The Prep Club

The Prep Club

Ivy Piracy

THE RADAR // Issue #34

Callum Giles's avatar
Callum Giles
Jun 05, 2026
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Welcome back to THE RADAR, The Prep Club’s fortnightly mini-magazine keeping you in the loop of what’s hip in the sphere of collegiate threads. You can attend last week’s meeting here for a discussion on Nantucket Reds, and why I just can’t bring myself to wear them.

Here’s what’s on the radar this week:

— A rugby side, a secret society and an Ivy emblem

— Why I can’t have nice things

— A sweatshOrt buyer’s guide

— Anatomica x Sebago


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Ivy Piracy

We tend to deal in fairly broad strokes with the Ivy style canon, types of jackets, shirts and trousers, or zooming even further out into a prevailing attitude, but I wanted to talk today about a single motif, and the cultures from which it originates.

The connection between ivy style and the skull and crossbones is a little fuzzy to trace. It’s first prep-adjacent appearance crops up in England, one of the earliest rugby football teams, the Rugby School’s own School House side, wore a skull and crossbones on their jersey. This lineage is likely what inspired the use of the skull and bones by Rugby Ralph Lauren in the early twenty tens as a part of the “youth” focus that brand chased. Note that’s not just a connection made because of the name, Rugby RL produced actual skull emblazoned rugby shirts in much the same fashion as those worn by the School House team. My old nemesis Rowing Blazers have gotten in on that action too, with a more faithful reproduction of the old jersey. The Rugby Company produces their version in England to this day.

That’s not the only thread between the skull and crossbones and “Preppy” fashion, though. To go forwards we need to drop the cross and talk about the infamous Skull and Bones secret society at Yale. As is usual I’ll skip the full history lesson and direct you to the Encyclopaedia Britannica should you need bringing up to speed, I suspect y’all in the States know about them pretty well already— I don’t recommend doing much more digging either, people get their tin foil hats out and it all gets rather uncouth very quickly. Nonetheless, the society has, allegedly, made clothing with skulls and bones upon them, namely scarves and ties, though only ever for members, and when there’s only fifteen admitted a year you can imagine there isn’t much product. Given its Yale we’re talking about, naturally these have been produced by J. Press, who’ve since made commercially available skull ties too. However, whether these are inspired by Skull and Bones, by the School House rugby side, or indeed just because people think the skull and crossbones looks cool, who’s to say. My favourite place that the motif crops up is on velvet slippers made by Crockett and Jones and Trickers, and similarly trying to trace where the lineage might have come from is tricky. These being British brands might imply the former lineage, but the fact that they’re making formal wear might imply the latter. I did ask, neither replied, I don’t blame them.

It seems rather apt that such a morbid symbol, let alone one attached to a secret society, would remain shrouded in mystery. In this case I believe both lineages have come together, with the skull and crossbones an accepted Ivy motif, if a bit of an ostentatious one.


How to own nice clothes

Despite having written about clothes for some time, it’s only through a new job, the opportunities it has afforded, and the subsequent lifestyle creep, that I’ve recently come into possession of some truly nice ones, properly, properly nice ones I mean, and I’ll be dead honest it’s got me shifting just a little in my seat.

See, very nice clothes, especially very nice vintage reproductions, can be somewhat temperamental, especially when it comes to washing. Even if they’re often far more robust than a care label suggests (though that isn’t official advice— fuck around and find out at your own risk), I’m certainly feeling a little of that new car mindset, a desire to keep these things nice, even if that isn’t how you’re supposed to treat them. I find this to be sort of innate in having new clothes full stop, a struggle I wrote of some time ago. In essence, I’m much happier stepping into the stewardship of nice garms that someones else has broken in. I feel far less nervous about that, partly because they’re far cheaper, for sure, but also because all that initial creasing, washing, or roughening up is over and done with.

Good basics I find to be the hardest, since they get worn the hardest, washed the hardest, and more frequently. I’ve never had decent t-shirts on regular rotation till now, and it’s breaking my brain ever so slightly. I’m so used to these truly shitty white tees that can be blasted on high, fired through the dryer, as and when is necessary. I’m having to push the breaks hard, even if that isn’t the actual right move. My fear is that in endeavouring to keep these clothes nice I will fail to make them perfect, to allow them to soften and conform as these sorts of things can do. I’ve taken to exposure therapy just a little, the expensive sweatshirts are coming with me to play sports.

I have no doubt that there’s a point where this will feel “normal”, even as it remains positively abnormal, and it sort of goes without saying this is a minor thing. It’ll pass, but I think it matters. It’s the easiest thing to lose touch with where you started out, and so I’d like to place a flag here to remember what it was like, I can only assume I’ll continue down this path, it’s been the only dominant trend of my young adulthood. The alienation of newness is not just naïveté, I don’t think, it’s an unfamiliarity with the feeling of something, and it’s imposter syndrome. These are walls which as times can make the ultra niche world we move within feel like a fortress.


The ever underrated sweatshort

The sweatshort doesn’t get a whole lot of attention, they’re popular don’t get me wrong, but they tend not to be thrown into the shorts conversation in the way I think they ought to be. There aren’t a whole load of reproduction brands making them, so I’ve dug a few options out.

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