Styling a Nineties Slingback in New York

Why Heels Matter Now

Vintage heels were built by people who expected them to be resoled. The lasts are narrower, the leather is thicker, and a nineties block heel is far more walkable than anything designed for a photograph. In 1995, when a woman in Manhattan hailed a cab, she did not kick off her shoes first. She stepped off the curb in a heel that had to survive a subway grate, a puddle, and a flight of stairs. That engineering is why a vintage heel still feels different on your foot. The toe box has room for your actual toes. The arch sits where your arch sits. And the heel itself is weighted like a pendulum, not a stiletto nail.

You do not have time to ruminate. You see the shoe, you check the sole, you pay, you walk out. But you also need to know what you are looking at. Because a vintage heel is not a costume. It is a piece of construction that can carry you from a meeting in Midtown to a drink in the East Village, if you choose it right.

How to Wear It

Skip the formal styling. A slingback with raw-hem denim is the modern way. The nineties themselves were the era of slip dresses and combat boots, so you are not doing something foreign. You are doing something familiar with a heel that has a little history. Take a pair of black leather slingbacks, the kind that closed the decade, and wear them with jeans that are cut straight and end an inch above the ankle. Let the heel be the only polished thing. A white t-shirt, a blazer, and that shoe is a New York uniform.

Pair a sculptural heel with a plain slip dress and let the shoe carry it. A 1997 Prada-inspired platform with a chunky heel, or a simple mule with a curved block, does not need a pattern or a print. The dress is a canvas. The shoe is the art. I once wore a pair of early-nineties Charles Jourdan slingbacks with a black slip dress to a gallery opening in Chelsea. The dress cost forty dollars. The shoes cost a hundred and forty. Everyone asked about the shoes.

A Mary Jane with a white sock is still one of the best cheap tricks in fashion. It is a look that reads as both innocent and knowing, and it works with a miniskirt, a midi dress, or cropped trousers. The sock should be ankle-length, not crew. The shoe should be a solid color, not patent. And you should commit. Half-hearted Mary Jane styling is just a schoolgirl costume. Full-hearted is a statement.

Where to Find Yours in New York

• L Train Vintage (204 Bedford Avenue, Brooklyn) — volume shopping, low prices, be thorough, from around 20 euros. This place is a warehouse of near-misses. You will rifle through racks of men’s flannels and faded Levi’s to find a pair of heeled loafers from 1994. But they are there, and they are cheap. Do not go with a hangover. Go with time.
• What Goes Around Comes Around (351 West Broadway) — the grail room, priced accordingly, from around 45 euros. This is where you go when you want a specific thing: a YSL Tribute, a Chanel slingback from the ’80s, a pair of Martin Margiela Tabi boots that still have their box. The staff knows what they have. The prices reflect it. But sometimes you need the grail, and this is the place to find it.
• Beacon's Closet (74 Guernsey Street, Brooklyn) — resale done properly, good turnover, from around 60 euros. Beacon’s is a step up from L Train in curation and price. The shoes are organized by color, which is both a blessing and a curse. You will find a pair of Manolo Blahniks next to a pair of Nine West. Check every pair. The good ones hide.
• Chelsea Flea Market (West 25th Street) — weekends, bring cash and haggle politely, from around 90 euros. The flea market is a different beast. You are dealing with dealers who know what they have but are willing to negotiate if you are serious. Bring cash. A hundred dollars in small bills gets you a better price than a credit card. And do not be afraid to walk away. There is always another pair next weekend.

Go on a weekday morning if you can. The rails are fullest before the weekend crowd arrives, and staff have time to show you what came in overnight. On a Tuesday at 10 a.m., you can take your time. You can try on four pairs and decide that none of them are right. The pressure of a Saturday crowd is not your friend. You will buy something you do not need, and you will regret it by Sunday.

What to Look For

Turn them over first. A replaceable heel tip and a stitched, not glued, sole mean a shoe worth keeping. The heel tip is a small plastic or rubber cap at the bottom of the heel. If it is worn down, that is fine. A cobbler can replace it for ten dollars. But if the heel itself is cracked, or the sole is coming away from the leather in sheets, you are looking at a repair bill that is not worth it. Stitched soles are the mark of a good shoe. Glued soles are the mark of a fast-fashion casualty. You want the former.

Check the insole for a maker's stamp. A name like Charles Jourdan, Bally, or Ferragamo tells you something about the construction. It means the shoe was made with a last that was designed for a real foot, not a generic shape. It means the leather was cut from a good part of the hide. It means the heel was balanced to a millimeter. If there is no stamp, look at the stitching. Even stitching, tight and even, is a good sign. Loose threads are a warning.

Check the heel for wobble. Hold the shoe in both hands and gently twist the heel. If it moves, it is not stable. A heel that wobbles on the shelf will wobble on the street, and you will break an ankle. Some wobble is caused by a loose heel nail, which a cobbler can fix. But if the heel is cracked, do not buy it. You cannot fix a cracked heel.

Scuffed leather polishes out beautifully; cracked leather across the toe box does not, no matter what anyone tells you. A scuff is a surface mark. A crack is a structural failure. You can buff a scuff with a little polish and a soft cloth. You can even hide a crack with a matching cream, but the crack will open up again the first time you bend your foot. Do not let a seller convince you otherwise. They are trying to move inventory, not save your soles.

One last thing: try it on properly, walk around in it, and sit down. A pair of vintage heels that only works standing still is not going to survive your actual life. You will have to walk to the subway. You will have to stand in a line. You will have to sit at a bar and cross your legs. The shoe has to move with you. If it pinches in the store, it will pinch on the street. If it slips at the heel, it will slip all day. Do not buy a shoe that needs breaking in. Vintage shoes are already broken in by someone else. They should fit like a handshake, not a promise.

A pair of vintage heels is not a collectible. It is a tool. It is a piece of engineering that has outlasted its original owner, and it will outlast you if you treat it right. So go find yours. Go on a Tuesday. Bring cash. Turn it over. Walk in it. And when you walk out, you will have a shoe that has seen New York before, and is ready to see it again.