Bootsless Tryndamere Is Awesome
Ignore my match history because I usually suck with builds. Bootsless trondo is so much fun to play with and is also amazing!
Warlord's Bloodlust
Start/Core:
Mid/Lategame Options:

For Bad Lane MU's:
For
:
Ban or
(or don't use this build lol)
Scaling MR glyphs seem super important as do AS runes; maybe 1 lifesteal quint too.
Try it out! Have a blast!
Go ham after laning phase in no particular lane. You won't be as effective at splitting as trondo with boots but no one will want to touch you or any of your nearby teammates with a 10-foot pole. No lifesteal outside of Doran's Blade and Warlord's Bloodlust (and maybe a quint) is important for two reasons: crit items amplify tryn's damage by a metric butt-ton and him being at lower health in general means that he deals even MORE damage thanks to his Q's passive. 110% crit chance with IE+PD+Shiv is a little wasteful but so worth it as it offers you consistently impactful AoE magic damage in teamfights. BORK seems eh especially after the price nerf but imean it has a built-in gap closer and an on-hit effect...yeah, I feel less great about that lategame item than I do all the others. Maybe Maw is worth considering against heavy AP. The new GA is so obnoxious lol. Once you have IE, get it anytime you want it.