by Angeline Kai Vibar

Looking into a mirror and seeing Stede Bonnet

There’s surprisingly a lot you can learn from a pirate experiencing a mid-life crisis—especially when said pirate happens to be a gentleman in silk waistcoats who looks like he’s perpetually stumbled out of a high-society tea party straight onto a pirate ship. Enter Stede Bonnet, the protagonist of Our Flag Means Death, a character I found weirdly relatable in the most unexpected ways.

Video accompaniment to my blog if you’d like to hear me narrate! :)

Stede is the epitome of contradiction. Raised with the refined air of a gentleman, he decides to throw caution (and etiquette) to the wind and becomes a pirate. As someone who, a few years ago, left behind a more predictable life to embark on a journey filled with self-reflection, art, travel, and many, many dark nights of the soul (lol)—I see a lot of myself in Stede’s internal struggle. He craved freedom but was also constrained by the ideals of a life he didn’t quite fit into—a theme I know all too well.

I grew up in a blend of modern and traditional Filipino culture. While I had the exact expectations of stability and success, I watched my parents break generational curses, seeking more for themselves and, in turn, more for my brothers and me. Though my path often felt as winding and uncharted as a pirate’s map, like Stede, I couldn’t shake the desire for something beyond the boundaries of what I was “supposed” to do.

Blackbeard and Stede Bonnet take on the shores of Venice Beach. In heels!

Cue the photoshoot Tina and I planned—an ode to our unlikely heroes, Stede Bonnet and Blackbeard, but with a little feminine twist. Tina and I have always been obsessed with fashion and cinema, dreaming of recreating iconic scenes. Tina came through with some fantastic set design pieces she treasure-hunted from Goodwill. Artist David Mack’s beachy patio served as the perfect backdrop for our ship. Our shoot wasn’t just about dressing up; it reflected how we’ve always seen ourselves in the art and media we love. Over the years, cosplay has become a form of storytelling for both of us.

I wanted to embody Stede’s contradiction—the clash of luxury and ruggedness—so I styled myself in a yellow 100% silk bustier top and matching taffeta skorts from designer Kim Shui, a fellow Asian-American creative who inspires me. This outfit was inspired by Stede’s so-called “battle jacket” in the scene where he’s sitting in his library on the ship, contemplating the insane choice he just made to leave his perfectly cushy world for a pirate’s life. The soft elegance of the silk contrasted perfectly with my vintage leather lace-up Prada boots. My goal was to combine the character’s more frivolous, elegant roots with the person he wanted to become—silk on top, leather boots on the bottom, walking in the throes of a true grit, pirate-like direction. I’m sure Stede would appreciate the consideration.

Adding a pearl bustier from Akira was a nod to Stede’s privileged, over-the-top background, and of course, with our ocean theme, pearls just felt right. As for my jewelry, I added Rimor’s 3-Row Venus Heart choker, inspired by my love for Vivienne Westwood’s iconic pearl choker. The Venus choker uses fresh-water pearls, and as a sucker for vibration-raising anything, I would highly recommend this beauty as an alternative if you were eyeing the glass-based pearl Vivienne Westwood Bas Relief Choker. (It’s still on my wishlist regardless, haha!) Freshwater pearls are said to help the wearer tap into inner wisdom as well as improve emotional intelligence. Basically, your girl needs all the help she can get. I also added my favorite Vitaly, Eyeba, and Jean Rachel rings to the rugged luxe look I was going for.

Under the guise of a period piece comedy, Our Flag Means Death touched on unrealized dreams, personal transformation, and learning to be honest with oneself. At first glance, the show might seem like just another cartoonish pirate adventure, but underneath the humor and swashbuckling, it delves into deeper themes of identity and self-acceptance. The show also doesn’t shy away from the consequences of a person’s actions when they reach their breaking point. When a person isn’t being true to themselves, their loved ones can get caught in the crossfire. Stede Bonnet’s journey isn’t just about escaping societal expectations but also about discovering who he truly is, even if that version of himself doesn’t align with what’s expected of a pirate—or even a gentleman. The show beautifully captures the tension between trying to fit into a role imposed by society and the messy, unpredictable journey of becoming your authentic self.

..In my pajamas? N-no—this is my battle jacket!

Through this creative exercise, I found that fashion—like Stede’s pirate life—is about embracing contradictions. Fashion is rarely straightforward or bound by the rules. It’s a playground for self-expression, where different styles and elements that might seem incompatible at first glance can create something unique and reflective of the person wearing them. In fashion, as in life, contradictions can be empowering. Pairing soft fabrics like silk with rugged elements like leather boots shows the duality within us—the desire for comfort and challenge, elegance and toughness, tradition and rebellion. These opposing forces can live together harmoniously when we stop trying to compartmentalize ourselves and instead lean into the complexity of who we are.

Maybe that’s what Stede and I have in common—the desire to be free, to be ourselves, and to break the mold in silk and leather while doing it. For me, that’s what fashion and self-discovery are about—blending the unexpected, embracing contradictions, and, in doing so, stepping into a truer version of ourselves. Like Stede, I’ve learned that breaking the mold can mean taking risks, wearing things that feel at odds with the environment or expectations, and ultimately, finding liberation in those choices. Just like Stede’s pirate crew learns to accept him for the unique leader he is, we too can find power in fully embracing our contradictions—both in how we present ourselves and in who we allow ourselves to become. - akv

Pirates, Pearls, and Prada

angeline kai