I was wondering if anyone could shed some light?!
I'm planning to go on a backpacking trip (~3-4 months?) in a couple years and after doing research on all sorts of bags, I want to make a Filson my companion.
1) I don't want to look like a backpacker
2) Those colourful traveller backpacks are really ugly and draw in the thieves and gypsies / trigger the vendors to inflate prices for me
3) I own a Filson and I know it can take a battering + look beautiful
4) I am a sucker for patina, lol
I'll be travelling light (few shirts, jeans, a couple shorts, a few pairs of underwear and some disposable underwear, waterproof shell) think 4-5 day trip with more essentials.
I want a bag I can carry-on (total <45 inches) so I can save time at airports.
I'll be wearing it as a backpack too:

Small duffle.
It sounds like a dumb idea but it's not as uncomfortable as it looks.
I WILL find a way to get custom backpack straps that will be attachable to the metal D-rings on the sides where the shoulder strap attaches to.
Narrowed it down to:
Small Duffle (39 inches)
Medium Duffle (52 inches)
Medium Travel Bag (42 inches)
I've read that the Medium Duffle can pass as a carry-on if not filled to capacity, anyone have first-hand experience?
Or any other recommendations? If only the duffle came in a size between the S and M!
I'm thinking that the small duffle will be too small, the medium duffle won't pass as a carry-on and the D-rings on the M travel bag are too low for me to install backpack straps onto. (see photo below)
Duffle

Travel bag

Sorry for the essay, any help is appreciated!
