Always. It's always pertinent to keep an eye on the job market. I look every few months, not because I want another job, but because it's good to know what the going rates/conditions for similar positions are, how much work is out there, etc. It gives you a good a good feel for whether you're getting a good deal.
You'll find that if you're happy in your current job and you're getting a reasonable deal then nothing will really jump out of the job ads at you.
If you find a job you think will be better than your current one then apply for it; be mindful that if you have long term stable employment and you move on you might actually lose conditions that you've managed build up over time (flexible hours, more leave than is normal, etc).