A few Questions about Sperrys and Saxx

I've been looking at the guides on the reddit and still don't think I understand when to use/not-use Sperry's, and when to use/not use socks.

For Sperry's:

I have to use pants for work (required to wear pants + polo at minimum, but no-one ever wears anything more than that). Would Sperry's with some patterned socks work here if i wore "golf slacks" (i don't know what to call them).

For summer clothing I prefer to wear 11" inseam chino shorts (I'm like 6"3ish) + Polos. I assume no socks here with the Sperry's?


For SAXX:

They have a loungewear line that I wear at home that's extremely comfortable, but they also seem to have come out with some casual sports bottoms. Would these be frowned upon to wear as a casual going out pants (And if not, what shirt would I pair with them)? I really would like just a more comfortable casual outfit than chinos or the like, and I'm just not a fan of denim.

I assume I'd pair tennis shoes with them also if I did the above route?
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