I'm curious how often you need to carry your laptop (and other things) once you land at your destination? For me, this is the reason I use a professional-looking backpack to carry my laptop and other essentials. If I didn't have that, I would end up taking my wheeled carry-on bag with me to the office and/or to visit customers, which would make me look extremely strange.

Honestly, I would recommend looking for a backpack as small as you can muster with a luggage passthrough. Mine fits under the seat in front of my in any sized plane, carries not much more than a laptop, headphones and some chargers, and I can carry it around the city or with me when I'm on the road.

For a while, I traveled with https://www.cocooninnovations.com/pr...product_id=282 which I promise nobody will describe as "big". Now I use a Tumi backpack that's a bit bigger, but still very small.