“But what about dressier fancy-pants clothes for going out at night to the club? I wanna look sharp for the ladies/men who might want to come back to the room with me and get our freak on.”
The above mentality is one that you’ll have to break to some extent if this method of traveling is going to work for you.
First of all (and most of you will realize this as you get older), very few strangers really care about your appearance, especially when you’re an obvious foreigner on vacation. So get over it.
Second, if you take care of the things that really matter, the clothes you wear out at night will be of much less significance in how your evening goes.
Years ago, I went on a tour in Europe, and we had a handful of Australian guys in our group who did very well with the ladies.
Very well with the ladies.
None of them wore anything fancier than a t-shirt the entire time, and most days their shirts didn’t even have sleeves. One guy wore jean shorts about every other day. That’s right: jean shorts.
Why did they do well with the ladies? Because they were all in great physical shape, had huge muscles from lifting weights, and were a ton of fun to be around. Put someone like that next to a scrawny, unconfident weakling with a caved in chest wearing a baller $200 button up shirt, and who do you think the ladies are going to gravitate to?
Do you really think the shirt is the game changer in this situation? Exactly. You want to hook up on vacation, forget about the expensive designer shirt and the shoes made out of reptilian integument and go hit the weights.
Third: in a pinch, what’s already in your bag can be dressy enough for most situations. See the Lacoste Sport polos in my packing list? Those are nice collared shirts, which when paired with some clean dark jeans, a belt, and shoes/sandals, will pass muster in most situations.
I haven’t taken any dress clothes on vacation in at least ten years. I’m on vacation. The last thing I want to do is wear a suit or something that even closely resembles what I wear to work every day.
Now, if this just isn’t gonna work for you, the beauty of packing light is that you likely still have lots of room in your luggage. My own personal bag during most vacations is filled to only half capacity. So if you absolutely have to, then throw a nice button up long sleeve shirt in there if it makes you feel better.
But remember: you likely won’t see any of these people ever again. If you’re a little under dressed, no one really cares other than you. So don’t worry about it.