Indispensable items I never leave for the airport without:
iPad +home-made kneeboard (cheap ipad case with elastic/velcro stitched to it)
Bose A20 Headset (I had to use my old DCs for a flight when the cable was being replaced, and my god what a difference it makes)
Torch (even if you only fly by day, remember if you land before sunset the light will go rapido at this time of year)
Sunglasses (essential especially in winter with low sun at almost all times)
I have a standard vaguely expensive backpack rather than some whizzo flight bag, as they are a chronic waste of money (though it turns out my old flight bag is a very good overnight/carry on bag if flying Ryanair).
Lifejacket - almost always worn.
Lifejacket - almost always worn.
Even over land?
Never fly without Bose X headset, iCom and torch, A5 kneeboard (A4 utterly useless! :-) )
Also utterly useless but seemed a good idea at the time: Circuit (pattern) calculator. I don't think I have ever met anybody who fell for that one. Well, they saw me coming . . . :-(
Certainly one of the best things that I ever bought was a set of sunglasses with a small reading lens at the bottom. Just by glancing through a small area at the bottom my ageing eyes can check the chart or read the altimeter sub scale without waiting for the vision to adapt.
The daftest thing that I bought was a baseball cap to fly in. When I kicked into a goodly sideslip the wind under the peak removed hat and headset, a bit distracting and a lesson learned.
Most annoying bit of kit is a Transair flight bag that is slightly shorter than a standard 1/500,000 ruler when stowed diagonally across the bag, and which has end-bags slightly too small to hold a headset, and which has plastic clasps which are slightly too weak, and break.
I came across this old thread randomly and thought it is quite interesting in how people who own planes manage to avoid carrying anything that is useless.
I only have a small bag, so headset, ipad, kneeboard, maps in the main pocket and front pocket full of pens, torch, knife, cigarette lighter charger, chequebook, keys. It was my grandfather’s hand luggage bag so it’s used for sentimental reasons rather than anything else.
It’s perfectly organised and tidy when I leave home but as soon as I’m in the plane it instantly becomes a mess 
Sunglasses and cap a permanent fixture
Most of the time I only carry the Bose A20 headset bag where the back pouch holds my papers (licence, medical, passport if needed) and two good pens. Inside spare batteries, a cheapo ebay led flashlight and an Apple charging cable. For IFR and longer-ish flights I bring my basic Pooleys kneeboard as well (the aluminum plate with a velcro strap). The iPhone is always in my pocket.
My first 100 FHs I always brought the Jeppesen flight bag with a full set of charts, rulers, calculators etc……… probably 20 kgs worth.
I used to carry my flying bits and pieces in an old freebie laptop bag, and the headsets I carried separately in the cases they came with. Of course this meant that when going away overnight I had to carry another bag, which I didn’t like.
I changed this setup maybe a year ago when I bought an actual flying bag! I know, terrible!
But it’s pretty good. It’s essentially a small holdall which is absolutely festooned with outside pockets and has a headset-type pocket on each end. The outside pockets and one end pocket hold all my flying things: tablet, license and logbook, aeroplane keys, pens and pencils, torch, penknife, kneeboard (A5 folding), chart, high-viz, any other paperwork etc. The other end pocket holds my spare (David Clark) headset in its soft case. The main compartment just holds my Zulu 2 headset in its hard case and anything else random I need that day, plus wallet, keys and phone. My flying sunglasses (Aviators, what else?!) live in a soft pouch in the Zulu case along with spare batteries. If I’m away overnight then I carry the Zulu case separately (and of course it can stay in the aeroplane whilst at destination) and the main compartment becomes my overnight bag – clothes and washbag.
For me this solved the problem of what stays in the plane and what comes with me when I’m overnighting somewhere. The headsets stay, everything else comes with. Before I was leaving my flight bag in the plane to avoid carrying two bags, but having to transfer anything I might need for off-airport planning (chart, tablet) to the overnight bag.
In the luggage compartment of the TB10 shareoplane lives a plastic tote box containing 2x spare headsets for rear seat pax, chocks, a couple of 1L containers of engine oil, cloths, glass cleaner, a few basic tools etc.
