I'm 32 and bought them when I was 29. I'll be the first to agree that they aren't the hippest shoe in my stable, but they're a good standby and very versatile on the casual end of the spectrum. I've rocked them with everything from a tan linen suit to flannel-lined jeans. The brown outland leather ages better than any other shoe I own so far. Disclaimer: at first I only bought them because precisely zero other goodyear-welted shoes were available on the planet with a rubber sole in size 14AA, but since then they've grown on me quite a bit.
In other news, look what came in the mail today from allaboutshoes:
They fit just fine over the thicker socks that I'd wear with boots anyway, they are absolutely flawless, and the finish matches my shell wallet perfectly.
Now I just need to put in the time and elbow grease to get their finish up to Cold Iron standards...