I will admit that I have a penchant for adopting entire personalities from the media I consume. If I didn’t have Pretty Little Liars to influence my entire wardrobe and life choices in middle school, who knows the person I would be today (probably better off, but you get my point). If you told me a couple of weeks ago that my current obsession and new style icons would be a bunch of fictional gay pirates, I wouldn’t be surprised… but I would be concerned. Hear me out, though! After a quick binge-watch of HBO Max’s new comedy show, Our Flag Means Death, I wholeheartedly believe that pirates were some of the OG trendsetters.
Recently, I have been in a rut when it comes to my style and wardrobe. There are only so many ways I can wear my Ivy Park sweatpants before I reach cartoon character outfit repeater levels. Everything changed, however, when I saw a strangely well-dressed pirate watching the sunrise on the ship deck wearing his custom floral silk robe.
The show’s main character is based on a real person who historians often referred to as the “Gentleman Pirate.” His real name is Stede Bonnet, but the nickname stuck because he was a rich and extremely posh member of society before getting bored and deciding crime was more his vibe. While watching, I instantly became enamored with his wardrobe on the ship. Tucked away behind a secret door, he brought his entire custom wardrobe on the ship. It reminded me of Jade’s secret closet in the live-action Bratz movie: completely unreasonable, over the top, yet still the object of all my wants and desires. Bonnet, throughout the entire season, even while fighting and looting, always stays true to this over-the-top aesthetic.
A lot can be said for dressing the way you want, no matter what people say. Pirates are often members of society who felt they had no place or didn’t belong and needed an escape. Their life at sea offered a space for them to be accepted as their true selves, whether that manifested itself as head-to-toe leather or lace cuff links. As cheesy as it sounds, I really relate to these pirates’ desire to be themselves no matter what. At our core, we are a generation of rule-breakers when it comes to self-expression. So, let’s say goodbye to playing it safe, and start dressing weird!! It is so easy to get caught in the pressure cycle of microtrends or self-conscious about how you will be perceived when you walk out the door. I, for one, hate being perceived!! But! From here on out, when I feel anxious about wearing something different, I’m gonna channel the Gentleman Pirate, aka the OG pirate slay.
Words by Anna McGregor.
Graphic by Danna Macias.