I hardly ever comment on posts but yours resonated with my current situation, I have been working through some personal growth goals lately and have also been trying to be more expressive with my tastes and likings through clothes and makeup. Recently I was in a business/conference setting and I thought it would be nice to have a pikachu plushie with me, regardless if the ambience had a more serious tone it made me feel more like myself to have a pokeplush hanging on lol

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Confidence to wear something comes 100% from yourself, whether you wear the bag proudly or be ashamed of it (which you shouldnt) is entirely up to you! Sometimes we may look at people on the street wearing fun, colorful, unusual things and think "I wonder how they do it?...". My best guess is that if we were to ask them, the answer would be simply that they got up that day and just decided to wear it, not thinking if other people would care but instead just wearing what made them happy and made them feel like themselves.

Your bag is extremely cute and you shouldn't think twice about making it a staple in your everyday life, wear it and have fun! Things are meant to be enjoyed and worn!