I've spent a couple of years trying to buy a boot that I liked. Several years ago I bought a pair Cruiserworks Men's Tour boots. They're easy to slip on, very comfortable, waterproof, but have little to no retention. I fundamentally don't feel secure on them at highway speed.
So last year I bought a pair of Sidi Champions which, while very comfortable and secure, are 1) not made of leather and didn't breathe and so that after a full day of hard riding my feet would look like prunes after a long day in the tub, and 2) are a pain in the butt to put on because the straps are on the outside of your leg.
So I read a ton of posts and articles, and today sprung for a pair of BMW Contours. I bought them at my local dealer in Plano. He did me good on the price, too. $295 with tax. After 50 or so miles today they seem darn nice. Easy to put on, secure on the bike, and comfy for walking. I'll still wear my Cruiserworks Tour boots for short hops around town, but hopefully, these BMW Contours will be my boots for the next 100,000 miles.