Category: Fashion Challenges

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?



November Challenge: All Dresses/Skirts

I decided about the middle of the month that maybe I should do something else for November. I love skirts and dresses, but tend to talk myself out of these a lot too. Especially if it’s really windy outside. So what would happen if I told myself I had to wear something daily? The plus would be that now that it’s autumn, and I always want to wear more tights, this would be a good excuse to do it. I also get a bit envious of women that do it daily, and have been asking myself lately, “Why can’t I do what other women do? Especially if I’m so envious of it?” So it’s going to be a thing.

So I’ll report in at the end of the month to see how I felt or what I think about all of that.

~ Sarah

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.