Challenge Recap: Daily Heels

There is such a weird sigma around heels. And I thought about this a TON as I decided this past month to wear heels daily. But I’ll get to that in a minute.

So the rules of this challenge were:

  • Wear heels daily Monday – Friday
  • Wear heels at least once a weekend
  • They must be at least 1″ tall.
  • I can wear flats instead for long walks or rough terrain
  • I can wear flats instead for intensive labor (e.g. gardening)
  • I can wear flats instead if I feel there’s an issue with the shoes or emergencies (e.g. feeling the heel is about to break)


As I mentioned in my intro post, I’ve always loved classy looks on women, but really have spent most of my life not really dressing up much. When I started teaching some classes, I decided to dress up a bit more. Since I was still an undergrad when I did that, I ended up dressing up more than your average student, especially in tech. But I liked it, but felt silly. I mean… when women wear sweatpants and tanktops and Ugg boots, shouldn’t I really not care either? There’s some encouragement, like this post from College Fashion saying “Uh, yeah, you SHOULD dress up daily for many good reasons,” but it’s still hard for me to be a trendsetter. I have spent most of my life with some pretty awful self-confidence issues (which I may mention in another post). It’s only been the last couple of years that I’ve slowly tried breaking out of that.

After college, I worked at a bank for a while. As one might guess, dress is a bit more conservative there. While they did eventually loosen the dress code for developers to wear jeans, t-shirts (only with company logo on them), and sneakers, a lot of people didn’t. And it was easier to dress up as the women around me dressed up more. In fact, I was usually the most critical of my clothes because it was just a thing there.

Then I moved to a new job… one where casual was a thing. My team, as a whole, never dresses up. My manager looks nice, but she’s also a manager. Some of the other admin support people dress nicer. But the vast majority of people there (and like I mentioned, my team) doesn’t. When I started there, I switched to jeans and flats. And generally felt kind of awful.

A friend pointed out to me that I probably raised my own minimum bar. Like the minimum look I need to achieve to feel comfortable. And I wasn’t anymore. But I’ve also been in a bit of a funk this year. I feel silly dressing up at this place because it’s just SO noticeable. My quiet office has wooden floors and I make noise. I’m tall anyway, but in heels I’m even taller. Just… yeah.

The Experiment

What if I did the geeky thing and treated this like a science experiment? Let’s go all out on this.

Make Observation: There seems to be this stigma that wearing heels is bad for your feet, it’s too much work, it’s only for special occasions, it’s only for short people, it’s only for businesses that are outdated and require them, your feet hurt after 5 minutes in them, and on and on. Yet… they sell a lot of them, otherwise you wouldn’t see half of a store taken up by just heels. The women that wear them rarely seem to hate them and complain a lot. The women that wear them more regularly seem to like them a lot, and seem to care more about how they look than what others think about them. I know I have loved them, and more often than not feel awesome in them, though self-consciousness tends to make me think I should do it. I also have had people say things that make me doubt why I wear them. I also tend to fight myself when I do saying things like “I shouldn’t hurt my feet” or whatever. But I also get envious of women that wear them a lot because they rock them.

Hypothesis: Forcing myself to wear heels, something I have in the past felt pretty, feminine, empowered, and more in, might help bring me out of my funk and help me feel more confident about myself, though may take up to the entire month for this to happen.

Design Experiment: I stated my rules above. Those basically designed out this experiment. I had ideas of writing down how I felt daily, but I didn’t end up doing that part.

Test Hypothesis: I succeeded. I wore them every weekday and at least once every weekend. Only one day did I feel iffy about the stability of one of my shoes and swapped it out with flats. Despite what some people said, my feet did not hurt during the duration of this (except one day I was on my feet a LOT, but my feet would hurt barefoot or in flats if I did that too).

Analyze data: I think I want to write a separate entry on a lot of the things I experienced. But I think if I recorded out all of my daily feelings, I’d see a level of confidence go up slowly over the course of the month. In the beginning I tried to deemphasize the sound and the fact I was wearing them. I tried to wear them under longer jeans to hide them more, and tried tiptoeing around the office’s wooden floors more. Towards the end it was more of a thing so I was better about the noise. And I slowly tried really looking at the women who wore heels regularly, or out where you might not expect them (i.e. coffeehouse) and try to see  just how nice it looked, how it wasn’t like a giant neon sign of attention, and try to apply that to me too. I think if I kept going, I’d probably keep it going for a while, but still decide not to wear them occasionally. But in the end, my confidence did go up some, and I still often felt overdressed, but it was ok.

Accept/Reject Hypothesis: From this, I think I think I can accept my hypothesis.

I’d be curious to hear from others. Has anyone else done a challenge like a science experiment? How did it work out? And are there things you regularly talk yourself out of doing that you really deep down want to wear?



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