I’m in My Pirate Era. Here Are 5 Pieces I’m Shopping This Fall

Walk the plank—er, runway

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Still from 'Our Flag Means Death.'
Aaron Epstein/HBO Max

When season two of Our Flag Means Death premiered earlier this month, I finally hopped on the bandwagon and binged the pirate-centered Max series in a matter of two days. Due to its stellar reviews and strong fanbase, my quick obsession with the show didn't come as a total surprise. However, my love for the fashion sure did.

In case you've never seen it, the swashbuckling rom-com feels like Ted Lasso combined with Pirates of the Caribbean, as it follows a group of (mostly) men in what is typically perceived as a hypermasculine, toxic environment: a pirate ship. But in this world, the buccaneers are actually quite sensitive and supportive of one another, and they're led by a stylish, aristocratic gentleman named Stede Bonnet (a real-life pirate from the late 1600s who loosely inspired the series).

Our Flag Means Death has plenty of things to love, from an iconic Taika Waititi performance as Blackbeard to loads of celebrity cameos. But for me, I spent the whole first episode fixating on the fashion. Where can I get those shoes?!, I thought to myself as Stede (played by Rhys Darby) strutted around his ship sporting a pair of period oxfords adorned with a white bow on top. Suddenly, I found myself noticing all kinds of eye-popping ensembles. The frills, the colors, the stitches—I couldn't look away! Plus, the show embraces its sartorial side, like in one episode where Stede won't get rid of a coat, even though the rest of his crew believes it to be haunted.

Now, as season two comes to an end, I've found myself fully immersed in my pirate era, and these are five items I'll be shopping so I can embrace my inner-salty sea dog (without looking like I'm dressed for Halloween).

How to Copy Rory Gilmore’s Fall Style for All Your Dark Academia Dreams

Funtasma boot.

1. Funtasma Women’s Victorian Boot

  • Size range: 6–12

Stede Bonnet’s shoe game is unmatched in Our Flag Means Death, and we think if he had lived in the same time period as Carrie Bradshaw, the two would've gone head-to-head in spending the most money on footwear. If you're looking to emulate Stede’s shoe collection, try this Victorian-style boot, which feels vintage, but also fits into the current trend of dark academia.

Neiman Marcus

2. Cinq à Sept Faux-Leather Pants

  • Size range: 0–14

As Blackbeard, Taika Waititi wears a *whole* lot of leather on Our Flag Means Death. But while an all-leather outfit might look a little gimmicky, we're eyeing these pants from Cinq à Sept, which would be the perfect fall staple to match with a sweater or button-up (and they’re also offered in a tobacco color).

Neiman Marcus

3. FRAME Tie-Neck Long Sleeve Silk Blouse

  • Size range: XXS–XL

With fewer ruffles, a blouse with a big bow in the front will come across as preppy and stylish, rather than seeming like a “puffy shirt.” Try this FRAME silk top, which is also available in blush. And if you're not feeling the bow, let the neck ties hang for a more understated look.


4. Mango Floral Linen Vest

  • Size range: XS–L

Sweater vests have been trending for quite some time now, yet we can't help but fawn over Stede’s numerous embroidered vests on Our Flag, which he usually pairs with colorful frocks and frilly tops. For a more modern update, we're going to snag this floral vest from Mango, which we'd recommend layering over a button-up or turtleneck (or wearing it on its own during the hotter summer months).


5. Anthropologie Wide-Placket Popover Top

  • Size range: XXS–XL

If you prefer to go for that casual, breezy look—like you just landed on the beach and you're ready to sip on a rum-based drink—try this flowy pullover top from Anthropologie, which simultaneously effuses effortlessness and style.

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Associate Editor, News and Entertainment

Joel is the former Associate Editor for News & Entertainment and has been reporting on all things pop culture for over 5 years. Before working at PureWow, he served as a...