i'll give another testimonial for Seat Concepts.
Like old-n-slo, I've found a good combination of pants and underwear to keep my butt happy. My other bike is a Honda ST1300 and I've put in lots of 600+ mile days in a row on it. My butt is not made of iron. I found that, for summer riding, Duluth Trading Buck Naked Boxer Briefs
do a good job of keeping the floppy bits in place and offering excellent ventilation with no adhesion. In fact, they're so comfortable I swapped out all of my cotton boxers and now only wear the Buck Nakeds, and have found that their Free Range cotton variety makes for good winter wear. They make women's versions too.
But for the Sherpa, the seat upgrade was mandatory. No clothing would make my butt happy on the stock seat for more than 50 miles. Unlike old-n-slo, one big problem I had with the seat was that it's so slippery. The boys were being way too well acquainted with the gas tank every time I hit the brake. Seat concepts offers several different kinds of vinyl and I got the "Gripper" style for the top cover. Not my butt stays where I put it and I like it like that.
On a side note, they call one of their vinyl choices "carbon fiber style" or something like that. I am no fan of fake carbon fiber. It ain't fooling anyone, especially on a flexible surface. What they call carbon fiber turns out to be a finely-textured basket weave patterned embossed vinyl. Very acceptable. That's the finish on the side panels of my Seat Concepts saddle and it's not cheesy at all.
It all comes down to personal preference. It's your butt so it's up to you to find the right combination of clothing and seat to get through the miles. At $170, Seat Concepts is a lot cheaper than most other custom seat options (and there are few production upgrades available for our little guys) and for me, it's been the best mod for the buck.