How about putting a 2x5 shrouded male header recessed in the enclosure and a 2x5 female IDC connector on a ribbon cable? It can be a bit difficult to remove so might not be ideal if it's something that will be constantly plugged/unplugged but on the other hand it is unlikely to come loose. If you use the IDE connectors with strain relief it gives a bit more female connector to grab on to.
I haven't looked for the male headers in a panel mount form but you could design your project and enclosure so that the PCB mount ones are positioned correctly, they have right angle ones also if that works better.
pert:
you could design your project and enclosure so that the PCB mount ones are positioned correctly, they have right angle ones also if that works better.
What I mean is that the male header is soldered to a circuit board, this provides the mount. The box has a slot cut out in the shape of the shroud and the circuit board is mounted in the box so that the shroud is correctly aligned with the slot in the box.
There are many other options but I try to use IDC+ribbon cable or dupont for all my cabling needs because they are very standard, cheap, and easy to work with once you have the tools. RJ45 cables are cheap but all the PCB mount jacks I've seen aren't compatible with standard 0.1 inch grid.
There should be many options to meet your needs on the sites that spycatcher2k recommended. I know that digikey and mouser have a very good parametric search where you can specify the mounting type, number of connectors, termination style, and allow you to sort the results.