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True dress shoes are not the best look with jeans. The wingtips that are pictured are on the casual end, even on the casual end of wingtips, so they might work.
If you're thinking of something dressier, like a black captoe, I would discourage that combination.
I like those. And the high tops are a good idea with cuffed pants. Those would also look good with darker jeans for a more formal look, with a sport coat.
Like many other fashion fads, the recent look is wearing blue jeans with dress shoes and even wearing sneakers with a suit, obviously two opposing looks that have been recently popular.
The blue jeans with the dress shoes, in my mind, was usually europeans who only wore leather dress shoes so they would wear them with blue jeans all the time. This even evolved to the second generation for the “NJ Guido Look” for guys like Tony Soprano.
Although it’s a modern day trend and fashionably accepted we can individually decide if that look is for us.
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