I’ve been reading Marie Kondo’s The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing on and off for the past few months. I recently bought some new clothes taking advantage of a Black Friday sale on Bonobos and also a sample sale by our client Gitman Bros. I thought it’d be a good opportunity to reassess my wardrobe and get rid of some things.

One thing that was immediately apparent to me was that I just have too many t-shirts. Over the years, I’ve amassed a number of t-shirts from work, various startup events, athletic competitions, and online shopping. I decided to do a purge and really went at it. I know MariKon method was to ask if each piece of clothing brought me joy, but I went about it in a bit more pragmatic way. Any negative answer to the following meant the shirt would get tossed. Here was my decision tree:

• Does it still fit well?
• Are the collars frayed?
• Are the colors faded?
• Do I still like the design on the shirt (if it has a graphic)?

I was able to toss out about a dozen shirts this way, and with the shirts that are left, it’s definitely easier to say “this piece of clothing brings me joy.” Afterwards, I took to the MariKon way of folding clothes and reorganized my dresser to have all of my shirts standing up so I can see them all at once. I’m not sure how sustainable this is, but right now, things look really neat.

I repeated the process for the sweaters and my dress shirts. I also introduced some taxonomy into the way my dress shirts are organized so that solids, plaids, and tailored shirts are grouped together. I never paid much attention to the organization of my clothing in the past, but it was refreshing to take stock of everything I own and to know what combinations are possible. I also like that I’ve been able to dismiss pieces of clothing that only made me feel so-so.

Besides middle school and parts of high school, when it was possible to get made fun of for wearing something off, I never paid much attention to clothing. I did have a phase when I collected a lot of neckties, but I grew to despise wearing them and got rid of my fifty-plus necktie collection some years ago. Recently, I’ve been paying more attention to clothing than usual. It’s not that I wish to be fashionable all of a sudden, but I’ve been trying to find a reliable brand that delivers fit and an appropriate style. I thought Everlane was the brand for me, but after a couple of years, I realized that their clothes fit me poorly (their smalls run a bit loose) and the construction of their clothing is terrible–they seem to fall apart after a half a dozen washes. These days, I’ve been buying mostly Bonobos. The fit is much better and I like the selection of their styles. Hopefully, their sweaters and dress shirts will get a good amount of use. Hoping one day there is a brand that makes a range of clothes that truly fit my body type–broad shoulders, short arms, and short torso.

I’ll admit that, with a slimmer physique owing to a better diet and more exercise, I’ve wanted to wear clothes that accentuate the “fit”-ness. It’s a nice confidence booster. And by making sure my closet is well organized and stocked with only the clothes I want to wear, I’m taking the extra step to automate the process and reduce the cognitive load that dressing up has on me each day. I’m not yet at the stage where I’ll lay out my clothes the night before, but I’m pleased that there’s been much progress in what I wear and how I get dressed.