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Originally Posted by Penske_Account
For starters I dont look like I am approaching middle age and I am a successful urban hipster, so I am not sure my epxerience is relevant, but, I wear one of two hats, depending on the occasion.
In my uber-urban hipster mode I go with the cashmere Gucci hat, it looks something like this, only no symbol indicating brand and its chocolate brown, to bring out my eyes.

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I wear a hat not unlike that when I"ll be around dozens of nasty shitting penguins.
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The other one is a IronMan Hawaii finishers cap (baseball lid). I wear that to the gym and on warmer weekend days when I am in the drop top, with the top dropped, running errands or going to wine tastings or putting the smack down on the h8ers and non-believers.
ymmv (merde! stp!)
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exactly. I typically where my "Pennypacker '84" cap.