Preppy Style's Subversive Time
The millennial bring back of boat shoes, at a Miu Miu or Sebago’s near you.
For a good part of the past 12 years, I have always either worn a loafer or car shoe. I didn’t grow up in Connecticut or Maine, I came of age during the aughts in Tampa Bay, Florida. I didn’t grow up in a big boating family, but did spend weekends in malls hanging out at a Hollister or Abercrombie & Fitch, submerged in surf’s subculture. We were a group in the early 2000s that didn’t necessarily surf at the beach, but dressed like they did.
Did your Hollister have a live screening of Huntington Beach, CA? It became such a cool use of technology at a boutique and innovative signifier of its time. Fashion was only just scratching the surface of mass auditorship. And on a Tuesday night the October of 2009, Alexander McQueen’s ‘Plato’s Atlantis’ show, the one with the Armadillo shoes, invented the concept of breaking the internet.
You know the markers of said subversive-prep style. Cotton logo patched t-shirts, knits, oxford shirts, rugged cargo shorts, khaki pants, ripped jeans (a derivative of the punk style of the 90s), rainbow sandals, shell jewelry, tossed hair, athletic sneakers, and boat shoes.
I had one Abercrombie top with the logo stretched vertically in the front that looked as if it had been spray painted onto the t-shirt. It was a period gem that suitably belonged in the past.
Now there’s something oddly appealing about this season’s preppy aesthetic that reminds millennials about our funny and wacky adolescent selves. The pure and wonderful us that was so hard on ourselves, and is ready to ride the wave back.
Maybe it’s that NYT article about adolescents wearing $300 luxury perfume, raising the question, are they being corrupted by mass advertising? How will youth economics impact the sales of Tom Ford’s Tobacco Vanille? Maybe it’s also the harsh political climate on college campuses that’s resonating globally.
Last week, President Biden gave a commencement address at Morehouse College and was faced by pro-Palestinian protests, many students walked out during his speech. It also helps that a Kennedy running for President (aren’t they always?), is in the limelight. But I’ll stick to the shoes for this one.
After all, when a shoe from the past wakes us, maybe it's because it's time to join the dance.
A [30 year old], And The Sea
My style still has preppy undercurrents. A broad cut of it stayed in the aughts, but loafers became a part of who I am. My shoes impact how I’ll get dressed in the morning, whether I’m dressing for the rain or not, or if I need to “add weight to a look”, as
, from the Substack ‘The Cereal Aisle’ expertly put it. They’re a fashion stamp that say, been there done that. Sort of like a postcard from the beach.I like the way moccasins and loafers shape my feet, and that I do not have to worry about lacing them. They look good with jeans, dress pants, and swim shorts, and have that ‘old school’ aesthetic. I like wearing my Church’s loafers on early weekend mornings with pajama trousers to take the dog (hi, Ulysse!) out for a walk. I can wear them at night for dinner.
But boat shoes are a different beast. Or, what Vogue dubbed 'the shoe of the year'. They imply conquering the sea.
I was recently reading a loafer matrix to interpret the subtle differences that exist in construction, shape, and hardware between say, a Penny, a Venetian, and a Car-Driving shoe.
I found this matrix fascinating for a few reasons. First of all, this matrix can be implemented across genders. While women’s wear has more verticals, you can shift looks and edit cuts based off this matrix. As you can see, the Moccasin family ranges from the very casual to suit and tie. Say, a walk along the hydrangea-lined hills of Biarritz or dinner at an upscale haunt in Lake Tahoe.
Boat Shoes, A History
The shoes, dubbed ‘preppy’ and ‘all-American’, have been around since 1935. They were popularized throughout the 20th century as the emblematic ‘East Coast Preppy’ shoe, achieving critical mass status in the 1980’s, when they were published in “The Official Preppy Handbook”.
Sperry’s, originally made with white rubber soles to avoid slipping on the deck, were then sold to the US Navy for its Naval Academy sailors to wear in the 1940s. The nautical style gained White House approval in the 1960s, when John F. Kennedy, known for his slim suits and New England style, would wear topsiders.
Boat shoes have become a staple of the American wardrobe finding their place amongst the North East, college campuses, surfers, and cities like New York. But, is a broader democratization of the boat shoe in store for this summer? Since I started writing this article over a month ago, all signs have pointed to, yes.
The Comeback
Although unexpected, slim-form deck shoes made waves during the Spring Summer 2024 collections at Bally, Miu Miu, and Fendi. It got me thinking a lot about a question I had not asked myself in over a decade, should I buy boat shoes? I’ve been asking around in chats and the answers have proven positive.
While it is fair to say that I am buying into a trend, and can be at times nostalgic about some of my clothes, it had not dawned on me to purchase a pair since I was in high school. And, something about this moment feels like it’s the right time.
The broader consensus is that boat shoes are ultimately “rooted in function, not fashion”, writes Guy Trebay, a reporter for The New York Times. Fashion’s cyclical nature will deem a shoe anti-fashion, with a stamp of criticism attached to it. This is why I am into them, for the same reasons I liked them in high school, except that now I need them for a casual day at the office or to feel closer to the beach.
They feel subversive in that sense, the idea of going against the tide. But it’s also that they imply feeling closer to yourself. To wear something you wore in your teens again in your 30’s is thrilling. And a great idea for summer.
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Have you listened to Articles of Interest’s series on American Ivy? It’s totally worth a listen on how a Japanese fashion book based around American collegic prep influenced so much.
No I have not! But I will note down to do it.
I’ve been wanting to explore this for a while, this style helped influence my way through the world and how I approached my education and so on and so forth. I can only imagine from thinking about some previous runways of the mid-aughts how this could be a pretty big subject. Sometimes experiments surprise, so I’d be curious to see how a major western moment would come together with Japanese influence. Thank you!