Backpack vs Messenger Bag?

To preface, I like the “best bang for your buck” mentality regarding clothing, accessories, appliances, cars, etc. I don’t mind paying a sizable premium if it means getting a few more years from a purchase than the cheaper option.

That said, I’m debating on getting a leather backpack or a messenger bag for IB. What’s been your experience with each, and how much is too much to spend on one… any suggestions would be helpful. (For reference, I’m trying to spend no more than $400, but sometimes less can be better)

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I've been getting away for a while with a 15" Bellroy Totepack Duo in some sort of dark grey color scheme – they don't make this exact model anymore, but: (a) they still make similar ones; (b) I'm sure eBay / Amazon still has them.

Initial rationale: I can't stand leather bags / briefcases in all shapes or forms. The bag has a standard-issue-ThinkPad-bag vibe to it, so professional enough for me. Plus I really like the portrait orientation of it, but that's my quirkiness showing through, I reckon.

Pros:

  • Can fit all you need + extra. I typically pack my gym stuff (save for sneakers and flip flops that I store at the locker that I rent at my gym), an old thick-ish Lenovo f--ker of a laptop with a mouse and a charger thereto, a notebook, a spare shopping bag, sunglasses, a wallet, a research report to read on a weekend (which never happens, but hey no harm in trying), some other small random stuff – and there normally is still is a fair bit of free space left. I've even taken a weekend trip with it once (albeit without an aforementioned Lenovo).
  • Semi-detachable shoulder straps. Almost no visible signs of their existence when hidden. Helps A LOT to have an option to convert it into a backpack when: (a) it's is heavy for some reason (e. g. carrying a bunch of materials); and / or (b) you are more casually dressed so you might want to "dress down" the bag as well; and / or (c) you are on a bike or powerwalking.
  • Durable. I've been using mine (business) day in, day out for the past 1.5 years, and it displays no sign of wear.
  • Lots of pockets of all shapes and forms. No external pocket(s) for water, which I like – I'm not on a hike ffs. Internally, has 2 cushioned sections for laptops + another one for an iPad.
  • [Might not be relevant for you, as this feature is not present on current models.] There is a feature that helps to slim it down when you don't need all that extra space.

I don't insist on 15", it's just my laptop size. If anything, ordinary (non-Duo) 15" one might look a bit chunky, so I would've gone for a 13" myself if I could.

I know it's not the most direct answer to your question, but hope this helps anyway.

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