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Caitlyn Warakomski

Caitlyn Warakomski shares personal style and outfit ideas, co-founded the clothing label HOW DO YOU WEAR THAT, and writes Caitlyn’s Edit on Substack.

900K+social following
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Latest

Caitlyn’s happenings, collected from public sources, plus their backstory and Starbook, where fans write.

Known for

Overview

Work
Fashion creator, writer and clothing-brand co-founder
Started
HOW DO YOU WEAR THAT fashion blog, June 2015
Brand
Co-founded HOW DO YOU WEAR THAT with Brendan Slawson in 2020
Early milestone
More than 110,000 Instagram followers by March 2018

Mini bio

How it started.

Caitlyn launched HOW DO YOU WEAR THAT in June 2015 after a marketing layoff. Friends and family had inspired the name by asking how to style things. Daily outfit posts grew into a business; about a year and a half later, Caitlyn left event marketing to create full time.

From an outfit to a label.

In early 2020, Caitlyn made a tie-dye T-shirt and biker-short set. Followers asked to buy it, and the first charity pre-order sold out in a minute. Caitlyn and Brendan Slawson turned that demand into HDYWT, expanding into locally made clothing.

Style, in real life.

Caitlyn’s content connects outfit ideas with the clothes they design. In 2026, that included a wedding wardrobe and the Celeste Gown collaboration with Alexis Levan. Caitlyn’s Edit adds shopping guides and personal writing to the Instagram and TikTok posts.

Creditschronological, newest first

Design

Writing and digital

Quotes

Your first try does not have to be perfect, it just has to exist.Caitlyn Warakomski, All My Friends Are Models

Advice for women starting a creative business; interview linked in sources.

Trivia

  1. Caitlyn’s early styling experiments included turning a printed tablecloth into a dress and a skirt.
  2. Caitlyn and Brendan met while working summers at a golf course, before they started dating.
  3. The couple’s first dance was to “The Face” by Kings of Leon.

Find Caitlyn

Follow Caitlyn for outfit ideas, new designs and the stories behind them.

Are you Caitlyn Warakomski?

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