Question: “My boyfriend has terrible style…I especially hate his ugly sneakers but he thinks he looks great and I don’t want to hurt his feelings. How do I get him to start dressing more fashionably?”
Brian: I like this question a lot because I think it touches on a lot of deeper issues that really need to be addressed. Like, does my girlfriend think I have terrible style? Does she hate my ugly sneakers? And how does she get me to start dressing more fashionably?
Or how about these: how can your boyfriend get you to like better music? Can he make you dump that friend of yours who he finds annoying? How does he get you to start dressing more fashionably?
I’m obviously teasing you but I think you get my point here. Fashion is subjective. Your boyfriend likes how he dresses and I assume he derives some level of confidence from how he looks. It seems a little unfair for anyone to try and change that, just as it would be unfair for him to try to make sweeping changes to your taste in movies or books or clothes if he didn’t like those.
That’s not to say you can’t give him a little encouragement. If you’re out together and you see something that would look great on him, tell him so. Say, “this is really nice, I think it’d look great on you.” In fact, say those exact words. Don’t make him try it on, don’t force him to buy it. Try to avoid saying things like, “hey, for a change of pace, here’s a shirt that doesn’t look like it was stolen from a homeless person” or “if you’d rather I not break into hives when I look at you, try this on.” The subtle approach plays to the fact that he probably wants you to find him attractive but it also allows you to avoid confronting him on his style choices. Plus he won’t dump you for being selfish.
In the end, your boyfriend is who he is. You are who you are. And when he agrees to watching Love, Actually with you for the 19th time since you met him, try to remember that ugly sneakers aren’t the end of the world.
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