This article is taken from the June 2021 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issue for just £10.

When I was a teen, you could look like a yob, a toff, or “alternative”. That was it. You paid your money, you made your choice. In masculine style terms, said options were represented as a trinity. There was George Michael, all Sun-Inned bouff, nicotine-orange tan, bleached denim and pastels.

There was Rupert Everett, he of the floppy fringe, patrician pallor, cheekbones and cricket whites. And there was Some Goth from The Cure: even bigger hair, green complexion, dank robes and badly-applied slap.

Flush with stripes, plaids, and Shetland sweaters, it speaks of British traditions in an American accent

As a middle-class girl from Birmingham, it was clear which brand of masculinity I would make my object. Yobs we had in spades. These were my classmates, my peers, the dubious-looking individuals who informed me I’d be almost attractive if I read less.

Goths abounded in our artsy provincial circles. Still, if I wanted neuroticism and heavy-handed kohl, I need only look in the mirror. No, it was the posho I craved. And if he could be an exquisitely tortured homosexual, then so much the better.

During my first Oxford summer, surrounded by the posh at play, I acquired a pair of penny loafers. I felt inauthentic in them, couldn’t quite make them work, but somehow seemed to require them.

Yet, I couldn’t really read them. And, the fact is, preppiness is confusing: a scruffy, anti-establishment guise in its Fifties heyday that now reads as snobbily smart because society got scruffier and more anti-establishment around it. Plus, it is meant to exclude; a uniform stringently policed while purporting to be relaxed.

Preppiness has its origins in the undergraduate guise that kicked off in Ivy League environs in the early twentieth century. If it is sporting in a Tom Buchanan kind of way — with its references to polo, sailing, and the like — it is dandyish in its pink-shirted Gatsbyish flourishes. Flush with stripes, plaids, and Shetland sweaters, it speaks of British traditions in an American accent, adding chinos, Bermuda shorts and Nantucket reds.

Female preppiness demands a play on mannishness, be it Katherine Hepburn Seven Sisters-esque in slacks, Ali McGraw as Love Story’s camel-coated manic pixie dream prole, or Diane Keaton as Manhattan’s Radcliffe heroine in her over-sized Ralph Lauren drag.

When US prep meets the UK, it acquires boarding-school, Sloane Ranger, and Brideshead aspects. When it runs across Euro chic, it is the BCBG (Bon Chic, Bon Genre) conservatism of the Parisian upper echelons.

Miuccia Prada once said that she knew little of American preppiness, “but I know perfectly the European equivalent of that look. I grew up in all of that and it was very much part of my education.”

The Bettses were Brummie bobo rather than BCBG. Still, flash forward thirty years, and I boast my own Eton mess to explain what is and isn’t U. Quoth the oracle: “The front of the loafer had to be stubby, not long, otherwise everyone would say: ‘You look like a dick,’ or ‘You pleb, Derbyshire’.

You could tell it was right if your heel perpetually came out of the shoe as you walked. This was further aided by the heel having been crushed by misuse. It also helped if your socks were school colours, preferably garishly striped and signalling some obscure sporting position such as Keeper of the Oppidan Wall.”

As a female of the species, I suggest taking the admonition to seek out stubbiness with a pinch of salt. Even Gucci’s girlish heeled loafers can make feet look trotter-ish. Instead, head straight to Bass for a pair of Weejuns, the original Ivy League loafer, with its slot for a penny for the pay phone.

Inspired by a Norwegian (hence “Weejuns”) farm shoe “for loafing in the fields”, the style was created in 1936, then discovered by an Esquire editor, who made it a must-have for the holiday-making elite. Grace Kelly, Audrey Hepburn, JFK, Steve McQueen, Paul Newman, and Michael Jackson, all wore them, in addition to contemporary style mavens Chloë Sevigny and Alexa Chung. So many Seven Sisters stalwarts were buying boys’ loafers that Bass designed women’s Weejuns. They come in an assortment of preppy hues — tan, navy, oxblood — but I can’t see why anyone wouldn’t want the black and white incarnation, which makes it so terribly hard not to tap dance (£130, www.ghbass-eu.com). Bloody comfortable.

I am rocking them to walk the hound with a bright blue striped Ralph Lauren button-down (£80, Zalando), striped tank top (£19.99, Zara), and my college cricket cap. These days, I am my own posh boy.