I used the last week to intensely play Shen. I really like to play a tank which can contribute so much to the team (his Taunt and Ult are just awesome).
I usually play him on Top lane where I face mostly Bruisers and Tanks.
So when I play against them I sustain my lane, try to harass with my Q (Vorpal Blade) and farm. When they overextend, I try to punish it, but altogether I think Shen is not offensive enough to gank alone. So I prefer to gank my enemy when the jungler shows up.
This works very well against melee champs like Xin Zhao, Shen or Nautilus.
Now when I play against a ranged carry on top I really tend to fail. For example, I can't do anything versus a Teemo. All I can do is try to safely farm with my Q. If I try anything else, he goes for me, and I am not quite sure what I can do about it. I can't bring do burst damage to him since Shen has no burst.
For example when I play Riven (my main char) versus Teemo (or another ranged carry) I wait for them to overextend a bit and then go in, do some real damage and go out. But with Shen this is just not possible.
So any advice?
Best Answer
You could take the game to them and be aggressive. A nice combo that I like to use is dash (into them to taunt them) -> vaporal blade -> shield -> auto-attack until vaporal blade goes out, and than back up into safety. It's kind of what you are already doing with Riven. Ranged champs are squishy, and this way you can burst enough damage to them to make them think twice before coming within your range next time. It is also very nice because you can get into their face from a distance (considering Shen is a melee champion, this is a very useful). Whenever you see them coming close to you, punish them with this combo. You just need to make sure you have enough energy to cast all three skills, and not initiate if you see you don't have enough.
If you see that they are still stronger than you, and that you still receive more damage than you deal to them, and if they're playing aggressively then just hug your tower and last hit (help yourself in this using vaporal blade). When they are in range of the tower, taunt them with dash so tower starts attacking them.
Also make sure to regain your hp with vaporal blade whenever you can (without sacrificing more hp), and a good thing is also to start with doran's shield.