I like the no-sock, dress shoe look for summer.
Id like my pants to show a little ankle, but not too much.
How much should I hem my pants? (in this example, I am looking to shorten some fitted linen pants)
Because of the physical differences from individual to individual, there is no formula. If you are having a tailor hem the trousers have him/her pin the trouser and see if that is what you want. If you are hemming the trouser your self ,do the same thing.
Moved this to the Menswear Advice forum...you should be able to hem them so they just graze the top of your shoe, but still show a bit of ankle/sock.
+1 to all of this.
even shorter when you're riding your dutch bike but it probably makes more sense in that case.
while i know it doesn't answer the op (I would just ask for no break [altho shivering break is an amazing term and will probably impress your tailor more]) i think that that look is about as faddish as say lower rise, flat-front trousers or sack coats which i find to be just as juvenile as (and yet essential to!) the "browne" look.
you could also consider tapering your trou to create a little negative ease and make the hem tailoring more apparently purposeful.
fwiw i like the look.