From Jackie O to Rihanna, the Ultimate Guide to Classic Style

NOW IS the time to embrace the classics. OK, fine, it’s never not that time, but today, favoring such pieces over fleeting trends seems particularly prudent. “Trends are connected with timing and, in a way, time has stood still for the last year,” said New York fashion editor and author Tonne Goodman. “There’s comfort in knowing you have something that’s going to last.”

In the eyes of fashion folk, Ms. Goodman, 68—devoted to her uniform of white jeans, black turtlenecks and Charvet scarves—embodies classic style, even if that concept defies easy definition. Stylish types tend to deploy the term “classic” as capriciously as they do “chic” or “iconic.” It’s often (we think correctly) linked to Audrey Hepburn and LBDs but just as often (incorrectly) used to describe snootily preppy or stodgy garb. Technically, the word indicates something first-rate, of the highest class, representative of an ideal. Ms. Goodman reasoned that classic is not only a piece that’s practical and enduring that “you’ll wear forever,” but an attitude—it’s being comfortable in your clothes and skin. Here, 26 relatively indisputable examples of classic clothes, accessories and people.

A is for Alaïa Dress

From the 1980s until his 2017 death, couturier Azzedine Alaïa—beloved by supes like Stephanie Seymour (left)—crafted dresses that masterfully flattered the female form.

B is for Belgian Loafers

The leather loafers by New York institution Belgian Shoes are supple, not stuffy. Try them with jeans or fishnets, a la Kate Moss. $450, Belgian Shoes, 212-755-7372

C is for Chanel Tweed

Introduced by Coco in the early 20th century, the brand’s bouclé suits and jackets have variously stood for liberating androgyny and sexed-up irony.

D is for No-Stretch Denim

Elastic-infused jeans are just indigo leggings. No-stretch denim is crisper and closer to the genuine workwear article. $319, slvrlake-denim.com

E is for Equestrian

Horsey attire had fashion clout long before the Ralph Lauren label’s 1967 debut. These boots work well for the field and Fifth Avenue. From $1,485, vogelboots.com

F is for Borsalino Fedora

Humphrey Bogart, pretty much the personification of classic, was rarely seen without one of these Italian-made fedoras. Hat, $500, borsalino.com

G is for Geoffrey Beene

From the 1960s through the aughts, this American’s louche designs propelled the idea that an outfit should compliment the woman—not the other way around.

H is for Hoop Earrings

Sleek, simple hoops have endured for eons, adorning the ears of everyone from the ancient Romans to Meghan Markle. $325, sophiebuhai.com

I is for Intrecciato

Bottega Veneta’s woven leather is its signature. Memorably, Lauren Hutton carried a red Bottega Intrecciato clutch in 1980’s ‘American Gigolo.’ Bag, $3,100, bottegaveneta.com

J is for Jane Birkin

The epitome of effortless, Ms. Birkin’s confident, pared-back ’60s and ’70s looks are the stuff of style legend—which is why one of Hermès’s coveted bags bears her name.

K is for Kelly Bag

First released in the 1930s, this trapezoidal bag was allegedly renamed for the eminently elegant Grace Kelly after she carried it in the ’50s. $10,900, Hermès, 212-751-3181

L is for Leopard Print

This ferocious neutral earned classic status after

Christian Dior

used it in his 1947 New Look collection. Harris Wharf London Coat, $600, bloomingdales.com

M is for Manolo Maysale

These versatile kitten heels debuted on Isaac Mizrahi’s 1991 runway and have been wardrobe staples since. $745, manoloblahnik.com

N is for Navy and Black

They’re basically the same color, but not quite! This refined duo is a study in subtlety. Connolly Sweater, $379, matchesfashion.com; Skirt, $1,300, Celine, 212-535-3703

O is for the Olsens’ Oversized Style

Deliberate and cool, the baggy silhouettes the Row’s Mary-Kate and

Ashley Olsen

adopted in the 2000s still telegraph sophistication today.

P is for Pearls

Once seen as symbols of purity, pearls took on connotations of feminine rebellion thanks to Jazz-Age nonconformists like Josephine Baker, seen here in 1926.

Photo:

F. Martin Ramin/The Wall Street Journal

Q is for Quilting

How could an American pastime-turned-garment be anything but classic? This Bode jacket is comfort and tradition patched into one. $1,560, bodenewyork.com

R is for Rihanna Red

The ease with which RiRi wears her scarlet pout fuses old Hollywood panache with modern flair. Copy it with her Fenty-brand color. Lip Paint, $25, fentybeauty.com

S is for Charvet Silk Scarf

In quieter prints than their Hermés cousins, these scarves from a French brand beloved by royals are worn by those in the know. $360, Charvet, +33-1-42-60-30-70

T is for Tank Louis

A favorite since 1922, this version of Cartier’s recognizable, military tank-inspired watch has softer lines and smoother corners than other models. $10,200, cartier.com

U is for Understated

Whispering is infinitely more cultivated than screaming. Stand out by flying under the radar in unflashy neutrals like this pre-spring 2021 Totême ensemble.

V is for Verdura

Popularized by Coco Chanel and adored by Diana Vreeland, this brand’s gemstone-dappled accessories top jewelry fanatics’ wish lists. $97,500 each, Verdura, 212-758-3388

W is for White Jeans

A veritable blank slate, these trousers aren’t just for summer. Ms. Goodman pairs them with chelsea boots or velvet loafers in colder months. $245, frame-store.com

X is for X-ing One Accessory

Often attributed to Coco Chanel, the advice to nix one piece before leaving the house can make the difference between glam and gaudy.

Y is for YSL

In the 1960s and ’70s, Yves Saint Laurent gave us the subversive Le Smoking tuxedo, this mod Mondrian dress and legions of luxuriously rebellious bohemian looks.

Z is for Zero Waste

A classic is something you can wear for decades. Follow in Jackie O’s footsteps and eschew fast fashion in favor of pieces that will last a lifetime.

SEPARATE AND TOGETHER

One classic is great, but two is better. Here, timeless pairings for the fashion-history books.

Chanel Tweed + Denim

High/Low

Want to intimidate your fashion-obsessed pals by looking both devastatingly chic and totally nonchalant? Try this dichotomous combo. Dress the look up with a Manolo stiletto or down with a sneaker if you’re a true avant-garde iconoclast.

Intrecciato + Tank Louis

A Wrinkle in Time

Since joining Bottega Veneta in 2019, the brand’s 34-year-old creative director Daniel Lee has taken its signature braiding to new, edgy heights. Combining his textured clutch with this iconic (correct usage) Cartier timepiece is a style success that spans the ages.

Belgian Loafers + White Jeans

Below the Belt

If you don this shockingly sophisticated combination, it really does not matter what you wear on top. However, capping off this pairing with a boxy Chanel tweed jacket (see “C”) and a strand or two of statement pearls (see “P”) certainly wouldn’t hurt.

Quilting + Charvet Silk Scarf

American in Paris

Sure, at this moment in time, nonessential international travel is extremely ill-advised. However, combining Bode’s New World signature with Charvet’s silky European essential is just as thrilling (and far less expensive) as a first-class trip across the Atlantic.

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