I used to think that there was a certain level of cool that I would never achieve again after becoming a teacher. It seemed to me that I was going to be stuck in the world of ugly sweaters with patches sewn onto the elbows. I would have chalk stains up my back from accidentally leaning on the blackboard too much without noticing. My image of myself as a teacher was not that great in the early years.
Since then, I have turned around my sense of fashion in a way that I was never thinking about things before. Students who used to look at me as the old guy that was teaching them old guy things are now impressed by my look. I even had a cool student ask me where I got my outfit (and I'm over 50% confident that he wasn't just making fun of me and being sarcastic).
I always knew that socks and sandals is a big fashion faux pas. It is something that my grandfather has become known for and he seems to be the king. I would never want to step on his territory and steal his look. That said, we are starting to find ways to make that sound chic and it is changing my look.
I started thinking about my look from head to toe and that was where the biggest change set in. Before, I might wear socks and sandals together as a mistake or just think of that as a footwear choice independent of the other choices I made, but that seems like an insane idea now.
The way that you can wear socks and sandals out in public and still look like someone that people want to spend time with is by planning your wardrobe out. If you are planning on showing a lot of hairy leg, maybe this isn't the look for you. If you are wearing jeans, maybe this doesn't make sense.
Most times, wearing socks and sandals just won't make sense. Consider that socks are meant to keep your feet warm, but sandals are pretty much designed for the exact opposite. That is not a look that makes a lot of sense together. That's why we've been testing things out to make it work.
One of the things that inspired me in my decision to go for the socks and sandals style was seeing how cool it looked on Tyler the Creator. There are a lot of celebrities where you see them wearing something, wish that you could wear something nearly as cool, try it out, and look like an idiot. I have made a fool of myself a fair share of times.
The thing to know about trying a new look is that you can get by with confidence. If you just sell it like you think you look good, it will look good. As soon as you doubt it, it shows. This might take some prodding, but you should try to make socks and sandals work in your wardrobe.