Can I wear short shorts in downtown San Jose.?

It depends if you plan to wear the women's short shorts traditionally (on the lower part of your torso) or on your head.

You can walk around naked, but get ready for the paddy wagon to come and pick you up.

You’ll be better off further north, say San Francisco, or maybe Santa Cruz.

You can do this anywhere, but in San Francisco and Santa Cruz it won’t provoke ... say violence or negativity the way it might somewhere else.

I am in Santa Cruz and we are pretty tolerant.  I was an art vendor at a large beach glass show a couple weeks ago and a young man came into my book wearing a lovely shade of lipstick.  I started chatting with him and realized he was fully made up, and had done a great job with it.  Looked like a professional had done it. He was visiting the area and as we talked he got more comfortable with me and he got more animated I noticed while he was gesturing that he was carrying a purse that may have been little mermaid themed, like a tween girls sort of strapless handbag.  He was lovely and I hope to run into him again, we had a very interesting and wide ranging conversation.

Only Mondays, Wednesdays and Fridays between 1PM and 4PM

Who's going to stop you? Wearing shorts is protected by the First Amendment.

You can, but will look rather foolish, most guys wear longer shorts

You might find San Francisco more hospitable to your orientation.

Yes, but in certain circumstances. If you're walking around the town during the day it's fine, but for any evening or dinner engagements I'd say no, unless it's an establishment geared to an aesthetic featuring minimalist clothing.

Sure. San Jose is pretty close to San Francisco.