I think it comes down to wool
I will wear a wool shirt more than once - and it doesn't smell. I will not wear a cotton shirt more than once, because it does smell (I'm a stinky person).
I also hate carry ons, though - My blood boils everytime I fly and I see people with 2 Large carry ons - pushing the rules so now I have to get hit in the head with their cr*p. Pet peave rant over
I purposefully bought an wonderful carry on bag that was an 1" smaller than the requirements and love it.
However, for a Euro trip, I'd carry a duffle, not a rolling bag.
But, I think Oak hit the nail on the head - how much do you care about what you look like? What is the purpose of your trip? I carry more for business travel, in fact I carry extra because I absolutely must change into casual cloths as soon as I'm out of the meeting.
I also love my vibrams - I used to carry jogging-type shoes, boots, and slippers. I don't need boots anymore, minimalist almost always works.
Edit to say - I'm a shutter bug with way too much camera equipment - I carry as much camera equipment as I do cloths - so I often check the cloths and carry a backpack with camera gear.