Much as it pains me to admit it, the best racing shorts I ever bought were also the most expensive:)

I have a pair of Assos bibs, which are still really comfy after 10 years of fairly regular use on road and mountain bikes. I was always told to keep my best shorts for racing only. That worked when I was a kid but now I want to be comfy all the time LOL. They are fitted for purpose but not intended to be versatile, i.e., on the beach, or with other stuff worn beneath them. I've also used padded inserts, and synthetic ones with good results, especially riding rough roads or on stiff-framed bikes that transmit a lot of shock to your rear end!

I'm also a huge fan of Brooks leather saddles, which are superb for long-term comfort but take a bit of breaking -in and need protection from rain.

I'd certainly give up the idea of wearing swim trunks under my cycling shorts, and find a place to change at Waikiki (I live in a place- Scotland- where 20 degrees is a rare occurence....just thinking about Hawaii is as exotic as I get!) If you can fit trunks comfortably under your shorts, perhaps a smaller size might work?

These problems can appear intractable, when a minor adjustment is all that's required- trouble is, determining the correct adjustment!

-hope you can!

Well, I don't intend to try swim trunks under bike shorts again - it was just a silly experiment, though it did work, sorta.

I do plan on trying to ride with swim trunks under some kind of regular shorts periodically though. I wasn't bad the last time and so maybe my body has adjusted decently (and will continue to get better).

Today I used the bike shorts because I didn't want to risk doing too much too soon. Maybe I'll try it with regular shorts just once or twice a week and gradually increase it until (or if) I find a limit to what I can handle. I'll certainly keep wearing bike shorts when I know I'll be riding further though.

Bob

I've made some more trips without bike shorts (12.5 miles each way with an extended rest in between).

For the most part, its been fine. Normally this is wearing swim trunks (baggy) under regular shorts. When I do this, I sometimes feel I might be sort of on the edge of getting irritation, but no big deal. After such a ride I have either skipped a day riding and/or wore bike shorts on the next trip in order to minimize the chance that some very minor irritation becomes serious.

I did have on problem ride when I work regular jockey short underwear under my regular shorts. That definitely caused some irritation! Guess I need to find different underwear for trips where I won't be wearing swim trunks.

Today I tried something new. I had rested yesterday and since I had that problem ride the day before, I decided to use the bike shorts. Once at the beach, I changed to swim trunks. When I came home, I just wore the swim trunks home. Seemed to work okay, at least for that distance.

Bob