How to: Choose Traveling Shoes

You think the hardest part about travel is deciding where to go, keeping to a budget, or adjusting to a new culture? Wrong. Dead wrong. The hardest part about travel is choosing the right traveling shoes.

Seriously, this is a constant problem for me, because almost every trip I take involves a ton of walking, though not necessarily actual wilderness hiking, but they almost all involve being in cities where I’ll want to go to bars and restaurants and generally look cute, too.

Theoretically I could bring two pairs, but shoes are bulky and heavy, and when space and weight is at a premium in my backpack, I hardly want to pack an extra pair.

The first consideration is temperature. When the weather isn’t going to be too hot, I default to a pair of tall, flat black boots that I wear like a uniform at home because I like the way they look, they go with everything, and they’re comfortable enough for me to walk the length of the city in. But if I’m going to a warm climate, knee-high boots are not exactly appropriate. I used to have a pair of perfectly comfortable black flats that similarly looked good and went with everything, but I walked around in them so long that I wore holes in the soles. And because I hate shopping, and I hate clothes and shoe shopping worst of all, I haven’t found a pair to replace them yet.

I suppose I could stop being so vain about what I put on my feet, but I feel pretty strongly that wearing bulky athletic shoes, which might be comfortable for long walks, points you out as a gauche tourist. And I just can’t. I would rather have blisters and bloody feet than wear un-cute sneakers. (Although I do have one reasonably good-looking and very comfy pair of sneakers that will do for city walking and for dive bars and casual restaurants, although not for a night at the theater or fancy dinners.)

Usually, what gives is my desire for a lighter and emptier bag. I will just pack an extra pair of shoes to wear out at night or when I want to look dressier, and I’ll wear bulkier walking shoes (I don’t have a proper pair of hiking boots, but I do have some sturdy running shoes that work well) on actual travel days so I don’t have to take up too much extra room in my backpack.

The conundrum remains: barring extreme weather conditions or other outrageous circumstances (formal wedding, mountain climbing), what are the ideal shoes for traveling in? Can you ever have just one pair? Are two options always necessary?


5 thoughts on “How to: Choose Traveling Shoes

  1. Oh, I’ve learned my lesson here. I now travel with my Keens as they are all extremely comfortable, durable and packable! The classic hybrid sandals are great for light hiking, cycling, and/or kicking around town. But I especially love their ever-expanding line of shoes to include super-cute oxfords, mary janes, ballet flats, etc. As for my strappy high heels…? Oh, they rarely get worn but go along as well—packed neatly on top.

  2. My fellow cuBe farm inhabitant, I loved your essay on shoes. one pair of shoes? No way, dress shoes (loafers) plus Tevas, plus Your walking shoes. Of course I do not travel with shoes in my backpack and I don’t do wilderness and I never wear sneakers. I am talking cities and hopefully much warmer than Chicago. Miami or San Juan… Wm

    Sent from my iPad

    • Wait… if you don’t travel with shoes in your backpack, do you wear three pairs of shoes at a time? I’m so confused. I’d love to carry three kinds of shoes with me, but I have no idea how I’d fit them in my bag and still not check luggage.

  3. I used to worry about this but now i wear my birkenstock sandals during the day and deal with the fact that i look like a butch tourist – they are way too comfy and durable to not wear! I also bring some smart pumps for going out and some pretty T-bar sandals if i dont have to walk far. Men definitely have it easier in this department!

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