Seriously -- my take on "dressier" shoes with denim is that if the shoe is intended to be an ultra-fancy dress shoe, then think twice. Most of what we consider "dress shoes" aren't actually dress shoes in the Victorian (or whatever) sense. Example: would you wear Park Avenues or tuxedo shoes with jeans? You might, but probably shouldn't. Go for something that has a bit more personality, like most of the wing tips or monks linked to above. Aside from the make of the shoe, the make of the jeans is important too -- something with a slimmer (not necessarily skinny) leg opening is usually best. Big leg openings are too casual and too 90s for proper shoes. You've also got to think about color of the jeans with the color of the shoes. IMO black jeans are difficult to pull off with dressier shoes -- you run the risk of looking like a rich biker with no taste/ex-member of The Clash who went to business school. Same warning for very light wash or highly faded jeans (the risk there is that you look like you're 12). Darker indigo jeans are easiest and best to wear with proper leather shoes. I think pretty much any color works with them, which is why they're blue jeans. I'd actually look through the Alden thread in SW&D and see what people are wearing with those shoes (and not just Indys). This is obviously not to say that Aldens are the be-all end-all of casual nice shoes, but they're a good fit for that market and are popular with people who want to wear wing tips with jeans. Also, longwings and suede haven't gotten enough mention. Both are famously versatile and pair well with denim.
Thanks for the tips, i get most of it, but i''m a bit puzzled about no-no to captoes, to me they seem to work great, as long as they're not too shiny. I mean, a lot of wingtips are actually captoes. with wings.
reason i dont really like black captoe shoes with jeans (especially black balmoral cap toes) is because i've yet to see some that dont look like sleek dress shoes that should be paired with a suit or something. I do, however, have an old pair of brown captoe shoes i wear with jeans somtimes, but i kind of wish they weren't captoes.
as for wingtip brogues, super shiny ones i dont think would work too well, and would look too busy, but something like a paul smith dip dye miller:
I think would work great with jeans, because they're so slim with slim soles, and have more of a matte finish to them.
The shoes are quite sleek and are a black medallion toe as you can see. The jeans are not very tapered at the hem, and are of a mid rise, sort of 501 fit. Despite the general wisdom of slim leg + more casual dress shoe, i think this works.
But i think this is a case of jeans being more formal, rather than shoes being more casual.
Someone post some more pics.
swap out the oxfords for a blucher boot. smaller belt buckle wouldn't hurt, either.
Those aren't perfect, but they would be ok. I would prefer a more modern silhouette to go with jeans, like something from Vass or C&J. Not everyone has access to those options, however. Be sure to avoid chunky, wide shoes if you are going to wear slim fit pants. Slim fit pants and jeans need shoes with a slim silhouette. Larger, chunkier shoes are more appropriate with bootcut or relaxed fit pants. As others have said, brown shoes go best with blue jeans. Don't wear black shoes with blue jeans unless (a) the jeans are black or near black -- like unwashed selvage, or (b) the jeans are very dark and you are wearing a black top.