Fashion

Time Has Come for the Penny—Luckily, the Penny Loafer Remains

November 14, 2025

Photographed by Phil Oh

It’s official: The penny is on its way out. After 232 years, they’re cancelling it, literally. It matters little that they cost three times as much to mint, or that few of us still keep single cents in our wallets—in our heart of hearts, they’ll always belong on the vamp of a great loafer, even after they disappear from circulation.

Vogue’s Favorite Penny Loafers

Image may contain: Clothing, Footwear, Shoe, and Sneaker
The Original Icon

G.H. Bass Weejuns penny loafers

Jump to review

$175

NORDSTROM

The Under-$300 Find

Banana Republic penny loafers

Jump to review

$240

BANANA REPUBLIC

The Suede Style

Veronica Beard penny loafers

Jump to review

$395

NORDSTROM

The penny loafer has been a fixture of American style since the 1930s, when G.H. Bass introduced the “Weejun,” a Scandinavian-inspired slip-on with a tidy little slot just big enough for a coin. Students slipped in pennies for good luck and a cultural icon was born. Penny loafers eventually came to define everything from Ivy League dressing to ’90s minimalism.

Nearly a century later, the shoe’s appeal is broader than ever. The best loafers for women are a true wardrobe workhorse: genderless, ageless, and endlessly adaptable. Fashion insiders wear them with puddled trousers and oversized knits; celebrities sport them year-round with jeans and knits, and preps still swear by a traditional black or oxblood pair that goes with everything.

Part of the loafer’s magic is its range. It can skew crisp and collegiate or subversively cool, polished enough for the office yet relaxed enough for weekend errands. The best penny loafers for women make an excellent anchor for tailoring, dresses, stiff denim, or slouchy layers.

If the demise of the penny has you feeling sentimental, or maybe even a little shortchanged, consider this your excuse to revisit the timeless style it helped make famous. You might need to look elsewhere for a little luck, but as far as penny loafers go, the below are worth every cent.

In for a Penny, in for a Pound

The classic penny loafer, of course, looks great with other staples like a bomber jacket, jeans, and button-ups.

Saint Laurent

bomber jacket

$700

SAINT LAURENT

Alex Mill

Jo shirt

$195

ALEX MILL

Levi’s

501 ’90s jeans

$98

LEVI’S

Uniqlo

Heattech scarf

$25

UNIQLO

Elisa Johnson

Jane metal sunglasses

$145

SHOPBOP

Burberry

leather cadet loafers

$920

NORDSTROM

A Pretty Penny

For a cheeky yet mature take on the school-girl skirt and shoes, wear a pleated skirt that hits mid-calf with Miu Miu’s heeled loafers. A suede jacket and a turtleneck take the outfit into fall.

Banana Republic

heritage suede jacket

$598

BANANA REPUBLIC

Everlane

The Cloud turtleneck

$188

EVERLANE

Gabriela Hearst

Wesley midi skirt

$1,350

NET-A-PORTER

Miu Miu

penny loafer

$1,220

NORDSTROM

Coach

Hamptons hobo bag

$295

COACH

Éterne

rib socks

$21

FWRD

See a Penny, Pick it Up

Timeless with a preppy twist: mix suiting separates with a plaid button-up and black leather penny loafers.

The Row

Eudora blazer

$3,100

NET-A-PORTER

Cos

flannel shirt

$149

COS

The Row

Virgil wide-leg pants

$1,350

NET-A-PORTER

Image may contain: Clothing, Footwear, Shoe, and Sneaker

G.H. Bass

Weejuns penny loafers

$175

NORDSTROM

Ana Luisa

Eden hoops

$65

ANA LUISA

Anderson’s

textured-leather belt

$270

NET-A-PORTER

A Penny for Your Thoughts

Rich burgundy loafers pair well with cozy textured clothes, like a knit dress, chunky socks, and a lush camel topper.

Toteme

draped coat

$1,490

NET-A-PORTER

The Elder Statesman

Tranquility maxi dress

$1,795

NET-A-PORTER

Uniqlo

Heattech slouchy socks

$8

UNIQLO

Mansur Gavriel

penny loafers

$545

NORDSTROM

Sophie Buhai

droplet earrings

$475

NET-A-PORTER

Métier

Chameleon 41 tote

$2,650

NET-A-PORTER

When the Penny Drops

Mix a hint of collegiate charm with cool off-duty separates (track pants, hoodie, cap) for a balanced take on high-low dressing.

Burberry

Fitzrovia trench coat

$3,150

BURBERRY

Acne Studios

printed hoodie

$620

NET-A-PORTER

Wales Bonner

Mantra track pants

$690

NET-A-PORTER

Prada

colorblock loafers

$1,220

NORDSTROM

Nike

unstructured hat

$25

NIKE

J.Crew

trouser socks

$60

J.CREW

Shop more penny loafers:

Loewe

Campo penny loafers

$1,400

NET-A-PORTER

Sesa New York

loafers

$345

ALEX MILL

Margaux

The Marlowe loafers

$385

MARGAUX

Zara

soft ruched loafers

$60

ZARA

Jamie Haller

The Penny loafers

$595

SHOPBOP

Tory Burch

heeled lug loafers

$450

SHOPBOP

Madewell

Porto penny loafers

$178

SHOPBOP

Frēda Salvador

Elba loafers

$378

SHOPBOP

J.Crew

Winona penny loafers

$228

J.CREW

Church’s

Pembrey loafers

$1,100

NET-A-PORTER

Veronica Beard

penny loafers

$395

NORDSTROM

Banana Republic

penny loafers

$240

BANANA REPUBLIC