dress shoes with half a break, straightleg or slight taper
dress shoes with more break, bootcut
That's a great way to go about deciding. Do you think that loafers vs. laceups makes a difference too? I don't do the dress shoes and jeans combo much, but I'm inclined to think that loafers would look better with the vamp partially obscured by a bootcut.
Other factors to note are the degree of detail in the shoe and, most importantly, the size of your foot. Very generally, there is a classical proportion of shoe you may want to show. If you have a small foot and wear a boot cut, your shoe may disappear. Also, in the history of clothes, at times when the shoe shoes more, then more attention is paid to the detail and elaboration of the visible elements of the upper -- the stitching, brogueing, etc.
IMO, dress shoes with anything other than tapered is a wee bit tacky.
I think this depends on the deffinition of a dress shoe. If you are talking the lace-up oxfords one wears with their suits to a job interview, I agree. However, if one uses the term "dress shoe" more loosely, to refer to any leather shoe that isn't a sneaker, then I think it depends on the type of "dress shoe."
This is a good thread. I've been wondering if there could be some solid guidelines for this, since we sometimes recommend this idea but come up short on specifics.
Does anyone have pics of good or bad dress-shoes-with-jeans looks?
Personally, I like the look of a dress boot with a semi-slim to slim straight leg jean. I was looking at jeans on the Barneys website, and that's how they are showing a lot of them, and I think it stacks really nicely, sort of like Get Smart's Levis that he posted.
Dress shoes look absolutely ridiculous with boot cut jeans.....if you wear a nice slim/non-chunky pair of dress shoes you certainly don't want to completely cover them up to the toe with your denim....unless you wear super tight t-shirts, have gelled spiky hair, and are named Rico, in that case, the said fit would be perfect.