Depends on what you call a dress shirt. There's plenty of button shirts made to be untucked that look great with jeans. Any shoe pretty much goes nowadays too.
If you're strictly referring to the Gordon Gecko french cuff shirts, I get it.
This is what I sometimes do. Have some shirts made that are designed to be worn casually, and just wear those over jeans. Chinese collars, simple cuffs, tapered like hell looks good on me.
Should keep my weight stable though, because now they are all hanging there gathering moths...