inspired You To Finally Launch HOW DO YOU WEAR THAT™ as a Blog in 2015?
I have wanted to do it for a couple years before actually starting it, but I was shy, and the idea of taking photos of myself and posting them online felt overwhelming and…WEIRD! But ultimately, I really wanted to share what a lot of my friends would come to me for – “how do you wear this..or how should I wear that…etc” and share my love for styling and clothes.
In 2015 I was between jobs, and I finally had that quiet moment where I thought, well I guess now is the time to start that blog thing I have been dreaming up!
As Someone Who Started as an OG Creator, What Has Helped You Stay Relevant in Such a Fast Changing Industry?
Staying true to my style and being consistent. The industry moves quickly, and there is always pressure to reinvent yourself, but I think people connect with authenticity. I try to evolve without losing the core of who I am, and I think my audience appreciates that. Thank you for thinking I am relevant haha! It is always evolving. But I think it’s really about staying true to my style and being consistent. The industry moves so quickly, and there is always pressure to reinvent yourself, but I think people connect with “authenticity” — I know that word is thrown around so much, but I try to evolve without losing the core of who I am, and I think (well, hope!) My audience appreciates that.
And then, in 2020, you launched your own brand, HOW DO YOU WEAR THAT™.
Your First HDYWT Product, the Oversized Tee and Biker Short Set, Became an Instant Hit. How Did That Idea Come About?
It sort of happened by accident to be honest. It began because I simply could not find the set I was craving in my own wardrobe. I wanted something high-quality, roomy, cool and flattering, and nothing out there felt right. So I made one for myself. I went on IG stories to talk about something unrelated to what I was wearing, and people immediately asked where they could buy it. I produced some sets to raise money for charity, and they sold out right away. That moment changed everything. From there, we have grown organically and expanded into different categories over the years – it has been a dream!
What core belief guides HOW DO YOU WEAR THAT™ as a brand?
That fashion should feel comfortable and empowering. I want women to feel cool, confident and casually luxurious in pieces they can reach for over and over again. No overthinking, no stress. Something that is really important to us is local production, in order to support the NYC Garment District, which allows me to visit the factories regularly, touch with my own hands and never compromise on quality.
Your Pieces Frequently Sell Out. Why Do You Think the Brand Resonates So Strongly With Your Audience?
My audience has been with me for years, and they know I would only create pieces I truly wear. The designs are versatile and thoughtful, nothing gimmicky. I think women appreciate pieces that feel real and wearable, not so trend driven or disposable, but still modern with a unique flare.
How Does Being a Founder Influence the Way You Now Create Content?
Oooh! I love this question. I think I am more intentional now. Content is not just an outfit anymore, it is storytelling, it is community, it is showing people how pieces actually fit and function. I love that the two worlds feed into each other. Creating content helps me understand what women want, and running the brand helps me deliver it.
What Is a Piece of Advice You Would Give to Women Who Want To Build Their Own Creative Business?
Starting anything new is scary and you probably will never feel “ready” So my advice is to start before you feel ready, just go for it. Your first try does not have to be perfect, it just has to exist. Be consistent. And you are going to make mistakes, learn from every single mistake – it just makes the next time or collection or drop that much better.
What does the name HOW DO YOU WEAR THAT™ mean to you today?
It is a reminder that there is no single right way to dress. Style is personal. It is playful. It is yours. HDYWT started as a question for my audience, and now it’s a little world we have built together.
What is next for you and HOW DO YOU WEAR THAT™?
I am always working on new designs, new fits and a lot of growth on the horizon, all rooted in the same values. My goal is to keep creating pieces women feel amazing in, and to keep growing this community in a way that feels very me.
