Esquire USA - 03.2020

IT WAS A SATURDAY AFTERNOON IN
mid-December when I finally embraced it.
Staring into a full-length mirror, examining
the suit I’d just put on, I put my hands in
my pockets—and I couldn’t see the outline
of my knuckles. The gravestone would read
HERE LIE HIS SLIM PANTS, 2011–2019, but
the death warrant was written a while ago.
It took this moment to have the epiphany,
but the truth is that I’d been thinking about
moving on to more generously cut trousers
for the better part of two years. This was the
first time I’d felt good in a pair, but I was stand-
ing well on the latter side of their comeback.
Fuller silhouettes have been creeping their
way back into the zeitgeist over the past half
decade. Now, visible kneecaps and the out-
line of your six-and-a-half-inch iPhone 11 Pro
Max are being rapidly traded for clean,
straight lines, roomy interiors, and the abil-
ity to bend down and pick up your child with-
out literally bursting at the seams. My
aforementioned suit pants weren’t exactly
on the cutting edge of the movement, but get-
ting over the hump only put me into a better
position to indulge in an aspirational next
step: going high-waisted.
If finding a little breathing room for your
calves was an uphill battle, then pulling your
jawns up to your belly button might feel like
scaling a rock wall with your hands tied behind
your back. Worry not; with the right weapon—
like these at left from Michael Kors—you’ll be
comfortably equipped with a look that will
make both your grandfather and your cool
Parisian friend point their cigarette at you in
approval. When the pants go up, your silhou-
ette streamlines, ridding your mind of that lit-
tle whisper of JNCO that sets in when you first
read the word baggy (or, perhaps, wide leg).
Once you’re working with the right trou-
sers, finish off your look by keeping the rest
simple. The best way to ease into this type of
styling is with a well-fitting, tucked-in T-shirt
and a jacket that’s long enough to balance the
whole thing out. This isn’t an arena where you
want to go wild with pattern mixing, but if the
trousers are solid and the tee is minimal, a
jacket with some texture can add the just-right
amount of attitude.
It’s an advanced move, for sure, but one
that spans the decades. Cary Grant did it in
the ’40s and Harry Styles did it in his recent
Saturday Night Live hosting gig. Hell, even
Connery’s Bond hiked ’em up in Dr. No. Ye s ,
it will feel odd at first. Yes, strangers will do
a double take. But anyone who wore skinny
jeans before 2005 knows that feeling. And
they’ll feel it again in the late 2030s, when
we’re talking about that comeback, too.

“

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CONTEXT-FREE QUOTE FROM A BOOK WE LOVE

—BRANDON TAYLOR,

REAL LIFE

(OUT FEBRUARY 18)

Study these celebrity looks from high-waisted

history to inspire your next move

Way back in November ’19,

HARRY STYLES followed suit

while hosting SNL draped

in an exact look from the Gucci

Spring 2020 runway.

SEAN CONNERY wears ’em high

in 1962’s Dr. No, proving this

tactic is well deployed

when going monochromatic.

DAPPER DAN is no stranger

to extreme fits. The legend went

way wide and way high in

a look that’s tailor-made for his

energy: big.

The move still plays if you’re not

tucked in, as CARY GRANT

displays with his sweater-over-

trousers look.

TROUSERS ($790) BY MICHAEL KORS
COLLECTION; T-SHIRT ($88) BY LEVI’S VINTAGE
CLOTHING; SHOES BY O’KEEFFE.

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