Finding Confidence to Wear Cowboy Boots in the Office

wearing cowboy boots to the office
January 6, 2023 Jeremiah Craig 0 Comments

As 2023 begins, many of us are exploring new things in an effort to become the best version of ourselves. This could come in the form of working out more, reading more or maybe wearing cowboy boots more.

I received an email this week about wearing cowboy boots with a higher riding type heel in the office and I wanted to share it today in a post because I know this is something many folks struggle with. I’ve changed the name to help with privacy.

Below is a picture of my old Abilene boots with a 2″ heel while on the bus to the content marketing job I had in Seattle in 2018.

The Email:

Subject: Confidence on wearing cowboy boots

Hi Jeremiah,
Thanks for sharing all your information in cowboy boots. I always liked cowboy boots but never found the confidence to wear them. In a white collar job, nobody wears them at work. I found this great pair of Olathe brown buckaroo boots locally through Craiglist, but they have a 2 1/2 inch heel, which makes them very noticeable so I just haven’t found the courage to wear them, I may get some jeans that may hide some of the heel or perhaps I need to consider wearing a lower heel boot to start with. I appreciate you insights.


My Response:

Hi Jorge,
Congrats on the boots! Olathes are a quality brand and they should last you a good long time. I remember wearing cowboy boots at my white collar jobs too and only a few people ever really notice. When they did, I often got more comments about how nice my boots were.

I would always get more sarcastic ball busting comments in the blue collar jobs I had but that comes with the territory and is more of a friendly banter kind of thing.

If someone gives you a negative comment about your boots in the office or simply asks you “what’s with the boots?” then I would suggest you just be honest and say that you’ve always liked the look of boots and are trying it out to explore something new. Give them the entire story about why you’re interested. Opening up to others helps us make new friends or strengthen current relationships which is nice in life but also helps us in the office when we need to collaborate with another department. I often share my entire thought process with those who ask or scoff because it shows how secure I am in my decision to wear what I choose. Even if I’m just trying out a new style to see if it works. If they make a joke in passing, I’ve found that the passing reply “You don’t know what you’re missing!” works well.

If people care that you are willing to explore new things (even if it’s just boots), I’ve found that they either become inspired or insecure.

Some might think, “Wow, Jorge is trying something new that he’s always thought about doing. Maybe I should try wearing that leather blazer I have more often”. The blazer is just an example but you get what I mean. Others might think your boots are stupid and don’t belong in the workplace but as long as none of them are your manager, it doesn’t matter what they think. They are ultimately insecure that you have chosen to live your life how you see fit and somewhere deep down they are struggling with the courage to do the same.

A 2.5″ heel is definitely a tall riding type heel but as long as they don’t hurt your feet and you like the extra boost in height you get, I wouldn’t worry about finding pants or jeans to cover the heel. That’s the heel style John Wayne would often wear! You may find with time that you prefer the comfort of a lower heel but you’ll never know until you try your Olathes out on a regular basis. You may also find that the higher heel might get more comments and start conversations and in those conversations you decide that you enjoy the higher heel or you decide to try something different. Either way you win because you are learning more about yourself and what you like in a pair of boots.

I always encourage people to step in the strongest way. Not only in their boots but also in their minds and in their actions. You may find that just wearing the boots to the office will give you all the confidence you need to overcome anything. Just the act of wearing boots can be a huge confidence boost and make you see the world a little differently (even if it’s at a little taller angle).

I hope this helps. I’m very excited for you and your Olathes. You made a great decision to buy second hand especially with such a great traditionally made brand. Those boots should last you a long time.

Cheers buddy and happy new year! Wishing you the best.

Step in the Strongest Way

I wanted to share this email from Jorge because it’s one that I get on a regular basis from others.

This is the year to wear boots to the office just because you feel like trying it. Or to continue wearing boots because you know that’s what you like best.

Start small. Maybe just wear boots on Tuesday. I call it Tuesday Boots Day! Then work your way up to wearing them everyday.

No matter your strategy to wearing boots in the office, live life for you because it is YOUR life after all and right now is a great time to start it.

If you have questions about cowboy boots (or anything else for that matter), head on over to my contact page and send me a message!

Happy 2023!