Nantucket Reds
What they are, and how to not wear them
Collars get popped, or they are button-downs, there are boat shoes and white cavas trainers, a proper blazer if the occasion calls for it. There are khaki pants worn with blue shirts and navy sweaters. I revel in this stuff, in the lazy, roughened up expression of it all, which came about in the eighties with the changing of the guard from Brooks and Press to Polo and J. Crew. That is to say, I feel rather comfortable in this world, and yet there is somewhere I will not go, a piece of clothing which remains— dear reader I can only apologies for this— a prep too far.
The Prep Club is in session, check last week’s issue of THE RADAR (our fortnightly magazine) here for thoughts on Bronson MFG. and how we can open the door to heritage fashion. Also, make use of The Directory, the alphabetised, as-comprehensive-as-possible guide to heritage, niche, and vintage preppy menswear:
And if you’re new to this, or want to read a long list of very, very nice clothes you can check The Kit List, updated this week:
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To get things straight first of all, Nantucket Reds are brick-red-faded-through-to-pink, sailcloth trousers. Cotton sailcloth is the same thing as duck canvas, with “duck” being a bastardisation of the Dutch “Doek” for deck; it is a densely woven, rigid canvas. Reds have a lengthy and storied origin (Christopher Sharp manages a fairly comprehensive history here, even if I disagree with him on fronts which will shortly become apparent). To summarise, very briefly, red canvas trousers for sailing first came about in Brittany, spreading to England and America thereon, the red colour being inspired by tanbark coated sails. More than any of this though, as I see it, Nantucket Reds are something to clown on.
What you must understand is that I’m looking at Nantucket Reds with my feet upon a very different island. Here in the UK the ignominy of the red trouser has been largely inescapable for many years; though, this is possibly quietening down a bit as of late. I’d wonder if that comes from the eyre growing so strong that people simply stopped wearing them. Red trews were, for the longest time, the symbol of the obviously abhorred toff, then the equally hated hipster, and then the discourse sort of died a death in the mid twenty-tens, and there hasn’t been much talk of them since.
I take that as a quiet but important sign that our signalling garments have changed, the British think-pieces on red trousers in the first half of the last decade feel very similar to those suspicious of the quarter-zip and its many connotations today. Which perhaps re-opens the question of whether Nantucket Reds could fly in a world where fashion signalling isn’t dead, but probably smells funny. My personal answer to that is, nah.
See, the first problem is that Reds have never really been that “cool”. When the rest of prep had a rebrand, taking on this far more easy-going, understated connotation, Reds were still very much a signalling tool, a members only affair, and they were far too loud to fit into that aesthetic besides. Yet, they do have one thing which we all like very much in heritage clothing: they’re meant to age, and to show the life they’ve lived, a particular kind of life too, they won’t fade properly unless they’re around sun and sea water. For this I find in my heart a secret adoration for Nantucket Reds, which I feel I need to hide away as if it were some perversion. Wrapped within that I also feel a hubris which I have written about before, a sneaking suspicion that I could make them work. I’d take them away from the navy blazer for certain, and would have to go about sourcing some with a nice wide fit acceptable to my Gen Z ass, but there’s some sort of expression in there that I can see working. I want to give them the treatment they never got from the J. Crew and Polo adverts.
So will I? Maybe, but almost certainly not. Reds to me serve as this reminder that though I might speak the language, I am decidedly not of this world, and I will never be, I should not wish to be. I only aspire to wealth in the way that all who lack it do, I long for the comfort and for the freedom but I do not dream of a life entertaining gentry or worrying myself with stock portfolios, and I don’t believe in private schooling. The reputational, perhaps moral, fuzziness around Reds— the sort of thing that makes you say “hmmmm, not quite sure about that one chief”— was once an issue of signalling. Now, however, I reckon it’s more broadly an issue of authenticity. There’s an unfortunate bind here where if one is to sport a pair of red pants they’re either being inauthentic or authentically a bit of a knobber. I don’t think we’ve found wealth all that cool for some time. Even if it’s had a place in the public interest it’s been in the from of “quiet luxury” into which Reds don’t so neatly fit. Anything so closely associated with a cushy, struggle-less lifestyle is liable to fall victim to a decided lack of edge. It’s only by playing with their negative connotation, or by unsettling the notion of authenticity, that I can find a sort of danger, which just might be alluring. There’s a thrill to be had in rocking a garm with a poor reputation, within reason, obviously.
Returning to that “change of the guard” that I mentioned right back at the beginning, I think that was the precise moment that a wall was built up around Reds. The advent of the catalogue brands, J. Crew and Land’s End, marked the dissemination of the “preppy” style out to a far wider audience, and they just left Reds behind. Perhaps because they weren’t commercially viable outside of the island itself but the reason itself isn’t very consequential. What I think matters is that whilst prep became a style for almost all of America, Reds were not a part of that widespread adoption. They remained the calling card of wealth, and thus stayed an undeniable and impenetrable piece of clothing for one group and no one else.
It’s important that we make boundaries in our fashion, else we’d never really know where our selves end and the rest of the world begins. An identity cannot be infinite, we cannot be everything, and as with many things it’s probably easier to define ourselves by what we are not, rather than who we are. But, as with any frontier, there’s always a question mark about it, a big old what if…
Prep Club adjourned, happy sailing.










The “real” Nantucket Reds – from Murray’s Toggery Shop – already have the wide fit you’re looking for. I sympathize about their connotations but, where I live in New York City, not far from their homeland, I don’t think I have ever seen another person actually wearing them, and thus they have very few real-life connotations at all.