How Important Is Style Really?
My Experiment of Wearing Exclusively Bad Style
We’ve (or maybe just I’ve) been trying hard to discover personal style - to figure out our modifiers, get the right wardrobe ahead of fall/spring/summer/winter. We think about what our style communicates about us, watch style classes, and search endless sites to find that perfect shoe. But how important is style, really? Have we (again - or just I) looped our brain into an endless task just to keep it busy, without much meaning otherwise? I decided to dress badly for some time and find out if style truly matters.
In all honesty, I am no stranger to bad style. In fact, I used to completely ignore my clothes or dress really badly for a long time. I remember one instance when I was an intern in a bank in my early 20s and wore my heels down to the extent that only half of the heel was still there. My parents visited me on their European trip and, horrified, dragged me to a shoe shop to find new shoes ASAP. I was unfazed.
In another instance, I went to meet potential partners in New York with some kind of startup delegation. I was staying in a hostel without a full-length mirror and wore a dress that probably was supposed to be a tunic - so short that I could barely bend to change a slide while doing a presentation. We went to The New York Times (!) of all places to present our startups, and I had to make elaborate moves to avoid the dress riding up. Thankfully, I wore opaque tights, but the feeling was terrible.
Nevertheless, now I feel pretty knowledgeable about style. Yes, I do miss an outfit here and there, or sometimes just don’t try hard enough, but I wanted to understand how important style really is after years of a Tibi-infused brain - and how breaking these rules would make me feel.
The bad-style experiment is something I procrastinated on for quite a while. When I first came up with this idea, my brain immediately started plotting: I can’t do it this week because I have event X; next week I’ll be in this type of business meeting; and so on. It showed me that I can wear anything (i.e., do this experiment) when working from home or meeting family - I feel very secure and accepted in this environment. I also don’t mind wearing anything around friends, but when a friend had a birthday celebration, I felt that dressing badly would be somewhat disrespectful to the party she was throwing.
On the other hand - business and networking events - phew. I dreaded dressing badly for an event with a lot of high-profile business leaders, which I think illuminates the areas in my life where I’m less secure and try to patch things with superb style - or simply where people don’t know me, so first impressions matter more.
So what constitutes bad style? I wanted to come up with ideas that would be genuinely uncomfortable to wear, and decided to lean into aesthetics I viscerally dislike. I also realized this is extremely personal, and these looks might be perfect for others. Here’s what I came up with:
Feminine ruffles girly. I don’t know why, but ruffles and ultra-feminine elements always look very bad on me - like a woman in a doll’s clothes.
Overly slim outfit. I feel extremely exposed. I hate it, but I will do it.
Stuck-up conservative overdresser. I’m dreading this one - no ease or effortlessness, dressing extra maturely for my age. It feels against my look and personality, as I am quite flexible in nature and do not really like very stringent “vibes”.
Basic outfit. Slim jeans, simple top, basic shoes. No style rules followed. I don’t feel terrible about it, but definitely won’t be impressing anyone.
Boho queen. Patterns, prints, flowy materials. Natural spirit singing in the rain. Even if feminine, it’s just so not me.
Mismatching outfit. I think this one is the hardest - to truly make an outfit bad is surprisingly complicated, especially when you’re trying to.
Crazy fashion person. Over the top, full of herself look. A bit foreign to me, but let’s try it.
The rule for this challenge is to dress like this for a day when I leave the house and meet someone outside my immediate family - and see how it goes. Let’s roll and wish me luck!
Do you have aesthetics you viscerally dislike? Let me know in the comments!


