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Why you shouldn't wear a bow tie: You'll look like a tool.

Sorry - but in general any "wacky" clothing generally misfires drastically.

:-) Someone should do similar for the leather trench coats people started wearing after The Matrix.

I did that. But it got stolen. I'm never getting into Zion now.

So, you're suggesting that Sir Winston Churchill looked "like a tool"? There are many individuals over the years, who have looked very stylish in a bow tie. As @mberning points out with his image, the fact that some people look like tools wearing an item does not mean that all people look like tools wearing one.

I think Winston was sporting them 50 years ago.

But what if it spins around like a propeller? I mean come on.

Depends if you're a children's entertainer or not.

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