AggieTexan

I just bought this TUMI Elias flap backpack at an outlet store for less than $200. It has a designated laptop pocket, plenty of space, and is very lightweight. It's similar to one you posted, but quite a bit less expensive.

TUMI Backpack

ChocolateFactory

Hmmm, that looks a bit small to me? Also it looks like it has too few pockets/compartments?

I would like the backpack to fit the following items:

- 14" laptop
- laptop charger
- small umbrella
- passport/boarding pass easily accessible (outside pocket)
- plastic bag with liquids
- iPhone charger/cables/adapters, headphones
- a book
- clothes for 2-3 days (two shirts, t-shirts, underwear, socks, a pair of jeans, etc.)
- second wallet
- credit card holder
- keys

Ideally there would be different compartments/pockets to keep things organized.
My current laptop bag actually fits all this, but then it's really stuffed and a backpack is just more practical:



So the backpack should offer a little more space than this.
Also, I no longer like the way my laptop bag looks (it just looks to much like a laptop bag) and I'd like to use the bag without a computer in it as well (which I feel is strange with a laptop bag).

frankmu

I saw this brand in Tokyo. I think you can get them here in the US. I noticed many of the younger "salary men" had cool backpacks like these.

https://www.hideowakamatsu.com/colle.../everyday-bags

Edit: sorry, I realized they don't have the pass through slots

mekut

I have been using this bag for several years. Has a wonderfully functional passthrough strap and lots of space. My main critique is water bottle holder almost worthless so I put water bottle inside.
Here's a link for photos and description
https://www.amazon.com/High-Sierra-X.../dp/B00GR7BOF0

gobluetwo

I have the Everki Versa Premium backpack. Not styled like the typical laptop backpack you dislike, but neither is it the look you want. This backpack would largely meet your needs, although the divider in the main pocket is a little inconvenient for clothes. It can be done (I've done it), though. I routinely carry all those items (aside from clothes) you describe and it works well. Added bonus of being TSA checkpoint friendly.

https://www.everki.com/products1/bac...-pro-15-detail

ryw

I use a High Sierra too, but a different model - https://www.amazon.com/High-Sierra-E...s=040176448558

Has the pass-through slot on the back.
*2 large compartments - big enough for a 14" laptop. Depending how thick your clothing is, you could probably fit in those clothes too.
*1 medium compartment - good for electronics accessories & a book
*3 smaller pockets that you could use for the passport, cards, liquids bag, wallet, keys, other accessories, etc.
* One water bottle holder (presumably you could use that to hold an umbrella). Alternatively, I'm able to stick a small collapsable umbrella in another side pocket.

One possible negative is that it's slightly tall, so if it's under the seat in front of you and you're tall it might take a couple inches of leg space that other bags wouldn't. (As a shorter person it doesn't bother me, and no problem if it's in the overhead).

Outside of professional use, I've also used it for hikes and it worked well!