Second the suggestion of NewEnough.com — great site. Cruise through the closeouts, and get on their mailing list.
For gear, I’ve gone a different route. I’ve got the jacket(s), gloves (several weights), helmet (and ear plugs and glasses), two pair of boots (full and low-top), but for pants I go two ways. I’ve got some full A* overpants for colder rides, and for commuting and warm rides I’ve been going with Riggs Wear Ranger pants. They’re kind of like Carhartt’s, but better looking for that not-so-construction-site look, and they’re cargo pants made from cordura — the same stuff that most textile riding gear is made from. And at $33 each at DenimExpress.com, that’s a TON cheaper than most any riding pants out there. Add some knee/shin armor, and you’re set.
Maybe that will help some.