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As a fervent supporter the of neo-prep wave, I see no reason that chinos and wingtips woudn't go together just perfect. I think they would go wonderfully, and easily with a nice neat pair of trouser-cut flat front pair of creased chinos.

They would also go great with a set of chinos that was non-creased, rumpled, messier pair laundered like a pair of jeans. Even for an apparent "prepster" like me :-D, this is the absolute far end of un-formal pants matching the wingtips go. It's kind of a nice idea to think you could wear them or something else maybe, but I think that's about as far as they go with out having too much formal/unformal miss-match.

With the "smart casual" office dress codes, and newer prep styling, you see a whole lot of formal shoe, slightly less formal outfit. It's a nice way to sharpen up your slightly less casual outfit with out wearing boat shoes every day.

For example, I have my AE Strands on right now, with some 100% cotton dockers, Bean shetland sweater, and and freshly ironed LE Hyde Park Oxford and it looks great, and even fits in a little with with what my less hip office mates are doing without scaring them completely (like a tie would, let say).

I distinctly think a lot more dress shoe flexibility is baked into neo-prep than the old most traditional of the gentlemen that post here would be comfortable. The only shoe I would actually reserve for dress-pants only are my cap toes.

Cheers to the traditionalists though! I might be doing it a little different than some people here, but I'm not worried about it. How you make something your own, that is the fun part.
 
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