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Long sleeve wool polo - with a shirt underneath?

smittycl

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DorianGreen

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Drake's does this with rugbies.

Your primary issue is that the polo is far too tight. If all of your clothes fit slim, then stuffing an extra layer in between your shirt and jacket is bust asking for trouble.

Then... the Luca Faloni model is, unfortunately for us, very pretty. Layering in this way is not practical for most of us -- a boring collared shirt on top of a boring collared shirt just looks wrong unless you're just so pretty that your face carries the outfit. This is what Drake's gets right: their rugbies are weird. They have complex color schemes. The heavy jersey of a rugby has this paradoxically stiff slouchiness to it. It sticks out in a careless way that makes you think this guy is sloppy... except he's also wearing a tie and a sport jacket, there's clear intentionality at play, a mixing of sporty and formal elements.

Maybe that's not what you were hoping to read. But I think that's how to crack this problem.

Frankly not a look I like and pursue, even though I wouldn't say that looks bad. It seems to be part of Ivy Style. You have to choose the rightly complementing garments, that is rather casual.
 

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