COLOR ME JEALOUS SON. Make sure you drink sangria and cuba libres in spain and remember, no cappucino after 11 in Italy. (or something like that).
To be honest, I’d wear the imogene and willies as long as they’re comfortable. If you’re into the whole ‘not washing your jeans often’ thing and enjoy watching them age and fade, why not bring them with you? Then you can tell people you broke them in by traveling through Europe. “Oh that rip? I caught it on the portcullis of a 16th century castle I was in.” HUMBLE BRAG AT PARTIES IS NOW ACQUIRED.
As for shoes, depends on your style. Some would bring a comfy pair of boots, others a loafer. Me? I’d probably bring a pair of desert boots as long as I knew I wasn’t going to be doing any real hiking. Desert boots are easy to wear and can be dressed up in a pinch.
Enjoy and safe travels.