pseudoswede

How about a messenger bag? I love my Timbuk2. I also have a Tumi that is a bit smaller.

recasun

I use 24-hour brief, and it's the most convenient for me anyway, and your variant is ok too, the most I like is sand colour

MtlTourist

I love my Nomad Lane Bento Bag! Was looking for a clamshell design and something that would fit under almost every airline seat/use as a personal item. At 8" x 10" x 17" it fits the bill. Price is steep though (about $300 US) but was worth it. I use it for flying or short weekend trips.
I bought mine back in August 2022 right before they stopped including the built in USB cable you can connect a charger to, and they also stopped including the toiletry bag and tech bag. Cost-cutting savings I guess...

gadget

Here I am, nearly a year and some experiments later. Over the last year, I've used a few different bags as a personal item. My normal Tumi briefcase has some great features with the magnetic pouches, but won't stand upright and overall is too limiting to use as a 'seat companion'. Fine for the office, not for travel. I bought a cheap 'bucket' bag, to try out that form factor. I really like it, but a single cavernous space is not what I want. I end up searching for things too much. I need more separation.

My requirements, I've concluded, are:

• Must fit RyanAir size limits for the free bag (40x20x25cm / 16x8x10")
• Immediate access (meaning: no more than one zipper, zero searching ... part of that is discipline, I realize) to: laptop, liquids, passport, wallet, keys, phone, power bank.
• Secondary space is fine. I'd load that up with things I won't load into a checked bag but am probably not going to need during transit. Things like a charger, my electric toothbrush, medikit, etc.
• The bucket space .... a big space I'd use differently depending on my travel. Short trips maybe a change of clothes, long lights I'd pack it with snacks.
• Elegant design. Black.

gadget

A new version has come out in 2023. It looks fantastic and I'm really lusting for it.

Could you comment on my two main concerns:
1) It is billed as a structured bag. I fly RyanAir regularly and the bag is 3cm/1.25" too long for their free bag policy. This could lead to expensive gate check fees, I've seen it happen before. Can the bag be compressed by as much, or will the structural elements prevent this?
2) How cavernous is that back space? On short flights, I'd use that space to pack some clothes or random things. On long flights, I'd pack it with plastic boxes containing healthy snacks and stuff.

Given my location (Thailand), I can't really try this bag out before I buy it. So I'm trying to reduce my risk in asking a friend to carry one over.

Heyden

I prefer a small vertical messenger bag as a personal item. It's small so never gets challenged. It goes under the seat with enough room for my feet and if it's not too stuffed can fit into the seat pocket. Carries tablet, phone, meds, cables and other essentials.

Dapper Dandy

I know I'm late to respond to this, but in case others are looking for something like this, I really like the Waterfield Air Duffel Carry-On as my underseat personal item. It's not the biggest, but you can cram it full, and it's one of the only items I could find which fit some off the more restrictive airline requirements for under-seat. I like the organization and it's well-built, but admittedly it's expensive.