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She Said/Then He Said: The Unfashionable Boyfriend Formula


A blogumn by Andy Allen and Kalimba Bennett

Dear She Said/Then He Said,

I really like this new guy that I’ve been dating for 3 months. He’s an engineer, smart, funny, and kind. The only thing is that he’s a horrible dresser. He mentioned in passing that dumped a girlfriend, because “she was always trying to change him,” so I don’t want to tell him straight-out that he’s a horrible dresser. But he wore an old T-Shirt and jeans with paint stains on them to my boss’s birthday party. It was so embarrassing! Please help!

Scared to Speak Up


Alright Scared to Speak Up,

I’ve got news for you sister, the old saying is true — a good man is hard to find.  If you are really into him and he’s all the things you say he is — employed, smart, funny, kind — then you should be thanking your lucky stars you found a keeper.  Period.

There are always going to be things about your partner that are not “perfect” and I can guarantee there are things about you, yes you, that he doesn’t love but keeps to himself.  So, my first reaction is to tell you to “zip it.”  I’d recommend spending less time nit-picking and more time getting to know this great guy.

But if you feel that you absolutely have to say something, here are a few suggestions on how to approach this delicate matter after the jump:

Find a way to ask him how his ex-girlfriend was always trying to change him — it may not have had anything to do with his clothes. This way you know if the clothing thing really is a sensitive area or not.

If it’s sensitive, then this is something you have to learn to love about him, because the worst thing you can do in a relationship is try to change a person. It never works and almost certainly will breed insecurity and resentment in your partner.

However, if it’s not an area of sensitivity, then he’s probably just uninterested or intimidated by fashion.  So, I would try one of these suggestions:

1.  When going to your next event, mention what the vibe is going to be like — “It’s an upscale event,”  rather than telling him what to wear.  See if he dresses more appropriately with more information.

2.  If you see something you think he would look good in while out on a date, mention it.  “That gray sweater that guy is wearing would look great on you,”  See what his reaction is.  This will let you know if he’s open to dressing differently or not and it might even open a dialogue about the way he dresses.

3.  Invite him to go shopping.  Sometimes a guy just needs a little help.

4.  Lastly, and this is a big gamble, but you can try buying him something that is a “nicer” version of what he normally wears and see what he thinks.




Dear Scared to Speak Up,

I’m very happy to hear that you’ve found someone and that things are going really well between the two of you so far, and for the most part.

Fashion is subjective, so when you say, “he’s a horrible dresser,” it’s very important for you to clearly understand that you’re saying, “I think he’s a horrible dresser.” You can only speak for yourself. If I saw him show up at a birthday party where most people were dressed somewhat formally, I might applaud him for his absolute refusal to be a slave to anyone else’s wishes but his own. Or I might just salute his absolute apathy toward something that most people get really uptight and overly-concerned about. Someone might think you’re a horrible dresser. Would they be right? No. Would they be wrong? No.

He knows what he’s skipping. Don’t you think he’s seen the magazine covers while waiting in line at the grocery store? The ones where Brad Pitt looks like a billion dollars in some suit or Matthew Fox looks better in a t shirt and jeans than I do in a tuxedo? He sees them. He knows what some women want to see. He’s choosing not to let it matter to him. If he’s kind and smart and funny, he has probably been working on his interior all of these years.

However, if you absolutely can’t leave this alone, I agree with Kalimba. Your best shot would be to periodically buy him clothing gifts (birthday, Christmas, and one or two times in between). Tell him you saw this thing and thought he’d look great in it. If you like how he looks when he puts it on, make a big deal out of it. Say that you love it when he looks sharp. That will make him feel really good. It might be enough to nudge him in the direction you want him to go in.  But if it’s not, it’s not your place to make him change.  Let him be who he is.


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Photo Credit: Bastiaan Terhorst