Which shoes to take for a trip depends on a lot of things:
I really don't care what people think about the shoes I'm wearing. But some women really do, and would be miserable wearing comfortable shoes that don't also look fabulous, but happy in shoes that hurt oh-so-much but make them feel pretty.
When I travel without my motorcycle and will be doing a lot of walking - which is MOST of the time - I take these shoes:
Seems like a lot to men - and to women, I often get the response, "That's it?!"
For me, this has been the perfect combination of shoes. I'm big on being practical and trying to travel as light as possible. I just don't get taking painful shoes, no matter how great they might look - even if you are going to have a private car taking you everywhere you need to go, you are going to be walking a lot in airports. Plus, I hate dealing with stuff while traveling, even when I'm going to be in the same hotel room or guest room the entire time.
Backpacking
When I backpacked (I no longer do), I took just my hiking boots and my Tevas - and was always wearing one of them: the boots when I had my pack on, and the Tevas around the camp, or short hikes without my pack. For flying, I suggest you wear your hiking boots on the plane - they just take up WAY too much space for packing. It will be rotten during security, because you will have to take them off then put them back on - and it will also be horrible on a long plain ride if you are not flexible enough to take them off in your cramped airplane seat, but that's a temporary discomfort and inconvenience.
Some of my favorite photos from my travels. Very hard to pick favorites.
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