How to walk in high heels

Deep down inside, every girl wants to wear a pair of shoes that look like this:

Photo credit: The Sartorialist (c) 2011

There are a multitude of shoes out there that don’t hurt your feet, but you have to try them on. Limiting yourself to one type of shoe cuts down your choice of fashion altogether because some outfits require a higher shoe to work. Why short-change yourself? One needn’t turn an ankle to achieve a dashing silhouette, so I come bearing a little wisdom on how to get the job done. As a good blogger, I should caveat my advice with this: I am not a professional fashionista. I simply write from experience. If you want your first pair of heels to be six inches of craziness a la Lady Gaga, I don’t hold it against you, but I offer a warning. Been there, done that. Thankfully I wasn’t wearing leather chaps, though.


  1. Start small: As previously mentioned, you’re going to give up pretty soon after you strap on heels that are too high. Start with something that doesn’t strike the fear of god into your heart.
  2. Start thick: The thicker the heel, the more stable it is.

    Coned heels, which are very popular right now, are a great “starter heel”. It has the graceful look of a much thinner heel, but it’s stable enough that you won’t feel like you’re teetering.

    Square heels look chunky, but if you’re fashion-forward and adventurous, there are styles out there that can be worn. This Chloé sandal has a square heel that is slightly smaller than the shoe itself, making it look more delicate. Very stable, very chic.

    Kitten heels can be more unstable (avoid grates like the plague) but they’re the most delicate, and can be pretty comfortable. They vary in height and width, but anything under 2″ can be defined as a kitten heel.
  3. Build a tolerance. Your feet are muscular, and they must be trained to handle heels. By starting at a low, thicker heel you’re training your feet to handle your weight at an angle. If you run a marathon in the first get-go, you’re going to run out of breath very quickly. Training is necessary!
  4. Heel. Toe. When you’re walking, step with your heel, then your toe. Heel, toe. Heel, toe. See: The Simpsons, Season 4: “Lisa the Beauty Queen”.

  5. Buy well-made shoes. Well-made, not expensive. It’s true that expensive shoes are made from higher quality material, but that often just means you’re buying leather instead of polyurethane. Man-made material can be well-made as well. Check the glue, the stitching and the flexibility. Especially the flexibility! The more flexible a shoe, the more naturally it will move with your foot, the more comfortable it will be. Raphael Young recently applied for a flexible heels patent. You don’t need to shell out the big bucks for a flexible heel, just try them on!
  6. Use protection. Like everything on your body that comes in pairs, your feet are not identical. One foot may be wider than the other, toes might sit differently in shoes, you might even be a half size, or a full size smaller on one side! There are pads and liners you can purchase to help if you find your heel slipping out of pumps, or the ball of your feet need extra cushioning.
  7. Dress appropriately. Becoming a well-heeled woman (pun entirely intended) means learning to pair your footwear with your outfit as well as the occasion. If you’re on your feet for more than an hour, wear a sensible heel. More than three hours? I don’t advise wearing a heel at all. Catering staff never wear heels. Why? Because they have to move around quickly, efficiently and constantly. By all means, wear your highest heels to dinner or the theatre, you’ll be sitting for most of the evening anyway, but if you’re entertaining, keep your feet (and your lower back) in mind.
  8. Take chances. This piece of advice contradicts the one right above it, but I’m going to say it anyway: sometimes you should just take the chance. You might not know what the evening’s plans are, but if the outfit calls for something higher, go for it. You only live once, so why avoid looking fabulous?
  9. Come to terms with the fact that your feet will (sometimes) hurt. There is no magic cure. No shoe is perfect. Even flats can become unbearable, though. Over time you will find heels that you can wear for longer than a couple of minutes. You’ll find the style that suits you best and you’ll want to keep them for as long as possible. Get shoes reshod each season to extend longevity and you’ll be rocking your heels all year round.

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2 thoughts on “How to walk in high heels

  1. ClaireSuzanne May 3, 2011 at 3:35 pm Reply

    Excellent advice! I go through phases of heel-wearing. Some months, I’m all about heels and I’m all “no pain, no gain.” Other months, I’m all about comfort and think “what’s the point.”

    I’m in a “what’s the point” phase now and you’ve inspired me to break out some of my favourites and break this heel funk!

    • Olga May 6, 2011 at 10:54 am Reply

      Happy to help you out of your funk, ClaireSuzanne! I go through the same spurts myself. Today I’ve switched to “No Pain, No Gain”. 🙂

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