If you know me, then insecure is not the first adjective that comes to mind.

But like almost every human being, I naturally have some insecurities. I have a horror of being over-dressed. Strange though it may sound, nothing makes me want to shrink up and die more than being out of place because I am too dressed-up or decked out.

And like many people, to counter my insecurity, I take it too far in the opposite direction and prefer the security of being casually dressed. Unlike my mother who is always impeccably put together.

Consequently, I rarely wear skirts or dresses because, to me, they give the impression that you are trying to make an impression even if it’s just to go the store, or out for a meal, or to the office. (And I wonder why my daughter has an aversion to skirts and dresses … hmmm … Go figure.)

So what does his have to do with shoes, you say?

I love shoes. I obsess about shoes. I have a Pinterest board littered with exquisite examples of them. I used to spend hours as a teenager designing imaginary shoes, my school books filled with doodles.

I also detest breaking in new shoes. Blisters are one of shoes’ many way of punishing us. When I do wear any shoe with a heel more than one inch, I quickly me realize I‘m not as young as I used to be, as I always wake up the next day with my hips feeling like they are back to front, my knees tender and my back shrieking.

And yet I look around me, especially at the feet of my colleagues at work who effortlessly and beautifully sport gorgeous, stylish and dramatic heels, day in day out, with grace and style and confidence. Without grimace or clumsiness – or appearing overdressed. Or complaining of achey backs and joints.

I want to be able to do that. But I’m scared of looking like I’m trying too hard, looking like a phony or a mutton in sheep’s clothing. At the core, I’m scared of drawing unwanted attention to myself. Heaven forbid I should look womanly, a by-product of arching your feet, extending your calf muscles and having to walk with an exaggerated sway, like Joan from Mad Men.

I know this is ridiculous. So I am taking baby steps to remedy my insecurity. A large part of this is my road back to finding the woman that’s been buried under the messy morass of motherhood. She’s in their somewhere but most of the time does not have the time or energy to make an effort. Looking presentable is accommodated through safe, colorful, always comfortable clothes, plus lots of lovely jewelry and a smile. But this Mom has started taking measures to reclaim herself, including reinstating the pre-party before an evening out, ensuring she is not harried and can linger over her choice of clothes and preparations.

Last week, I took my therapy one step further. Having waiting several months, scoured though many web pages, catalogs and pins, I finally splurged on new shoes. I didn’t go all-out Jimmy Choo (the dollars don’t stretch that far!) and I didn’t select anything ridiculous or, heaven forbid, impractical. I played it safe and, don’t laugh at me, shopped at Clark’s, seeking assurance that my feet and posture were in the trusted hand of a sensible brand.

I love the shoes I bought, Even the sales assistant remarked they were the only ones that didn’t look like Clark’s. I wore them out to dinner that evening, with jeans, of course (just in case anyone was looking.)

On Monday, it came time to get dressed for a day-long business trip. Here goes, thought I. I selected a dress – a safe, black, comfortable one, already tested once for its non-attention drawing values. I strapped on the heels, walked gingerly like a new-born deer to the mirror. A leggy trollope looked back at me. You fake, she sneered. Do you think you are still 20? What are you trying to prove? My stomach lurched. Off came the heels, replaced swiftly with some safe shoes.

I kicked myself all day for not having the balls to do it.

The following two days, I made up my mind to give it another shot. Day 2, I wore the heels but under the cover of pants, a safer combination. Day 3, I took a deep breath and wore a skirt and heels.

I felt very self-conscious. And tall. I also felt powerful, confident, and dare I say, womanly.

But the funny thing was, I don’t think anyone even noticed. So maybe, just maybe, I actually fitted in more and it’s my casual wardrobe that’s doing me a disservice?

I’m not going to be found sashaying in my new heels every day, that’s for sure. You’ll still find me in my comfy, safe flats/clogs/boots. But I’m determined to strap on my heels and even a dress from time to time, and wear them with my head held high, my tummy sucked in and a subtle sway of my hips.

Maybe someone will notice? Maybe I won’t be terrified of that? After all. What’s wrong with a little attention?