Stilettos at Sixty

Sexy Shoes Can Conquer The World!

Sep 5, 2011 by

For many, turning sixty means crossing something lofty off their bucket list.  Maybe they attempt an athletic achievement, or take a vacation at a far-flung destination, or revisit their childhood neighborhood.

I did none of that on my birthday.

First, I don’t have a bucket list. It would just depress me. But besides that, I did something much more pedestrian for my sixtieth – I decided to start wearing high heels.

When I turned 35, I became an enthusiast of Erno Lazlo products, spending my mornings and evenings religiously splash, splash, splashing to protect my skin.

At 45, I invested in a personal trainer, committed to having a better body than I had at 35.That program unfortunately ended with a ruptured disc and a week flat on my back.

For my 50th, I forgot about personal improvements and decided to treat myself to some serious bling. I purchased Black Tahitian pearls.

Ten years later, approaching my big 6-0 I went a different route. I purchased, not one, but two pairs of high heels.  Real high heels. 3 inch plus heels. Maybe not technically a stiletto, but when you spend as much free time as you can in Birkenstocks, my new footwear seems like stilettos

Even in my 20’s I was not a high heel aficionado. With bunion imbued feet, and a boyfirend/later husband who was the same height as myself, high heels seemed frivolous, awkward and a waste of money.

But now, forty years later when most of my friends are shopping for Skechers  and Easy Spirit shoes, I have decided it’s time to start wearing high heels. If not now, when?

The purchase of the first pair of shoes was business driven. I was going on a very important meeting that could have resulted in a full -time contract for many months. When I rummaged through my closet and reviewed my inventory of potential shoes, I saw a collection that reflected my work – I spend about 30% of my time as a facilitator – on my feet, all day long.

My shoes are nothing, if not sensible.

But, sensible was not the impression I was trying to make. I wanted to come across as fresh, creative and yes, a bit edgy.  I didn’t think my 15-year of Peter Fox black mules would quite do the trick. And yes, I was concerned if my feet looked my age that the potential client might think I was too old for the gig. I am 60 friggin’ years old.

To help me with this decision, I went to Nordstrom’s and explained the situation to the salesman. I also told him I was interested in a pair of spectator shoes – this advice came from my hair stylist, Denny. I trust him implicitly on all things fashionable and cool. And so I was hoping to find the perfect pair of spectator shoes.

Fortunately for me, Nordstrom’s had just gotten a new pair of Anyilu spectator shoes that very day. They were talking to me. Big time. I had to have them.  Cream with a black toe and brown heel, it was love at first sight. Only problem, the store didn’t have my size. So I tried on a pair of Anyilu black pumps to get a sense of sizing. 

Then, Nordstrom’s did what Nordstrom’s does so well – they had the shoes in my alleged size, shipped to me so they would be ready to go to California for my trip.

When my fabulous pair of Anyilu spectator shoes arrived, I eagerly put them on. As I squeezed into the shoe, visions of Anastasia & Drizella, Cinderella’s large footed stepsisters, dominated my mind.

The shoes definitely felt too small. But I was leaving in 8 hours for California and if I didn’t take those shoes, I wouldn’t have any  fabulous shoes to wear for my very important meeting.

I told myself that the shoes would stretch.

If they have stretched, it isn’t enough. These are not comfortable shoes. Even though I wore them for several hours in my hotel room the night before the big meeting, by the time I caught the cab to go back to the airport, I was untying the shoes and putting on my comfy cozy Arche sandals and asking myself if I had lost my mind.

My fabulous spectators felt like a vice on my feet.

Over the next few weeks I bought a variety of products that promised to solve the pain. From full-length insoles to a shoe stretcher, I tried everything to make these shoes something I  could wear for more than a couple of hours.

You’d think that I would simply acknowledge my momentary flirting with footwear that is totally inappropriate for my age, and call it a mid-life crisis. But, a mid-life crisis would have happened 15 years ago for me. I’m not sure what you call doing something so very out of character at age 60.


So instead of admitting defeat, I  bought a second pair of heels – these from Kate Spade. com. I got them for 50% off, and I thought they were just wild enough that people might start questioning my sensible exterior.

While my Anyilu’s are a size 11, I had to return the 11’s I ordered from Kate and replace them with a 10 1/2. While the pain of these shoes is slightly different than the pain from the Anyilus, top of foot vs width of foot,  they still hurt. A lot. It’s amazing how many different ways your feet can hurt when you abuse them.

I was so disappointed, especially since I took the time to read the reviews on Zappos where shoppers shared how comfortable this particular style shoe is.

And maybe if I had twenty-year-old feet instead of sixty-year-old feet, these shoes would be comfortable on me too.

So now I have two pair of high heel shoes that I love looking at, but feel very sheepish wearing. I mean really. They hurt my feet!

Yet, I am not willing to give up on them quite yet.  I still love them. Here’s the thing about wearing heels when you’re not used to them: It does make you feel young. Not twenty young. More like the kind of young you were when your mom let you play dress up, put on lipstick and walk around the house in her high heels.

Putting on my new shoes makes me feel that way. Kind of giddy. Kind of giggly.

It makes me feel like there’s  a big bad world out there for me to still conquer. I just have to put one foot in front of the other.

About the Author

Elana Centor Has Written 6 Articles For Us!

Elana’s vision of a world class enterprise providing social media training, coaching and consulting is the foundation of DWT’s conception and development. Her distinguished 30-year career as a marketing expert, journalist, author and social media pioneer gives DWT the authority to succeed.
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  1. Hi Elana,

    as someone who often wears high heels, I can tell you that, even if you are good at wearing them, it takes a heck of a lot of time to find a pair that fits properly. If you’ve never worn them (or not worn them much) it’s best to take a bit of advice from RuPaul: the higher the heel, the better it is for them to be open toe. I know that sounds weird, but the foot slides forward in high heels, and if your feet are wider in the front, and you’re not used to heels, open toe relieves the pressure that can occur with closed toe. My latest pair of high heels is a pair of lipstick red slingbacks with 4 inch stilettos and a 1 inch platform. They’re made by Guess (also important to get well-made high heels, not cheap ones) and are quite stable. Although I had to take them in a size 8 rather than my usual 7 or 7 1/2.

    oh, and if the shoes are leather, you can definitely get them stretched by a shoemaker. Adding padding doesn’t hurt, either. but you dont’ want to over-pad them, as depending on the kind of insole, the shoes might indeed be less comfortable: insoles, depending on the type of material they’re made from, can take up a whole lot of room. They your foot doesn’t fit totally in the shoe, and they can be just as uncomfortable as they are without the insoles.

    ok, I guess that’s it for me. If you decide to try them again, good luck 🙂

    • Elana Centor

      I haven’t given up. Both pair are at the shoe makers as we speak. I’m picking them up tomorrow with high hopes that some professional stretching will make them comfy. Thanks for all the great advice !

  2. Patricia

    Although I’m a little older then 60, 63 to be exact. I too love shoes but my poor feet just can’t handle heels, at any height, anymore. Guess I’ve worn comfortable shoes for so long my feet rebel at the thought of being squeezed into any fancy shoe. Keep hoping some day though, some day.

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