As Time Goes By

Invest in timeless, classic styles of well-made shoes and you’ll always be in fashion.

The Penny Loafer

Alden’s style No. 986, in cordovan ($480); from Leather Soul.
Photographed by: Rae Huo
Styled by: Lori Anne Tomonari and Kathryn Drury Wagner

"The ultimate American shoe is a penny loafer. You can wear them with slacks and an aloha shirt, or with khakis," says Park. But not with a suit, as cordovan, a dark, wine-colored leather, is considered too casual for that use.

The Oxford

The Hancock, by Allen Edmonds ($294), from Nordstrom.


"You’d see these even in the 1940s, and you can tell it’s a classic, because pretty much every brand of shoe makes an Oxford," says Tom Park. "Every guy should have at least one pair of these."

The Wingtip

The Malvern style ($825), by Edward Green, from Leather Soul.

"A power shoe, the kind that walks down Wall Street," observes Park. Gillian Armour, an image consultant based downtown, adds, "These stylish, formal business shoes come to us via Ireland and Scotland, where they once were heelless hunting shoes. The reinforced, perforated bindings on the sides allowed the water of the boggy soils to drain out of the shoe as the wearer waded about."

The Driving Moccasin

From the "Ferrari" collection. ($425), by Tod’s.

Sure, these shoes are very European, but even if you’re not zipping around on the back of a Vespa in Rome, pebble-bottom driving shoes are comfortable and look put-together. A classic is the chocolate brown, but they come in all hues, like this red

The Boat Shoe

Sperry Top-Sider ($54.99), in Sahara color, from the West Marine store.

Sailors have long known that a pair of oil-tanned leather moccasins offers good grip and a relaxed style. Pam Chambers, a presentation coach, recommends this look to clients for casual wear, such as use on casual Fridays.


The Pump

Manolo Blahnik pump, Tuccio ($495), from Neiman Marcus.

"This shoe style flatters every leg," says Armour. "It’s a favorite of women, because it makes the wearer that much taller and the legs longer. It’s an absolute necessity for any fashionista’s wardrobe. A black pair will see you through many glamorous days."

Spectator Pump

Carisa style ($280), in magnolia/black, from Salvatore Ferragamo.

"It’s a throwback classic that goes back to the 1930s: a two-tone combination of shoe and spats," says Armour. Spectators have traditionally been considered a spring/summer shoe.

Evening Shoe

Concorde style ($840), in ecru satin, by Louis Vuitton.

Every woman needs a glam pair of evening shoes. With many styles being backless or open-toed, Chambers points out that "a pedicure is a must." She adds that "hosiery should not be worn with open-toed shoes."

Ballet Flat

Ashley flat, in bronze ($98), from Banana Republic.

"The darling of Audrey Hepburn’s feet and the reason her posture was so perfect," says Armour. "One can stand tall in comfortable flat shoes forever."

T-Strap Sandal

V-Gamba ($145), by Via Spiga, from Macy’s.

The oldest surviving sandals are exhibited in the British Museum and date to 1500 B.C., yet sandals have changed little since antiquity. Different cultures do, however, prefer the thong on different toes. The ancient Greeks used their big toes to secure their sandals.

Shoe Care

AA Start smart. After you buy a pair of shoes, prep them before you wear them, applying a leather cream or conditioner. "It seals out water and protects the leather from cracking. It keeps the shoe young," says Bob LoPresti, a third-generation cobbler and president of Joe Pacific Shoe Repair. "And on the really high-end shoes, put a sole guard on the shoe right away," he urges, pointing to a pair of new, incredibly thinly soled Gucci heels.

AA Don’t wear the same pair of shoes every day-give them a break to let them air out and fully dry. If they look dusty, give them a quick brush before storing them back in your closet.


AA Speaking of brushes, brush off suede shoes several times a season. It will help them last longer.

AA "The most important thing to the care of shoes is the shoe tree, says Tom Park, who adds, "Rochester Shoe Tree is the best brand for the money." Shoe trees can be plastic or wood, but wood is better, because it absorbs moisture. A shoe tree also keeps the shoe’s shape and stops creases from forming across the vamp, or front of the shoe. "If you don’t use shoe trees, the shoes will start to curl-and that leprechaun look is not a classic," says Pam Chambers. "Stuffing the toes with paper isn’t a good idea, as it makes the leather dry in a lumpy fashion."

AA Invest in a carpet pad for your car to put on the driver’s side floor. Driving can be hard on your shoes, particularly the back heel of the right shoe.

AA If leather shoes get wet, let them dry out on a shoe tree, then recondition them, suggests LoPresti.

AA If you’re not wearing socks and find that you are slipping around in your shoes, a particular problem in sandals, try a fabric insole. sells a good peel-and-stick version.

AA Once a week, polish leather shoes. "A basic shoe shine kit includes a polish, a brush and a soft cloth," says LoPresti.

AA "If you’re lucky enough to find a shoeshine guy, treat yourself," says Chambers, but, she warns that, "If we get in the habit of only having other people polishing our shoes, we aren’t polishing them enough."