My philosophy on mens travel footwear

The biggest challenge I have when packing is shoes. More generally, footwear. See my feet are size 11, double wide. For my girlfriend to throw a pair of running shoes and flip flops into the bag, well that’s a non-issue.

My Rainbow slippers next to hers. Mine feel like they are each the size of a paperback book.

I have been traveling for fun, hiking, and work, for six years now. My primary mode of travel is on the airplane, which has led me to consider the many merits of lightweight, one-bag travel. Carry-on only is the biggest goal for me. When I first started flying to Yosemite for backpacking trips, I would hem and haw and calculate and repack for hours. Sometimes packing was a six hour ordeal, broken into two sessions by a quick dinner.

[Read more about it here.  You shouldn’t have to go through the same time sink.]

My quest ultimately led me to a five step method for packing footwear. Two. Two is the maximum number of footwear to bring. One in the bag and one on your feet. If you have smaller feet, well the footwear won’t take up as much space, and then, by all means go for three. For the rest of us big footed folks, or those wanting to cut down pack size, here’s the way I think you should go.

  1. Write out all the activities you are planning to do on the trip.
    I get excited about footwear because of the potential space savings. Additionally, I think that for men, there aren’t as many cross over type footwear. For example, for a woman to wear strapless sandals, well I’ve seen people pull it off in a business casual environment. If a man wore sandals, well, you’ve got to be a pretty cool guy.  Basically you want to think about all the activities that might require special footwear. Here are some examples: hiking, walking all day, stomping through puddles, dancing, dinner at a nice restaurant, running, working out at a gym, wedding.
  2. Categorize into the three delicious efficiency categories.
    Decide if these are activities that can be done with a casual+active shoe, casual+dress shoe, or if they need a specific type of footwear. Highly personally, but the categories help. Here is an example from a trip we did to Hawaii:
    Reunion – dress or casual/dress
    Day hiking in Hawaii – active shoe
    Day to day wear in Hawaii – flip flops
    Reunions may be less formal than weddings. In Hawaii even more so, so having on dress shoes or a pair of leather shoes would be just as acceptable as a dark, closed-toed shoe. I like flip flops as day to day wear because walking around is really nice for me in flip flops because my feet are big and they get hot. If you’re not hiking as much or on as difficult and uneven terrain, then go with a casual shoe. The day hiking we did is more strenuous. I have hurt my ankle twice in my life that required 6-8 months in a boot, so I opt for more support.
  3. Check for concessions or combinations.
    Holding everything in your head is difficult [humans can only hold so much in their heads]. Thinking of every activity is easier when written out. So use the list to consider each activity. If you need footwear for a nice dinner, can you use something a little less dressy, but much more comfortable? If so, then you could use those comfortable shoes for looking nice around town. [That would be an excellent example for New York.]
  4. Consider if you can buy something there.
    If you’re planning on buying something at your destination, then take that into consideration. [Buy stuff when you get there.]
  5. Pack for the most common scenarios.
    Here is where all your hard work pays off. You look through the list and, well, now you can see what is the most common type of footwear. You can now consider if you can pull it off with one pair, but it’s most likely two.

    For the above example, I could have made a few concessions. Here are some TWO footwear solutions for a trip to [Hawaii] with a semi-formal event, hikes, and day to day:

    • Casual+dress and flip flops – a casual, black shoe that could handle hikes would have been fine at the reunion. something like a leather sneaker. This way, I could hike and go to the reunion in the same shoes. In Hawaii, it is more important to have good footwear for the harder hikes because the bar was a little lower for a reunion. Flip flops because I like wearing them so much.
    • Casual+dress and running shoes – a more dressy shoe, like a leather boot that I could wear all day, and a running shoe for using on the hikes. Compromise would be that I would wear the running shoe or casual dress shoe around most days. Going on the beach is actually fine with the casual+dress or running shoe. Take them off and throw them in your bag or carry them. Or, walk barefoot to the beach, because we stayed right by the beach.
    • One pair solution: A casual leather shoe, black or brown, that I could use for all occasions. A shoe like a vans or leather converse that I could use for all occasions. Concession would be you’d have to find something that looked reasonable, but could also hike. If you look at old backpacking photos, everyone wore leather boots. A casual leather shoe, instead of a boot, would be good because you could still slip it on and off for time at the beach.

    What I did:
    Maybe you’re the kind of person that pulls off red converse all stars at a wedding. Frankly, I’m not. I want to be wearing leather dress shoes with high polish. My cousin can have on black leather converse sneakers. He has a more casual look and it works for him. Style is about self-presentation. Good style, well you figure out what looks good on you. In a formal setting like a wedding, I like to be dressed up. I have dress shoes that I know can take some moisture. And I’ve had them fitted with a thin rubber cap. In Hawaii, I did the full trifecta: flip flops, running shoes, and dress shoes. It worked fine. But they took up a significant amount of space in my personal item. In the end, I would have liked to optimize, but I didn’t know then, what I’ve outlined above. Again it worked fine, but it was the hardest while traveling, and if we had to be more mobile, then it would have been pretty terrible. On this particular trip, I knew we were staying in one location for a few days, then staying at a friend’s house for the other four days. We would be traveling by plane and bus, but nothing too difficult or arduous. No multi-hour treks. So, the bus rides and transit of our belongings was difficult, but we still kept the bags to carry-on limits.

    I get a little neurotic about packing, and I guess this article is a good example. It would have worked if I had followed any of my 2 shoe solutions above. But I didn’t. The extra footwear minimally impacted the trip because, well, we didn’t have to move around, we didn’t have to leave anything behind, and we are young and strong and able to carry all our crap. Plus, I find an unusual feeling of satisfaction running around the airport with just a carry on bags, or walking past and around unencumbered by multiple or large rolling luggage. This thinking that has kept me up into the wee hours of the morning before a trip, all the in search of the subtle pleasure of a small, lightweight bag.


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