365 Pirate Outfits Challenge
Why do I keep dressing like a pirate? It’s the I’ve asked myself a thousand times.
The Short Answer:
For the fun vibes. My historical fiction novel, The Determined—based on real-life pirates Anne Bonny and Mary Read—comes out in February 2026. History had a lot of commentary about these rebel women, but especially about what they were wearing (some things never change). Dressing the part, in anticipation of this book release, felt like a fitting way to celebrate them and their complex legacy.
But that answer barely scratches the surface.
The Very Real, Very Personal Answer:
I recently went for a walk and shared a vulnerable video where I explored this question of why I, an adult woman who dislikes attention, keep dressing up as a pirate. The truth is that I dress pirate-ish all the time lately, including when I’m not posting or writing about pirate things. I’m clearly not doing this for an audience; I’m doing it for me.
Why?
I noticed that when I published my debut novel, If the Tide Turns, in March 2024, one of my favorite parts of my tour was dressing up. I went full cosplay and challenged myself to have different outfits for each of the twenty-five stops on my tour.
The tour ended, but the clothes journey did not. Sure, it wasn’t full costume-pirate, but if I could make anything vaguely or not-so vaguely nautical or pirate-inspired, I leaned in.
Again. Why?
To throw an anchor right down to the bottom of the question, I can think of a few honest reasons:
1. A Reaction to Modesty Culture
I grew up in a culture that emphasized modesty, particularly in how girls and young women dressed. Everyone has different opinions about this, but my own experience included a lot of pain.
One of my first core memories was of swinging on the monkey bars when a fellow kid scolded me for having a tank top that was an inch thinner than the playground rules. I’m not sure I’ve ever thought about my bare shoulders the same since.
If it wasn’t that kid, it would have been someone else. I grew up measuring the length of my shorts from my fingertips, hand-sewing sleeves on formal dance dresses, and measuring the goodness of the people around me based on whether or not they wore two-piece swimsuits.
My prom dress, a halter top, didn’t have a design that I could sew on my own sleeves. So I went to a fabric store and matched it with a shawl. The effort did not spare me the moment of getting in the car with my date, having to ask him why he was visibly upset, and have him say, “I’m worried about what my mom will think of your dress.”
The wound, which I’ve only touched on with more minor examples, grew with time. As an adult, wearing a dress that flashed my shoulders to a friend’s wedding, my partner who I loved more than life itself, took one look at me and said, “You’re better than this.”
Even now—years later as I’ve made peace with my culture and place within it—when I post a picture of myself with any shoulder showing, I instinctually feel afraid. Shunned. Judged. Even when I know the truth: that I’m not trying to be seen as “hot” or subversive or solicit comments.
I don’t know how common it is for many other grown women to feel this fear, but I do. I wonder if I will forever.
But dressing as a pirate is me, raising a blade against that bone-deep fear.
2. To Show Kindness to Younger Rachel
For a number of complicated reasons, clothes were not a priority for me growing up. My mom dressed me like a doll up through elementary school, but adolescence was hard on both of us. Plus, my parents had divorced by then, and my mom was living off of food donated by our church. There wasn’t money for clothes shopping.
I owned one pair of pants when I began seventh grade. I rolled them up different ways each day so people couldn’t tell it was the same jeans. I could not bear to look at myself in the mirror. And yet, it was around this time that I first watched Pirates of the Caribbean. Each Halloween after, I dressed up as a pirate.
Up until recently, I still didn’t really buy clothes. Not even thrifting. I wore things people gave as gifts and hand-me-downs from fashionable friends. My best dresses and shoes were from half a lifetime ago. This was fine, more than fine. But I was missing something of me in my passive clothing choices.
Then I remembered younger Rachel. There was so much upheaval in my teen years, but that was one consistent thing in my life: dressing as a pirate every year until I was eighteen. It was one of the outfits I took with me for my senior pictures.
Younger Rachel knew something that Present Rachel is still learning.
3. To Tip My Tricorn to Real Pirate History
My understanding of pirates has evolved enormously since I was first a young girl, drawn by an overly romanticized view of pirates through Pirates of the Caribbean.
And yet, real-life pirates thought a lot about clothes. I learned that Sam Bellamy, a lead character in If the Tide Turns, dressed in a black velvet jacket—his finest—because it was a statement against the elite he was fighting. “I’m just as allowed to wear this as you are,” dressing like a dandy boldly declared. It was common for pirates to steal the fancy clothes from the nobles they robbed.
Anne Bonny and Mary Read faced this, but as women, everything was heightened. Mary cross-dressed her whole life to afford privileges she wouldn’t have had otherwise. In the end, Anne and Mary were condemned as men because they dressed as men. Much of their court trial documents make a big fuss about what they were wearing.
Sound familiar?
I realize I don’t have to give any of this framing to just keep sharing what I love. But I think the “why” matters, and maybe what we love is never trivial—even and especially as the world burns.
If my “dressing up as a pirate” posts reflect even the smallest shard of hope, joy, or reminder of your own freedom, I hope you wear the things you want to wear, do the things you want to do, and say the things you need to say—so you can better show up for the people and causes you care most about. Joy is radical resistance, as they say.
If all of this appears trivial or vain, silly or weird, you might be right. But also, maybe not. And if it is all for naught, consider this:
Should death claim me, I very well might regret many things. But dressing like a pirate at every opportunity? No. Not only will it mean I wore what I wanted to wear rather than what I was told to wear, it’ll be mean I have the cooler ghost outfit. I’d rather be caught dead forever in pirate clothes than a boring t-shirt.
I don’t know that I believe in ghosts, but I do believe in freedom. And in you.
The Pirate Code, as it relates to my 365 pirate-inspired outfits:
I said 365, not 1 per day. Savvy?
I’m an author, not a fashion influencer (no aspirations to switch ships, either).
I’m not trying to sell anyone clothes. I pay for or thrift everything you’ll see. Brand ambassadors are privateers.
I won’t be replying to comments on or about my body or desirability—that’s the opposite of why I’m doing this.
Questions? “Siri, play “Vigilante Shit by Taylor Swift.”