Preppy is a word that makes the average fashionista flinch. It’s those
associations: bankers in seersucker jackets; public-school boys running riot
in Rock in stick-up-collared polo shirts; girls who would kill to be at the
same polo match as Prince Harry, in their uniform of pale-pink hoodies and
denim miniskirts, accessorised with blonde hair and ankle Uggs. It’s Sloane
rangers. It’s sporty, county, gap-year and it’s been about as far as you can
get from the cutting edge of style. Yet rapidly growing numbers of people
are embracing the preppy look — whether it’s stripy boat-neck T-shirts,
argyle sweaters, brogues or cotton pea coats. Look closely and you’ll see
preppy is having a makeover right under our noses.
It’s still the default look of every Sophie and Hugo on the planet (Jack
Wills, provider of the logo-heavy collegiate wear that is their unofficial
uniform, saw a sales increase of 100% last year). But the difference is
that, now, all kinds of other style tribes are cherry-picking from the
preppy canon — that mixture of American sporty casual wear from shops such
as Abercrombie & Fitch and British old-school classics — and wearing it
in new ways. When types you would never have dreamt of labelling preppy
(Alexa Chung, say) start wearing clothes you definitely think of as preppy
(cardigans, blazers, penny loafers, ankle socks), you are talking about a
wholesale rebranding.
As to why preppy suddenly has such a broad appeal, that’s easy. It’s the
antibling look — clean and classic to the core. So, naturally, it’s heading
mainstream at the same time as we are tiring of
Wags and multi bags and the excesses of the red carpet. It’s easy to pull off
preppy without having to invest much. Tick. It’s uncomplicated and eminently
wearable, requiring no inside fashion knowledge or clever styling. Another
tick. And preppy doesn’t date. Blazers and pea coats and stripy shirts exist
in their own fashion limbo for all time. Double tick.
Preppy has something else going for it. There is an extended line of wholesome
preppy-wearers, from Katharine Hepburn all the way to the present day, that
gives it a kind of authenticity that speaks to a generation bored with
gimmickry and clothes that last only a month or a wash. Preppy is the
antithesis of trashy. Like a cashmere jumper borrowed from Dad, it has a
whiff of permanence. In the end, this is about a shift away from the fickle
diktats of fashion to the appeal of stuff that feels like it belongs in real
life, not merely on a catwalk. You can see why it’s catching on.
This is the Jack Wills posse. Younger ones wear a hoodie and denim miniskirt.
Older, grungier sisters wear a cotton checked shirt as a dress, saggy
cardigan, black opaque tights and rolled-down Ugg boots. Note the roughed-up
hair (though beautifully conditioned), the bitten, painted nails and the
faded tattoo (she got it travelling).
POWER PREPPY
The grown-up, glamour end of preppy. It’s preppy with an injection of
designer, and you won’t see any logos anywhere. Classic looks include a dark
jacket with a white shirt and bootcut denim for smart-casual, and, for
casual, sawn-off long white denim shorts, a vest and a pashmina.
Poster girls Michelle Obama, Jennifer Aniston, or, if you like your
preppy a bit LA, Elle Macpherson.
Defining elements The juicy-coloured statement cardigan, white shirt,
capri pants, white jeans.
Favourite labels J Crew, Gap, Boden for downtime (must be worn with a
lot of care), Derek Lam for designer.
Most likely to be seen wearing them At home, on holiday, at the
weekend, on the school run.
Best look Crisp shirt with ankle-grazer jeans and ballet pumps;
bright-coloured cardigan with full skirt.
A look too far Madras checked jackets for men, seersucker trousers and
canvas belts featuring ducks, bermuda shorts.
PUBLIC-SCHOOL PREPPY
Poster people Prince Harry, Chelsy Davy.
Defining elements Uggs (still, even in summer) or white canvas
plimsolls, the gratuitous scarf (this year in cotton plaid).
Favourite labels Jack Wills, Gap, Crew Clothing.
Most likely to be seen wearing them In gangs on the King’s Road, Rock,
Polzeath, Aldeburgh, the northeast coast of Corfu, traipsing round John
Lewis with their mothers.
Best look Denim shorts and pretty chemisey top with ribbed cotton
tights and white plimsolls.
A look too far Upturned collars or rugby shirts on girls or boys,
low-riding jeans with stripy boxers on show, cricket sweaters (unless you
are playing cricket).
FASHION PREPPY
This is doing the look with irony, which means taking the most traditional of
preppy signatures — penny loafers, ankle socks, Aertex shirts with logos,
stripy men’s shirts, wax jackets, hair bands, Hunters, heirloom brooches —
and wearing them as a preppy never would. Alexa Chung puts loafers with
minidresses, and wellies with denim shorts; Chloë Sevigny likes a blazer
over hot pants, or a neat pair of khaki shorts and a boob tube.
Poster girls Alexa Chung, Chloë Sevigny
Defining elements Vintage sundresses, knee and ankle socks, brogues,
loafers, two-tone pumps.
Favourite labels Anything vintage, Luella, Marc Jacobs, American
Apparel for sweatshirts.
Most likely to be seen wearing them When you’d least expect. At a
black-tie party, rock festival, their best friend’s wedding.
Best look Loafers with knee socks and a super-mini designer dress.
A look too far Hunters in town (note, fashion preppy knows to keep hers
for Glastonbury), head-to-toe Belstaff.
PIT-BULL PREPPY
This is a pimped-up version of Public School Preppy, with, possibly, a pit
bull on a designer lead. Pit-bull preppy has picked up where the designer
tracksuit left off. It’s big on sporty signature looks (hoodies, baseball
caps), but not so big on the wholesome aesthetic, or the sports.
Poster people Danny Cipriani for the boys (it’s all those sweatshirts
teamed with diamond earrings), and the chicks from The Hills or Katie Price
in equestrian mode for the girls. Think soft-top sports car meets sportswear
or Page Three meets pony club.
Defining elements White track pants, white gilets, Uggs, nail
extensions and ponytail.
Favourite labels Jack Wills, Topshop, Asos, H&M.
Most likely to be seen wearing them On the high street.
Best look Rolled-down track pants and padded gilet with nothing
underneath.
A look too far Thong riding up above the waistband of trackie bottoms.
EURO PREPPY
Euro preppies are the only people wearing the look precisely as the original
Sloane rangers used to: sans irony. Only, of course, they are 10 times more
polished, and whereas the original Sloane might have been covered in jack
russell hairs and barely-there make-up, your Euro preppy is immaculate,
wears only cashmere and is allergic to animals.
Poster girls Carla Bruni, with her cable-knit cashmere and loafers;
Kate Middleton, with her Spanish riding boots and tweedy shooting kit. (To
be fair, Kate is more neo-Sloane ranger, but, for obvious reasons, the Euro
preppy holds her in high esteem.)
Defining elements Cable-knit cashmere in pastel colours, velvet
scrunchies, riding boots worn over jeans.
Favourite labels Barbour, Hackett, Thomas Pink.
Most likely to be seen wearing them All the time, head to toe, all over
Europe and South Kensington.
Best look Stripy shirt under a fitted tweed jacket, and lots of rings.
A look too far Designer riding clothes as mufti.
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