I have both, but I much prefer longwings. I have some old Florsheims, leather Aldens in black (Barrie) and brown (Modified last), vintage Dexters with a great patina, and some Allen Edmond shell cordovan in #8. I think longwings are great with jeans and dressed up...by far my favorite shoes. Generally, my wingtips (light brown Church's and some dark red suede Edward Green for Kurt Geiger) are more for dressing up for work. I treat good old double soled Americana long wings as my go to shoe, I'll wear 'em with almost anything.