<<My options are 10/4 - 10/18, 10/11 - 10/25, or 11/8 - 11/22? I don't want to go when it's too cold either so I'm wondering if Nov will be too cold. Will there even be a difference these 3 choices?>>

Pesonally, I'd opt for November if I were in your shoe. Yes, it'll be a bit chilly in early mornings and evening-to-night hours. But I guess you'll be quite able to enjoy autumn colors in Kyoto. October may perhaps be a bit hot here for people during daytime. Um, not sure, but could possibly be right when I say that if you minus the trade wind factor from the weather during the Jan-Mar period in Hawaii Islands will be it.

I agree with Shot. The later in the year, the better.

So what kind of clothing are we talking about? Pants and a light jacket? Would it be too cold for shorts in the day time?

for someone from Hawaii, it'll be very cool in November. Average high for the WHOLE monthin Kyoto is 62F.

I'd say in the early-to-mid November the highs are usually a bit, or sometimes well, over 20C, that is, 68F. Some people wear light winter jackets / sweater, others T-shirts. Shorts are pretty uncommon at around that period among adult males.

Shorts at that time of the year, will peg you as hen (strange), although if you're out jogging and obviously in a state of working out, that should be fine.

Adults, in general, don't wear shorts except for on weekends in the summer. Young adults, perhaps, but it's rare. I wear them if the weather permits but I do get stared at until I stare back.:-)

So I'm guessing in Oct shorts wouldn't be ok either? So no shorts for men, but what about women? Are shorts or a dress ok?

Am not a fashion advisor in my own right, but I guess fashionable shorts for ladies are quite alright. Maybe they can dress the way they want.

But frankly, I've got something on my mind: well, I don’t mean to wave a banner in favor of dress code for anyone, nor do I wish to put off any one of you on TA by saying this: I’m aware these days of there being young Japanese ladies in particular, favoring shorts-like stuff over skirts regardless of the season. That’s fine. They don’t walk on the street with flip-flops or low-cut necklines as in summer anyway. But some of them wear low-rise pants for a change, not caring a hang about revealing their cute bellybuttons even in dead winter. No rants about it, but I’m a bit on the conservative side admittedly. Um, personally, rarely did I observe any of their counterparts doing the same on Kalakaua / Kuhio Avenue in Honolulu. You know many, if not most, people tend to get fashion-conscious in their own territories, in that clothing that may turn heads may turn on tongues among fellow workers in the workplace, regardless of where you are. Yes, I think I know I’ll be swept away with the old guard: hey, you’re on vacation and can kick up your heels a bit.

I would suggest three quater capri style pants for women or three quater styled cargo pants for men. T/shirts definitely no single/shoe string tops, nothing tight fitting nor clevage revealing.

Good walking shoes and light jacket for afternoon evening.

For an evening outing, something a little more dressy.

We took shorts during our trip and would have been too embarrassed to wear them...moreso out of respect

Thank you all for your insight. I will make sure to dress warm and conservative.