what shoes do you wear with grey wool trousers/ chinos?

grey wool trousers- i've always worn black double monks but that pair saw it's last legs last year. i'm thinking of dovers (split toes) in brown of course for a more grown up look or a plain toe blucher maybe 5 eyelet with a roundish toe. i don't seem to like wing tips very much but i guess i can see myself wearing a blucher in black. chinos- i've been wearing chocolate suede penny loafers. they feel like a weird pairing is all i can say. i was thinking of wearing blucher mocs/ or a chukka moc but those may be a step down. looks fug in the pic. might look fug irl too. can't remember or find online what i saw in the store though. also what about an alden tassel loafer? what else is there? gucci loafers, not so fond of them anymore. venetians are probably my favorite but it's hard to find a good pair. http://blog.leffot.com/wp-content/up.../dsc_07131.jpg btw i don't wear sportcoats very often. usually just a dress shirt/ trousers with no tie. edit: i guess the dover image doesn't show up but you know how it looks. anyways do you think my picks are too "old man"? should i just purchase another pair of monks and jm weston loafers maybe in calf tis time?

Oxblood - probably as a loafer (not penny loafer though)

i do have a red 2 eyelet derby from carmina. i mostly use it with jeans though since they are pretty sleek.

Originally Posted by Macallan

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Oxblood - probably as a loafer (not penny loafer though)

Why not a penny loafer?

i can't remember which blog i read it on but has anyone released like a gunboat loafer? like a pretty big style penny loafer w/ double soles? it could be the marc mcnairy new amsterdam but i remember the author of the blog gave a play by play why that particular loafer was awesome. been trying to find it for a couple of days now.