Thing is when I brought it up he gave the argument that he isn't allowed to decide anything about my appearance so why should I dictate his. Technically I agree with his point but I still find it a trial not to shear him like a sheep.
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once he goes in for a serious job interview with a haircut like that he won't be taken seriously lol
but to answer your question, yes and no.
my girlfriend has used occasions like holidays and birthdays to buy me clothes she thinks would look good on me, and for the most part, I like her selection. who else am I trying to impress anyway? but its also because she knows what id like and doesn't get me anything id be uncomfortable wearing.
I would absolutely hate it if she bought me an article of clothing that I just felt ridiculous in. Same thing should be with your boyfriend. Tell him what you personally would think looked best on him. If he's uncomfortable with it, than he just is, and you should embrace his individuality. and if you can't, you probably don't like him enough anyway