For my upcoming travels, I’m of course looking to minimize what needs to be packed. At the same time, I’m looking for a good pair of walking shoes. (It’s a largely urban trip, no backpacking involved.)
So the question for the fashionistas is: what kind of shoe looks good whether I’m wearing jeans or shorts? Any at all? Or am I destined to choose between looking like a dork part-time vs. packing an extra pair of kicks?
I have a pair of soft-leather brown ankle-length Timberlands. In long pants they’re fine; in shorts, they’re OK but only if you have short dark socks, pushed down to the top of the boots.
That said, in Australia in September it’ll be warm enough that you’ll probably want some flip flops (“thongs” in Aussie lingo, I kid you not). Or a pair of Crocs, which I recommend unconditionally and they only weigh a few ounces each, which is good for travelling.
Pink ostrich cowboy boots.
I’d expect nothing less from a fellow Texan 
Saddle oxfords? Wingtips?
Seriously, find some mid-cut hiking boots, they look okay (not great) with jeans and shorts. I find walking in cities to be harder on my feet than hiking. The main downside to travelling with these is getting through airport security.
I wore mine back from Cairo so I wouldn’t have to pack them. Big mistake. They’re very comfy for walking, but not so much for being trapped under the seat in front of you for the 3-hour flight to Germany, for sitting around on the terrazzo floor of the very crowded Frankfurt airport for another 6 hours, for another round of stuffed-under-the seat for the 8 or so hours of the flight back to the US, for 3 hours or so of unexpected layover in DC, then for the weather-hindered 2-hour-long flight back to Charlotte.
Next time, I will duct tape them to the outside of my luggage if there’s no room inside for them. 
Wow, almost no reason to sit on the terrazzo floor of Frankfurt airport for 6 hours. Were you in or outside of security? There is whole level, subterranean, of that airport that has restaurants, pubs, shopping, even a disco and porn shop tucked in there (disco may have gone away). For a six hour wait I’d have gone out through security. Hope this was for a flight delay of some sort, but even then there are places to sit and have a beer or coffee or whatever. On flight delays I try to find someone with some pull and get them to comp me into the frequent flyer lounge. One of the Lufthansa lounges in Frankfurt has several electronic massage chairs, which beats the hell out of sitting on the floor.
Great … now you tell me.
I second the hiking boot suggestion. They’re my walking shoe of choice, and I feel they’re acceptable both with long pants and shorts. On the plane, I take them off and sort of nest them together on their sides under the seat in front of me, and my feet are much more comfortable during the flight.
I wear my Merrells with just about everything and I think they look fine. Very comfortable too and great for a lot of walking.
I think classic topsiders are fine with both. Or mandals, if you’re into that sort of thing.
These are what I mentioned above. I’ve worn them nearly every day for two and a half years, and they’ve been round the world once, halfway round the world four times, and they’re still going strong. Light, very comfy, durable. Can’t recommend them highly enough. (Didn’t realise until just now that they’re “Euro” anything.)
Tennis shoes? Some brands like New Balance make walking-specific shoes that could be comfortable. I’m only suggesting sneakers because I can’t help but think wearing any sort of boot + shorts is horrid. Sandals might look better than sneakers but I wouldn’t want to walk forever in flip flops.
Or you can get yourself any pair of Keen’s and enjoy excellent grip and phenomenal comfort. They have some mandals, some semi-mandals, and some actual shoes.
Privos that are flats like this pair. I have three pairs and I can walk in them all day. They are by far one of the most comfortable shoes that I own that look good with jeans and probably shorts.