While people are sort of right about how life's too short to be worried about cringe, cringe does definitely exist, and people will always unfortunately judge you for things.

If you're a self conscious person, but you're happy with the way you're experiencing life, then continue to live life in a way that you're comfortable. I'm confident, but I'm also quite self conscious, and on the whole enjoy being quiet and humble, watching the world go by. I like to blend into my city's mid toned navy, brown, green and grey colour palette. As such, and I don't mean this as an insult, I personally would not be most comfortable wearing such a brightly coloured (garish, perhaps) watch, nor the Pikachu crocs somebody posted.

It really depends what vibe you're trying to put across. Fashion can be a signifier of interests and subcultures. I could probably sort my workplace by fashion and it would directly correlate friendship groups, music taste, and so on, without anyone of them really intending on wearing a group signifier. This G-Shock watch, I am sorry to say, by my harshest judgment, could be sorted into the harry potter/funko pop adult fashion category.

At the end of the day it's about how you want to be seen, and what makes you happiest to wear. But to be frank, yes, a big red G-Shock could be considered cringe to those who are cringe-inclined. To those who aren't cringe-inclined, it's just a big fun colourful watch. One can only respect the boldness.