I own an Away carry-on (both US and international sizes) for trips under a week, and a North Face Rolling Thunder for longer trips. I purchased the Away The Everywhere Bag as a personal item, as I travel to South America where airlines can be strict about size. I wanted something professional but not too fancy to worry about shoving under an economy seat. A strap to attach it to my luggage handle was also essential. (FYI - it works great on my Away carry-on, but the North Face's weight distribution is problematic when tilted for carrying; I have to use the included strap to attach it to the side.)
My issue is that during a 5-hour layover in Boston, with our checked luggage forwarded, I was stuck carrying the messenger bag around town. It held my MacBook and gave me a sore neck/shoulder because it's not designed for extended walking. Can you suggest a backpack that can carry essentials for a long-haul flight, such as chargers, an iPad, a hoodie, pills, and some toiletries? Preferably something nice enough to be for business, but comfortable enough for use as a day pack. Also must be able to squish into most non-us personal item checks (maybe not RyanAir).