I'm following the flock on this one, a good seat and good shorts.
My shorts are partially graded for distance, with lower end shorts being used for short rides and the ones with better padding being saved for when they are most needed. I don't get the Assos out for anything under 50 miles.
In respect of saddle, I have recently switched to a Fizik Kurve Snake as it can as OEM on my new bike. Now that it is broken in, I can say that I am delighted with it, so much so I have got another on the way for the other bike. A completely different saddle concept than most, but it really works for me. If your LBS are a Fizik stockist, they might have a test saddle they could loan you for a week or two to try out. I couldn't recommend it highly enough.
Prior to the Fizik, I was using a Spesh Romin Evo Expert, it was comfy enough, but the Fizik is a world apart. The Spesh had you planted to one place where the Fizik allows you more movement and more comfort in the movement.
Most likely the Spesh will be going on
eBay when the second Kurve Snake arrives.
