October Challenge: Daily Heels

Since I was a little kid, I’ve always been interested in fashion. I used to look at the newspaper ads for stores like Sears, Kohls, and Montgomery Ward (yeah yeah, I’m old) and get envious of all of the pretty clothes on women. But for the longest time, I never really dressed up. I feel like perhaps some of it might have been this idea from my mother and sister. They never seemed to like dressing up in my younger years. So I never really did. After all, if they hated doing it so much, and one was supposed to dress up for weddings, funerals, graduations, etc., then I was the weird one for liking it, right?

More into my adult life, I slowly started wearing heels more for fun. It wasn’t often, usually whenever I was in a particularly good mood. And I did wear dresses and skirts more often too. I rarely wore them together. And often if I did wear them, I tried to talk myself out of them for all sorts of various reasons.

When I got a job teaching a lab class at the university I was at, I decided to step it up a bit. As a software developer, I figured I, a woman in my 30s, teaching mostly guys in their young 20s, probably should try to command as much respect of the room as I could. I bought some nicer clothes and wore them on days I taught (initially 2). But as the years went on, I really liked looking nicer. There were days I started dressing up despite not teaching. I did it… for fun…   and even enjoyed it! (including heels! and dresses! and sometimes at the same time!)

But 2016 rolled around. I got into a bit of a funk. I quit dressing up as much. I didn’t feel as pretty. If I tried, I usually felt stupid for trying. I just couldn’t do it as much.

I love heels still. I envy the women I see that wear them daily, and rock them. I wanted new shoes after I saw women in them. I missed wearing them. I was envying the women I saw heading to the bar near my house all dressed up. I knew I’d probably want to explode if I kept this up for too long. So I got the ridiculous idea:

What if I made myself wear heels every day in October?

It was mid-September when I thought of this. I had some time to decide, and decided maybe run this like a science experiment. Hypothesize something (I’d be more confident after forcing myself to wear them), come up with a plan (below), document results (blog posts), and see the conclusion at the end of the month.

So I devised a plan:

  • “Heels” are shoes with at least 1″ of a heel on them.
  • Wear heels Mon-Fri daily
  • Wear heels at least once a weekend
  • I can wear emergency backup flats for really long walks
  • … for really rough terrain
  • … for physical labor
  • … if something was wrong with a shoe I was wearing (heel was about to break for instance)

I also realized that I was speaking at a conference on Oct 1, and also at the end of the month (Oct 27, 28), and had a friend’s wedding in the middle (Oct 15), so I could use these as sort of excuses to keep this going.

So I decided to go forward with it. Let’s see how I feel and if I can keep it going. I’ll keep you updated.



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