This may sound crass, but my friend and I think that ‘Fleet Week’ is the funniest thing in the world. Every year, we joke that this is the year that Fleet Week is going to really take off — that everyone is going to call out of work, put on their best stripes, and head on down to the piers.

For those not in the know, ‘Fleet Week’ is an annual event that takes place primarily in New York to honor active-duty maritime service. For one week, the Navy, U.S. Coast Guard, and Marine Corps dock their ships at Manhattan’s Cruise Terminal and “let loose.” It’s an opportunity for citizens to meet military personnel, tour U.S. ships, and become educated on two-hundred-and-fifty years of sea service. It’s also an opportunity to party hard with men in uniform.

Don’t get it twisted — we mean no disrespect toward Fleet Week. We just get a kick out of the spectacle. There is just something so patriotic about New Yorkers throwing on an anchor bracelet and partying with real sailors. Its earnestness is as silly as it is charming. 

But after years of making good-natured jokes, it seems that a growing fashion trend may be catching up to the punchline. These last few months have shown a tremendous rise in nautical-inspired fashion. I can’t quite tell when it started — perhaps in between the throes of whimsy and blurred edges of twee — but when Blondita teased the release of a limited-edition sailor hat last July, I started paying attention. 

I knew this was not a one-off event when, only a few months later, Mode Mischief dropped a “seaside-inspired” summer capsule collection, complete with sailor-inspired dresses. And even more recently, Free People has launched sailor hats for their Spring/Summer collections — followed by cult-brand OMIGHTY launching a “sailor scout” baby tee for sale. 

What came first: the sailor or the trend? This sudden surge in sailor-chic outfits appears to be the result of a socio-digital tension pitting fashionista against fashionista. As of late, the competition is not rooted in the survival of the prettiest, but rather the survival of the whimsiest. It is as though whimsy is ancillary to authenticity, except authenticity has been repackaged as an aesthetic rather than an intrinsic courage to be yourself.

Back in the day, wearing something on-trend for the sake of being on-trend came with the risk of being labeled a poser. Today, being a poser has circled back around to being ironic, and therefore paradoxically authentic. Stepping out into the street wearing a sailor hat is so ridiculous, that to wear one so boldly suggests a measurable amount of seriousness. In other words, it’s so unreal that it becomes real.

Is this art that provokes thought, or merely whimsymogging? 

I don’t have the answers, but it’s worthwhile to explore while breaking down the quintessential “sailor chic” outfit. To take party in this trend, one must primarily opt for navy blues, crisp whites, and cool-toned reds. However, teal blue, aquamarine, and coral are exceptional in the color palette as well. We’re thinking oceanically, of course.

The feminized sailor silhouette certainly puts the “naughty” in nautical — mini dresses, knee high socks, and white bibs are commonly seen in the objectified sailor girl. To go more traditional with the trend, one may opt for sailor-button trousers, striped polo shirts, and pearl earrings.

All of these may or may not be worn with the sailor hat. The sailor hat, if it has not been gathered by now, is the impractical accessory that I suspect will become the most sought after piece in this brief trend. Slapping a bowl-shaped, visorless hat onto an otherwise “normal” outfit will be the ironic genuinity that captures the fashion scene. (I want to point out that I find it ironic that CNN called nautical wear timeless and practical. Timeless, maybe. Practical?)

In earnestness, the trajectory of “sailor chic” has a somewhat knotty history. It began with Queen Victoria commissioning a Royal Navy sailor suit for her four-year-old son, future King Edward VII, to be worn on a yacht. Little Edward was then depicted in a painting wearing the infamous suit, which sparked a frenzy among the public. The demand for nautical-inspired children’s clothing was born.

Around World War I, sailor-inspired fashion was reintroduced in womenswear as a symbol of national pride. This, ultimately, became co-opted by Hollywood starlets who reimagined sailor suits as sexy beachwear. 

Then, in the 1980s, sailor chic was revived yet again as a bold fashion choice. This time, it took on a more studious silhouette with 1960s influence: high waisted pants, naval buttons, and striped polos. 

Finally, in the early 2010s, nautical-inspired twee looks had a brief life on shelves. High-waisted shorts with naval buttons, peter-pan collars with piped hemlines, and white cat-eye sunglasses were the coveted pieces of the reimagined sailor girl: a sexy but playful imitation influenced by rockabilly fashion, twee’s prevalence, and the rise in manic pixie dream girls. Sailor hats were around, but as more of an ironic statement — a costume rather than a fashion choice. (Also, Leg Avenue’s famous Halloween costumes deserve an honorable mention in the distribution of sexy sailor girls as a cultural reset.)

The question is whether 2026 will succeed in its attempt to reinvent sailor-chic as a quirky niche rather than a sex symbol.  But with how quickly the internet cycles through microtrends, it’s more than likely that the ship has already sailed on sailor chic.

I say this because if a store as commercially successful as Free People is selling sailor hats, we are already at the peak of the trend. But let’s be honest — have you seen a single person outside of TikTok wearing a sailor hat as a fashion statement outside? I haven’t. Not yet, anyway. Fleet Week could change that, but for now, I think the trend will quietly exit as quickly as it silently crept up on us.

Sailor chic is impractical for most daily wardrobes — as sailors are wearing a uniform with purpose, after all, and not a costume. But if you, too, are delighted by nautical-wear and want to ride this quick wave, keep your eyes open for all of the maritime pieces available at this time. 

Holy Thrift has a few modest options to get you started on seas-ing the day. 

Shop the curation in order:

1. https://holythrift.com/products/multi-button-sailor-short-in-white?_pos=1&_sid=19921ff0c&_ss=r 

2. https://holythrift.com/products/red-leather-boots-8-5?_pos=4&_sid=3fd22d379&_ss=r 

3. https://holythrift.com/products/multi-button-sailor-top-in-black?srsltid=AfmBOorCw_vFCven6DIjPkYtfG2AZAs3x8hGDeE85j3in1hM3LNsoLwu

4. https://holythrift.com/products/starz-stripes-mini?_pos=1&_sid=6f8a53eaa&_ss=r 

5. https://holythrift.com/products/michael-kors-navy-blue-bag?_pos=1&_sid=11411a204&_ss=r 

6. https://holythrift.com/products/yacht-angel-charm-kirks-folly-watch?_pos=1&_sid=e24327193&_ss=r 

7. https://holythrift.com/products/heart-of-pearl-necklace?_pos=6&_sid=efd35ac96&_ss=r 

8. https://holythrift.com/products/navy-blue-elastic-belt?_pos=3&_sid=11411a204&_ss=r 

9. https://holythrift.com/products/striped-cashmere-ruffle-cardi-s-m?_pos=11&_sid=6f8a53eaa&_ss=r 

10. https://holythrift.com/products/vintage-polka-dot-babydoll-dress-s?_pos=8&_sid=f1ca0ec19&_ss=r