YOU ARE THE ADVICE COLUMNIST: How Do I Get My Husband To Dress Like An Adult?

So, how do I have an adult conversation with him about his juvenile wardrobe?
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Charlotte got to come say goodbye to our offices after school yesterday. She often stands like that.

I am married to a wonderful man. He is smart, kind, funny and an awesome dad to our daughter. I also happen to find him dead sexy. 
The problem is that he is almost 35 and still dresses like a teenage AV geek. For example, one of his favorite looks is a black t shirt featuring not just one, but two dragons, baggy, holey jeans, and a freaking bandanna tied around his head. He will sometimes add a fringed brown suede jacket to this combo. I'm not one to care too much about other people's opinions, but I have to admit that when I get all dressed up for date night and he wears this, I kinda feel like a dingus.
I've been buying him new clothes that he does wear when prompted, but his default is the graphic tee and head bandanna. He works an internal IT position, so nobody really cares what he wears to work. 
A lot of these clothes, he's had for at least the ten years I've known him, and I can't just toss them all at once without talking to him about it. I've already secretly disappeared his bucket hat, velvet v-neck and the short sleeve Hawaiian shirt he thinks makes him look like Hunter S. Thompson is on it's way out the door. 
So, how do I have an adult conversation with him about his juvenile wardrobe? Or do I throw a fit about it?  Tears? Threats? Bribery? I'm open to just about anything.

How would you let him know his clothes are sub-par? Let her know in the comments!

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Posted in Relationships