Chapter 2: Sailor Hats

Sailor hats are the answer to everything. Plus: what I pre-ordered for fall.

I used to think I wasn’t a hat person. It took me years to grow into being a “hat person”. Wearing a hat, especially an exceptionally oversized one, takes extreme guts, audacity and chutzpah. It might be the closest sartorial translation to wearing red, or black lipstick. But the secret to wearing hats is actually not caring whether or not they “work” or perceivably “look good”. Because the best kinds of hats are all a little unhinged and slightly deranged—the kind of thing that takes total control of an outfit.

Wearing a hat in 2023 feels like a rebellious kind of thing to do. It’s laterally equivalent to donning a blossoming and billowing babydoll dress that takes up as much space as possible. If you slip on a hat, people may be forced to distance themselves. I was recently combing through the iconic milliner Philip Treacy’s massive book (I highly recommend it for any hat lover) and the legendary editor Isabella Blow was quoted: “Fashion is a vampiric thing; it’s the hoover on your brain. That’s why I wear the hats: to keep everyone away from me. They say, ‘Oh, can I kiss you?’” I say, ‘No, thank you very much.’ That’s why I’ve worn the hat. Goodbye. I don’t want to be kissed by all and sundry. I want to be kissed by the people I love.” So, let me introduce you to the sailor hat.

Vaquera spring 2023. Courtesy Vogue Runway

S.S. Daley fall 2023. Courtesy Vogue Runway.

The sailor hat is exactly the kind of headpiece that verges on costume and absurd fantasy. Depending on its shape, it can skew pirate, fisherman or primordial pilgrim. My favorite kinds are literal: wide brim, stiff fabrics and if you’re lucky, contrasting piping or maybe, a ribbon on each side. A few of my favorite recent examples on the runways? Vaquera opened its spring 2023 show with acid wash denim jorts, a matching cropped jacket and a golden bustier paired with a navy sailor hat, its ribbon cast aside like a lone piece of kelp. The label also showcased the sailor hat in acid wash denim, chocolate brown shearling, black vinyl, classic starched white cotton and my personal favorite: printed with the American flag. And then there was S.S. Daley—which showed a selection of sailor chapeaus that straddled the line between baker boy toppers and sleeping caps.

Sailor hats are an instant classic for delivering fantasy fueled character creation in fashion. John Galliano loves them. Just look at Dior spring 2011. The collection itself mirrored his final walk outfit; a pirate get-up, his hair done up in two fishtail braids (coquette girls everywhere would be proud). Then again, he’s doubled down on his version of the sailor hat at Margiela countless times. For Margiela spring 2020, he shifted through the noise of uniforms and hats worn by authority figures: Catholic nuns, militant workers, nurses et al. The results were hats that riffed on all these different aesthetics; shades of sailor hat mixed in with military berets here and there. But I’m partial to Prada’s spring 2016 versions. Layered up, deep in meaning and paired with off-kilter, undone corsets, laced-up boots, printed button-downs, collars, keychains and little books hanging off everywhere.

Prada spring 2016. Courtesy Vogue Runway.

Margiela spring 2020. Courtesy Vogue Runway.

Dior spring 2011. Courtesy Vogue Runway.

What’s interesting about the sailor hat is the deep connections with war and change. And maybe that’s why it feels so ubiquitous right now. As Sarah Mower wrote in her Prada fall 2016 review for Vogue: “The sexual and historical portents carried by that one little white cap, on a woman, strongly evoke World War II and sweethearts at home, and tarts on the dock—just at a glance. On men—these were first shown on boys in the Prada menswear show in January—they again bring up the imagery of war, and the stock symbolism of homoeroticism. Sailor caps: They were sweet little nothings thrown on the backs of girls’ heads, but they also reminded us that there is a war going on.”

In January, when I was in Paris for couture week, I met with Ruslan Baginskiy, a Ukrainian hat designer who I’d previously met at Ukraine Fashion Week a few years ago. He told me about what it was like going back and forth between Ukraine and Paris for fashion week during the war. Is this what modern war is like, I wondered. I could never even imagine. But sure enough, he too designs an incredible sailor hat.

I had on my list to buy Vaquera’s sailor hat, but before I could get to it, I came across the perfect vintage rendition. I spotted it at Recycled Style, one of my favorite vintage spots in Montgomery, New York, a few hours away from the city.

Vintage hat with sailor hat vibes, by Geo W Bollman

Maybe, just maybe, the sailor hat is the fashion hero we so desperately need in these extremely strange and scary times. In my opinion, the sailor hat works best when styled one of two ways. Either in total opposition, or with an unnerving take on uniform dressing. I loved pairing my vintage sailor hat with a striking neon tulle dress with a lace-up corset and a black coat scattered with bows. It’s everything a structured, militant and orderly hat wouldn’t normally encounter. This is a natural law of disobedient dressing. Otherwise, I love following the formula as seen by Prada and Margiela. Take other elements of uniforms and orderliness and mess. them. up. Wear a lace-up corset and turn it backward, leaving it untied a little bit. Sport a dirty white button-down. Try baggy slacks with a big, crystal covered cowboy belt.

These are my favorite sailor hats to shop now at every price point. Plus, keep scrolling to see the pieces I pre-ordered for fall.

Vaquera Gender Inclusive Faux Leather Sailor Hat

The sailor hat to end all sailor hats. In shiny black vegan leather, it’s perfectly subversive and weird.

Classic Unisex Sailor Hat

The ultimate, classic sailor hat—for a little over $10. Perfect if you’re new to testing out the waters of wearing hats.

1960s Lake of the Ozarks Sailor Souvenir Hat

Some of my favorite kinds of sailor hats are vintage tourist sailor hats! Like a more high fashion version of the tourist baseball cap, and they’re usually really affordable, like this option for a little over $20.

Charles Jeffrey Loverboy Navy Sailor Hat

I love a denim sailor hat as proof of concept that you can truly wear a sailor hat anywhere. This is about as everyday as they get.

Vintage French Sailor Hat

A vintage sailor hat of the French variety is extremely New Wave film heroine. Anna Karina was a style icon for a reason.

‘90s Era Gaultier Jeans Denim Sailor Hat

Jean Paul Gaultier mastered nautical style and flipped it on its head. Enter, any and all sailor hats from him: instant fashion history.

Pink Flower Admiral Captain Hat

An offshoot of the sailor hat is the captain style hat. I don’t love these as much as a classic sailor hat, but, I promise, these work extremely well when they’re obscenely cheesy: with strange names or glaring prints. Easily worn in an ironic way.

Now, for what I pre-ordered for fall!! This next section is exclusive to paid subscribers, so if you haven’t already, please consider subscribing for $5 a month for access to exclusive in-depth shopping guides and shopping tips. Also, tune in next week for an in-depth, paid subscriber-ONLY exclusive guide to shopping secondhand bags. <3