O's Ultimate Shoe-Buying Guide

Oprah's Personal Pain-O-Meter
Forget organizing by color...Oprah organizes her shoes by how long she can bear to keep them on her feet.

Killer Shoes Don't Have to Kill
The shoe doctor is in to tell us precisely what makes a shoe (a good-looking shoe, mind you) safe and supportive. 

"Flip-Flops Are Comfortable"
...and more shoe lies we tell ourselves.

Shoe Crimes and Punishment
Four common foot problems—and how to avoid them.

A Podiatrist's Secret Weapon
Are expensive orthotics worth the money?

Even the sanest women can be shoe crazy—noticeably greedy and disturbingly vain about what they put on their feet. Given a choice between limping along in something really cool or running around in hideous "comfort" models, many of us would stick with crippled-and-gorgeous. But there's a third way: Jaleh Hoorfar, doctor of podiatric medicine, is enough like us to empathize—she loves high heels—yet she's trained to identify precisely what makes a shoe (a good-looking shoe, mind you) safe and supportive. Here's what she told us. (And if the pair you adore flunks a couple of her tests: Wear them, cherish them, just don't plan a five-mile walk in them.)

Sizes aren't standardized. An 8 from one designer may be a 7 or 8 from another (shoes made in Europe are usually narrower in front), so don't fixate on a number; always try on a half-size larger or smaller as well. To avoid buying shoes that are too tight, shop later in the day, when a bit of swelling is normal. And get remeasured yearly: Feet flatten and widen with age, pregnancy, and weight gain (if you slim down, your feet do, too).

Heavy shoes are suspect. They're just too much work to walk in: Your feet get tired and roll inward, leading to painful side effects.

Materials should be flexible. Patent leather is wildly popular this season, but tricky for shoes because it doesn't stretch to accommodate the foot (ditto for both plastic and fabric). Soft, high-quality leather or suede is ideal. Watch out for topstitching, which can reduce leather's elasticity.

Cushioning is key. Most feet are low in fat, so they need padding to be happy. Use thin gel inserts for greater comfort, particularly under the ball of the foot on high heels.

Mid-high heels make sense. Three inches is Hoorfar's limit. Not surprisingly, chunkier models are less inclined to wobble than the spindly kind (terrible for ankles). And your weight is better distributed if the shoe heel is centered under your heel, not placed too far back.

...And so do substantial soles. Ultrathin bottoms are torture, the doctor says: "There's nothing between your feet and the street." Luckily, some of today's hippest styles (wedges and platforms) have solid bottoms that act as shock absorbers. You can also ask your shoe repair guy to add rubber soles.

High-cut means lower risk. Shoes with sexy "toe cleavage" tend to rub against the foot at the widest point, where bunions form. A more covered toe casing is safer. Deep-dipping sides—or no sides—allow feet to slop over the edges instead of remaining properly aligned.

Adjustability is a plus. Look for laces, straps, or ties that can be loosened when the foot swells.

Flip-flops are so comfortable —they're almost like going barefoot. When toes have to grip to keep the shoe on, it causes tiny tears in the ligaments of the arch (a.k.a. plantar fasciitis). Hoorfar blames trendy thongs for the many cases of arch pain that walked through her door last summer.

Long, pointy toes are bad for you. Since the points are purely decorative—your feet don't reach that far into the shoe—they're no worse than round toes. The spot to beware the big squeeze is right below the toes, where your foot is widest and bunions develop.

Flats are easy on your feet. Not if they have no lift at all. A half- or one-inch heel gives necessary support (especially for flat feet with a tendency to roll inward) and prevents calf muscles from becoming overstretched and weak.

Shoes always feel tight at first —they'll stretch. Don't buy shoes that hurt, period. Even a professional stretching probably won't turn an uncomfortable pair into walking-on-air. (You can also try breaking in the shoes by wearing them around the house with thin socks for a few hours daily, but don't get your hopes up.)

To save suitcase space, travel with only one pair. Never wear the same shoes two days in a row, much less for an entire trip: It puts repeated pressure on identical areas of the foot, causing irritation and letting misalignment problems get entrenched.

The wrong shoes (too big, too small; too flimsy, stiff, or tall) are partly to blame for a host of foot problems. Switching to kinder, gentler styles is the first step toward relief. You can also ice, elevate, and take anti-inflammatories; in the longer run, orthotics—customized insoles prescribed by a podiatrist that realign the foot—may also help.

What a heel. Chronic stiletto wearers, who give the tendon at the back of their heels no chance to relax, often develop an inflammation known as Achilles tendinitis: There's an ouch every time the foot hits the ground.

Hitting a nerve. Cramming feet into narrow shoes can lead to neuromas, benign growths of nerve tissue between the third and fourth toes. The symptoms may be tingling and numbness in the ball of the foot or a sharp shooting pain.

A bumpy ride. Bunions are enlarged, misaligned big-toe joints: The bone at the toe's base protrudes outward instead of joining the toe bones, or phalanges, in a straight line. There may be a genetic component, but tight shoes are also a factor.

The hard stuff. The body's way of protecting itself against friction (such as that caused by too-small or too-big shoes) is to thicken the skin into calluses (on soles) and corns (on toes). Hoorfar warns against over-the-counter, acid-containing corn removers, which can "eat" healthy tissue.

Orthotics are customized insoles meant to realign the foot (change the angle at which it strikes the ground), making walking and running more efficient and taking pressure off painful areas. They're usually made by a lab from a plaster mold taken by a podiatrist, and come in different styles to fit into sneakers and dress shoes.

Although many podiatrists routinely recommend orthotics, their increasing use is controversial—especially since the cost (usually hundreds of dollars) is rarely covered by insurance. Robert Eckles, DPM, of the New York College of Podiatric Medicine, thinks orthotics are overprescribed for the general population. The appropriate medical strategy depends on the primary cause, he says: If malfunctioning feet are caused by overtraining or overweight, orthotics aren't going to fix that. Some practitioners also maintain that cheaper therapies—icing, stretching, less specialized shoe inserts—are as effective as prescription orthotics. Studies by Irene Davis, professor of physical therapy at the University of Delaware, found that "semi-custom" models (the lab uses a mold of the patient's feet to identify the best-fitting prefabricated insole) work as well as the totally customized, built-from-scratch kind.

Finicky Feet? If you're narrow, wide or somewhere in between, try these on for size