Updated June 2021
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Buying guide for best stilettos

Does your shoe collection include a pair of stilettos? Stilettos aren’t just any pair of heels — they’re in a league of their own. Not only do they add height and elevate your look, they inspire confidence with every step.

Stilettos stand out with their long, slender heels that elegantly reposition feet to elongate and accentuate legs. Whether you prefer a shiny, patent leather finish or a strappy open-toed design, one thing is for sure: stilettos make a statement. In fact, you even carry yourself differently in them, in more than one way. Given their design, stilettos require better posture and encourage you to stand up straight to maintain an even, comfortable stride. With these small adjustments, your body language also changes for the better, presenting you as a confident, assertive individual.

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If you’re comfortable in a specific pair of stilettos, consider getting them in more than one color or finish to match multiple outfits in your wardrobe.

Key considerations

What are stilettos?

If you’re looking for an official definition of stiletto, you’ll be hard-pressed to find it. While most people and shoe manufacturers agree the signature feature of stilettos is a long, tapering heel, that’s all they’ll agree on. 

Some parties say a stiletto should be no shorter than 3.5 inches, whereas others say any pair with a pointy, tapered heel shape counts as a stiletto. High-heel traditionalists insist stilettos are distinctly different from platform heels, and a true stiletto won’t be platform at all. Certain fashion experts go so far as to say stilettos are only closed-toed, because open-toed varieties are simply classified as high-heeled sandals. Basically, stilettos remain a hotly debated topic in the world of fashion.

Comfort level

Given their sky-high design, stilettos, like all high heels, lack the conventional comfort of flat footwear. It comes as no surprise that wearing stilettos changes your foot position during wear. This can result in sore toes and aching heels, and in some cases, blisters or calluses. The fact is even stiletto heels with moderate cushioning and comfort features can be painful to wear for prolonged periods of time. It also depends on the person, because some people won’t experience as much discomfort as others. 

With that said, many stiletto lovers simply opt to minimize their wear time. If you’re attending a wedding in stilettos, for example, wear flat shoes in transit and only change into your stilettos once you arrive at the venue. It goes without saying that plenty of women forgo their heels to hit the dance floor at some point in the night. 

Anatomy of a stiletto

Heel: The stiletto heel can be made from any combination of plastic, wood, leather, bamboo, or rubber. Some heels also have an inner metal rod for stabilization. At the bottom of the stiletto is the heel tip, also called a heel lift. This small rubber or plastic piece is what comes in contact with the ground and, to some degree, absorbs shock. 

Toe: The toe of a stiletto is usually pointed and exaggerated and helps elongate the profile of the shoe as well as your legs. This makes the toe box area, which covers your toes through the tip of the shoe, remarkably narrow. If you have wider feet, you may experience crushed toes in stilettos if you don’t opt for a wide width. 

Outsole: The outsole refers to the outermost materials of the sole. These are made from rubber, leather, or a blend of synthetic materials. The outsole is what comes in contact with the ground, and, like the heel tip, absorbs shock. Thinner outsoles are less effective at this because there simply aren’t enough layers. Stilettos with thicker outsoles tend to do a better job of softening contact with the ground, but they can give some designs a slightly chunky or bulky appearance. 

Insole: If you would like to have some semblance of comfort while wearing stilettos, aim for a pair with a cushioned insole. These have gel or memory foam that contours to your foot to provide additional support and shock absorption. If you fall in love with a pair that has a thin insole, don’t fret. This frees up considerable room inside the stilettos to add your own cushioned insoles, some of which are specially made to fit inside high-heeled shoes. 

Upper: The exterior materials of stilettos introduce texture and dimension to the overall design. The upper can be made of leather, suede, vegan leather, satin, cotton, denim, and any other material you can imagine. Certain materials are more breathable than others, such as leather and cotton, and your feet may sweat less inside them. Synthetic materials, on the other hand, aren’t necessarily porous, so your feet are more likely to sweat or swell while wearing them. 

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Be mindful of where you intend to wear your stilettos, because the ground and weather may damage your beloved heels. Outdoor weddings in grass can damage the heel, while wet or snowy weather can saturate or stain fabric or suede.


Cushioned insoles: Dr. Scholl’s High Heel Relief Insoles
Minimize discomfort in your stilettos with these gel insoles by Dr. Scholl’s. They provide targeted cushioning through arch and heel support. 

Heel protectors: GoGoHeel Stoppers Heel Protectors
Prevent your stiletto heels from sustaining damage and sinking in soft ground with these heel protectors. They’re clear and barely noticeable, plus they’re easy to pop on and off your stilettos. 

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Expert Tip
When packing your stilettos in a suitcase, consider wrapping them in soft garments. This will prevent them from bumping into the hard edges of your suitcase or sustaining damage from surrounding items.

Stiletto prices

When it comes to stilettos, you can spend anywhere from $25 to $1,000. Materials and quality drive the price, though with some stilettos the high price comes from having an iconic designer name.

Inexpensive: You can invest in budget-friendly stiletto heels for $25 to $50. These are usually made with synthetic materials and rarely come with cushioned insoles.

Mid-range: As you enter the $50 to $200 range, you’ll find a wide variety of well-made stilettos featuring leather materials, as well as embellished designs.

Expensive: If you’re in the market for a designer pair of stilettos, be prepared to spend between $300 and $1,000. These are stylish and iconic, but make sure you’re ready to care for them with the right shoe-cleaning products to protect your investment. 

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Did you know?
While most stilettos are available in women’s U.S. sizes 6 through 11, it can be more challenging to find sizes outside this range. You may need to contact the manufacturer to see if the shoes are available for direct purchase.


  • Pay attention to the finish. Stilettos are stylish and classy, and their finish impacts your overall look. If you prefer a subtler, more conservative look, aim for matte leather stilettos. If you’re looking for a pair to dress up your look, choose patent leather.

  • Avoid driving in stilettos. While it’s convenient to get in and out of cars without changing shoes, it’s recommended that you not drive in stilettos. Given the pressure on your heels as you use the pedals, you could break the heel.

  • Keep the box or invest in a shoe rack. Stilettos might not be worn as often as other footwear, so make sure you store them appropriately. They’ll avoid dents, crushing, and scratches if they’re kept in their original box or placed on a shoe rack

  • Go bold. If you normally wear neutral or plain stilettos, invest in one pair with a bold color or print. They’ll be the perfect way to introduce a bit of style and pizzazz to monochromatic or simple outfits.

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If you spend big bucks on pedicures, keep in mind that tight-fitting stilettos may damage or chip the polish.


Q. I haven’t worn my leather stilettos in a while, and now they feel dry. What happened?
A. There’s a bit of maintenance required when it comes to leather footwear and accessories. When storing them between uses, make sure they’re in a breathable, climate-controlled location. It’s also important to clean and care for them with the right products. To keep leather moisturized and crack-free, it’s a good idea to apply leather conditioner to them a few times a year.

Q. It looks like the soles of my stilettos are completely worn out. Do I need to buy new ones?
A. Not necessarily, especially if the rest of the shoe is in good condition. Instead, take your stilettos to a leather tailor or cobbler to resole and repair them. The price can vary, but in some cases, it ends up being less expensive to pay for the service than to replace the stilettos.

Q. Should I invest in stilettos with or without ankle straps?
A. An ankle strap is a good idea to provide additional support, plus you don’t need to worry about the back of the stiletto slipping off your heel. If you have shorter legs, however, ankle straps can cut off your profile, making your legs look even shorter. 

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