A few days ago I decided to finally try and understand fashion. I wasn't a bad dresser persay, but I was clearly not trying to impress anyone. I basically had a uniform: most of the time I wore a red jacket (weather permitting) with a t-shirt, khakis, and ropers (if it was cool) or birks (if it was hot.) What kickstarted my quest was the combination of the purchase of a new Resistol hat and starting a new job. Well, the hat was actually very old, but it was new for me. When I brought the hat home for the first time I started researching the different rules surrounding cowboy hat care and etiquette. This led me to read more about boots, and quickly I was deep in a rabbit trail that primarily consisted of The Art of Manliness and r/MaleFashionAdvice. I was surprised to discover that while I didn't know anything about the topic, it seemed learnable. I think part of why I hadn't attempted to be fashionable in the past was it seemed too hard to attain. But the resources I found laid out some pretty simple steps you could take to upgrade your wardrobe and start down the road to fashion icon. Besides, I started a new job and figured it was a good time to start taking my appearance more seriously.

Now, lest you think that I am going to be the next Cary Grant, this is going to be a process. I'm not going to completely remake my wardrobe overnight. All I am committing to at this point is to think more critically about my clothing choices. But I am open to the possibility that even this will be too much, and I will revert to my old habits rather than take on the additional stress of caring about my appearance. If the steps are manageable however, and I can dress better without much committment, it may prove worthwhile.

I've already learned some valuable lessons and made a couple of additions to my wardrobe. First, mock me if you will, I didn't realize that you could wear dress shirts without a suit. I thought that there were two types of button downs: dress shirts and more casual button-downs, and that the former were relegated to strictly suit-attire. I learned that white dress shirts can actually go great with anything from a full suit to jeans, so voila, I ordered a few new dress shirts and will start wearing them to work. Second, I had apparently been rolling my sleeves wrong! There's actually specific ways to do it, and certain rules to follow (like not going above your elbow). Third, a sports jacket is apparently a necessary component of your wardrobe. Balking at the price of new ones and not quite believing I would have much occasion to wear one, I went to a local thrift store and bought a gray tweed sports coat for $2. I loved the look and it fit remarkably well, merely being a little to loose in the chest (which all suits are on me prior to tailoring). Once I have it taken in a bit I should have that box checked.

I'm excited to learn more as I go, but I have a few concerns at the moment. First, hassle. Like I said, I wasn't a bad dresser. I like to think I was actually a step above most guys my age. So remaking my wardrobe and thinking more about how I look may just add a layer of complexity to my life that is unnecessary. Second, money. I can see this obsession quickly getting out of hand, and my job that now gives me access to "adult money" does not help matters. I'll need to take things slowly and find deals whenever possible (the sports coat was a good start). Third, minimalism (or lack thereof). My "uniform" enabled me to have an extremly limited wardrobe, which was especially useful for travel. I'm a huge proponent of "one-bagging" and I am afraid if I start to care too much about fashion that will make packing in one bag more difficult. I think I will try to go ahead and go through my closet and get rid of the stuff I know I don't really wear to make room for the new stuff. I might also look into how to remain fasionable with a limited wardrobe.

Anyway, I just wanted to share my initial thoughts as I start off on my journey to fashion king. I might be really committed to this long-term and turn this into one of the many thing I view as a competition I intend to win, or I might give up entirely in a couple weeks. Hopefully I wind up somewhere in the middle.


Below you'll find some of the checklists and notes I was making as I read. You can use these yourself if you want; clicking on an item in a list will add a strikethrough.

Wardrobe To-Buy Checklist

Drawn from Your First Style Steps: Beyond Jeans, T-Shirts, and Tennis Shoes.

Drawn from How to Build Your Wardrobe: Part I

Get Tailored Checklist

Wardrobe Management Checklist