I like my cycling specific clothing, but they show their advantages best when I take a long ride, longer than ten miles. I'm specifically talking about jerseys and shorts or tights.

That's a good article about shoes, and it could be useful for many people, but cycling specific shoes are a life saver for me. I get severe foot pain when I don't ride with them, for various weird reasons. I use SPD cleats, and my favorite shoes (among my many SPD shoes) are built for mountain bike racing. They are super stiff. The soles are slightly curved, so when I stand in them, I can rock on them, which prevents fatigue. I've hiked in the woods wearing them, and their traction is good except when the cleat occasionally touches a rock, but even that isn't so bad.

My cycling hats are my most comfortable hats of all. I realize I'm breaking "the rules" when wearing one off the bike, but I don't care. I wear hats when I'm outside, as I'm going bald.