Women’s Stiletto Heel Tips That Work

There’s an old saying that doesn’t have to be true when it comes to wearing stilettos: “no pain, no gain”. While they’ll never be your first choice for a hike, stilettos don’t have to be uncomfortable, and there are some tips and tricks you can use to walk like a pro while not having sore feet or ankles afterward.  

There’s a reason high heels never seem to go out of style - they’re flattering, enhance your form, and add flair and sparkle to any outfit. If you’re attending a fancy event, there’s no doubt that many women there will be wearing heels - whether it’s stilettos, high heel boots, platforms, or more.

The comfort issues from high heels are due to the way they shift your center of balance, put pressure on the forward ball of your feet, and cause your body to shift forwards. However, you wouldn’t see those that depend on their physical fitness, like dancers, wearing heels regularly if there weren’t ways to overcome these issues. Stiletto heels are a staple of any fashionista’s wardrobe, so let’s take a look at some of these methods to keep you looking and feeling your best. 

With Enrico Cuini shoes our ALIA technology dissipates the forefoot pressure across the sole and transfer pressure back towards the heel. It also improves balance and energy return.

Stiletto Secrets

Getting the size right

A good general rule of thumb for stilettos is that they should be big enough for your largest foot, and long enough to comfortably fit your longest toe. They should never be too tight or too small, as this will lead to increased issues and less comfort. If your stilettos are too big, you can use insoles to pad them out, or if they are too small there are ways that shoe companies can stretch them out without damaging them.  At Enrico Cuini we recommend our heels to be made to your measurements.

If you are experiencing any of the following issues, your stilettos are likely not the right size:

  • They are too loose, and your heel can slide around in them

  • You struggle to get them on and your heel doesn’t seem to fit

  • Walking is consistently painful

  • You are getting blisters

  • Your toes don’t fit

  • Your heel is not centered directly over the stiletto

  • Your heel lifts out of the shoe when walking

  • The straps or ties are digging into your skin

Break them in

Like all new shoes, stilettos take some time to break in and become more comfortable and adjusted to our feet. What this means is that you don’t want to bring out a brand new pair of stilettos the night of a fancy event, you’ll want to get used to wearing them and stretch them out a little first. Try wearing them while relaxing at home, which will break them in while simultaneously allowing you to get more comfortable walking in them.  Good quality leather will stretch quite a bit so you want to buy stilettos especially pumps really snug at first to avoid having them too big down the line.

Stepping Properly

Heels require a slightly adjusted walk, due to their propensity to cause embarrassing slips and falls. When walking, remain conscious of how you are placing your feet - the correct way to walk in stilettos is heel-toe, where you place your heel down on the ground first, then roll onto your toes. While it may seem tricky at first, you will quickly get used to it. 

Proper posture

Heels cause certain parts of our body to lift, appearing younger, healthier, and more supple. This leads to an increased arch in the lower back, and an overall more forward posture. Over time, this can lead to issues, so try to correct it whenever you can.  

Keeping your chin level with the ground, head high, shoulders back, knees loose, and feet forward (not turned out) is the proper way to walk in heels. Not only will this lead to greater health and less back pain, it will also make you appear more confident and attractive as well.  

Replace the heel

If you are following all of the above tips and still experiencing issues or pain while wearing your heels, consider if it might be time to change out the stiletto. For pairs that are worn regularly, heels should be replaced roughly every 6 months to a year. They get worn down over time, and this could be leading to some issues. 

Use inserts

For shoes that you don’t want to replace or get rid of, but which are causing you pain while wearing, you can always try putting gel or cushion inserts in them. This will increase comfort and decrease lingering foot pain after taking them off. 


There have been many scientific studies done on the many ways that high heels literally make women appear more attractive to men. Some of it is subconscious, and some have to do with biomechanical markers like hip posture, but whatever the reason, one thing is certain - high heels aren’t going anywhere as a fashion staple. There are many good reasons to get used to wearing them comfortably, and many celebrities, athletes, dancers, and more can wear them regularly without any issues simply by following these tips and tricks.  

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What Are the Benefits of Wearing High Heels?

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How to Match High Heels and Stockings