Updated: Oct 17
No one cares how you look when you travel... no one but you that is; it's a lesson I learned the hard way after prepping for a year-long trip, and making the mistake of packing casual shoes, hiking shoes, dress shoes, nice jeans and a beautiful, elegant button-down shirt.
But the problem was.. I never wore them.. like.. ever.
Yes, I went out on the town, yes, I went to plenty of bars and even the occasional club, but I didn't get a second look wearing my generic, black trail-running shoes, hiking shorts and quick-dry t-shirts.
No one cared... not my travel mates, not the doormen, not the bartenders, not even members of the opposite sex I was purportedly trying to impress.. (or at least, give off some semblance of style).
The truth is, no one cares what you look like when you're traveling, yes, you may not want to look like a hiker when you're out on the town in your home city/state, but the second you step off that plane in another country, none of the same rules apply.
To the locals, you already look weird - whether by the tone of your skin or the constant look of confusion on your face - everyone knows you're "from out of town;" and to the travelers you meet on the road.. guess what, they're not in their Sunday best either.
Especially if you're traveling long-term, you're likely hitting countries and off-the-wall places that have no idea what a "typical American" wears; you stand out because you're traveling, and that's it.
I remember once, getting a long, curious look as I was checking into a nice hotel for a one-night, pamper-myself-stay after three weeks in a shared hostel.. the receptionist was eyeing me up and down, at first I thought she was judging me for my overly-casual attire.. but it turns out, she'd just never heard of Nike, so she was eying the symbol on my shirt.
That's about the worst you'll run into when you're traveling, and frankly, if you get judged by a fellow American for being the least stylish person on the planet, you probably don't want to hang out with them anyway.
I'll fully admit that I cared way too much about how I looked before hitting the road, only to learn that all my careful style-conscious planning was a waste, and perhaps this is common knowledge, but if you're trying to pack for every possible occasion, learn from my mistake, and leave the fancy stuff at home.