Start with a good quality leather overnight bag. I like ones that have the "doctor" style opening at the top.
My father gave me a great quality DOPP kit when I went on my first solo trip abroad at 18. I have had it ever since. I exchange a few items for their miniature travel versions, top up the condoms, pills etc and toss it into my bag.
I suit up (sans tie) for the flight, so I grab my
felt shoe bags, clean up my more casual shoes, put them in my shoe bags and into my luggage.
- Two pairs of sunglasses.
- Swimming shorts
- Two pairs of socks
- Three underwear
- Two pairs of slacks
- Two button ups
- Case with pocket squares, cufflinks, collar stays etc
- Polo
- Travel speakers
- Phone
- Chargers, cables etc
- Kindle
- Flask
- Zippo
- Water flask
- Camera
- Japanese style fan
- Pen and notebook
If I was hitting the road for a roadtrip then I bring a small cooler bag. Perfect for filling with ice and a few "road pops". Also a towel for hitting up the local swimming holes (one of my road trip staples). I also tend to rough it when I road trip (for the most part) so my list would be different in some regards.
This is a list for air travel.