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I'm trying to pack for a two-week trip across three different climates, and I'm completely stuck on footwear. I can't justify checking a bag just for shoes, but I need something that can handle city walking, a possible light hike, and won't look ridiculous with dinner attire. Is it actually possible to find one pair of versatile travel shoes that does it all?

Yes, it can work. I used one pair of leather hybrid sneakers — versatile travel shoes — that look fine with a dinner outfit and still handle city walking and a light hike. They held up for most of a two week trip, but by the end the soles were getting worn and I was itching for a second pair.

I tried something similar and it felt like a compromise that never fully paid off. The shoes looked smart enough for evenings, but on a slick hill they slipped, and after a few days my feet protested the lack of a proper hiking option.

Is the real problem the dinner attire constraint?

I kept telling myself one pair would work and then ended up with a tiny backup anyway. If you force it, maybe a leather sneaker with solid tread is your best bet, but it won't be perfect on rough trails.

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