I prefer the Under Armour 9" original boxer jock. When I ride my commuter bike I never wear cycling shorts with a chamois. I think the Brooks leather saddle helps a lot with the comfort.

REI polyester boxers. Very comfortable.

This is the best boxer...

Thanks! I just ordered some.

Exofficio Men's Give-N-Go Sport Six-Inch Boxer Brief
https://www.amazon.com/gp/product/B0...?ie=UTF8&psc=1

Yeah they're expensive at $23/pair. They're worth it. (Fine to be fair I don't know what your financial situation is, but if you bought any bike specific clothing which you don't technically need then yes they're worth it).

They don't ride up your thigh - at least they don't on me and I have large thighs.
They last practically forever. They're way more cost efficient than previous brands which cost half as much but wore out in a year or two.
They're incredibly good at preventing chafing. I've been walking places that were a short drive to get exercise, the other day 100 feet out I realized I had put on an older pair of underwear that was chafing (wearing jeans), I turned around walked back home switched underwear and the issue went away.

They're just fantastic underwear. Only odd issue is I needed to order a size up for a good fit. And the waist band isn't 100% perfect - ever since I started working out my waist got bigger and it's fine, but I wish it was a little looser (I haven't found any pairs that are better though).

I highly recommend them. Any concerns about cost should be weighed against that they last at least twice as long as most other underwear I've owned.

I just wear padded cycle shorts. Briefs are not on the radar.

banana hammock or bust

9" BCG compression shorts from Academy

https://www.rei.com/product/859917/e...-mens-9-inseam
another vote for 9in inseam Ex Officio ~ they will ride up a bit.
I like my looser REI boxer-briefs as well. the looser-ness helps prevent them riding up.
- this is one of the more useful threads i've seen in a while.

I cannot say how well tehy'd fit other people, I imagine different leg shapes have different results, but I have the 6 inch version and it's long enough to prevent chafing, but they don't ride up - on me.