Downsides to Being Well Dressed

1. Maintaining clothing is time-consuming and expensive. I didn’t realize that investing in high-quality pieces also meant committing to high maintenance. I get memed by my roommates when I’m washing my Japanese denim jeans in the bathtub. I regularly shine my leather shoes. I don’t use dryers, instead I hang-dry my garments instead. And then there are the dry-clean-only pieces—which adds up over time. I like to reframe clothing maintenance as building a relationship with your clothes. Take care of your clothes, and they’ll take care of you.
2. It makes others feel self conscious. Yesterday, I was catching up with an old friend at a party and when I mentioned that I got into menswear, I can feel that they started to feel self conscious in their own fit. This happens decently often. I don’t judge people on what they wear and I don’t want people to feel bad about their outfits.
3. Everyone expects you to be fitted at all times. I feel like I can’t step out of my house for 5 minutes and go to Duane Reade without being fitted. Just in case I bump into a friend, they don’t catch me lacking. Sometimes, I don’t even want to dress up. I remember I was on a cottage trip with a few friends, I don’t want to be fitted at a cottage, I just want to chill.
4. Fashion is a materialistic hobby. The fact of the matter is that fashion is a pay to play game. And because it’s consumerist in nature, it also inevitably creates an attachment to things.
5. People make assumptions about you. In general, being well dressed comes with many positive assumptions like you have good taste and have self respect. But there are many other assumptions like your judgemental, materialistic, and maybe a bit fruity.
6. Your taste in fashion will always outpace your wardrobe. It’s like Ira Glass’ “taste gap” idea— the artists frustration is that your skill never matches your taste. In menswear, this means you’re never fully satisfied with your wardrobe because as your taste evolves, your closet always feels like it’s falling behind. This means that you constantly have a “Buy” list, and it doesn’t shrink, as your discovering new styles, new brands, and as your taste evolves.