As some of you already know, I'll be in India the first two weeks of December (Delhi, Jaipur, Agra, Orchha, Khajuraho, Varanasi). I'm starting to think about what I should take. From my research, it looks like the weather will be ideal and I'm wondering if I'll be cold in the evening with sport sandals. I was hoping to limit myself to a single pair of shoes.
Also, is a rolling bag useless? I'm thinking the sidewalks will likely be uneven and maybe a backpack or something similar might be better. Thoughts?

Also, suggestions on clothing? I like to travel light and am assuming to plan on layering. Casual clothes?

Yes, bringing clothing which you can layer is ideal, as temps will go up and down during the day. A shawl is a very useful item (you can buy many lovely ones in India, so you might want to wait until you arrive). A cotton or light wool sweater/twin set, and/or a wool blazer are useful as well. A lined windbreaker or safari jacket might be useful.

I would throw in a wool or other warm hat and a pair of gloves, for early mornings at the Taj and Varanasi. They take up no room and can come in quite handy. Bring thick warm socks for the many places you have to remove shoes but still want your feet to be warm (and stay clean). Marble is quite cold (e.g., the Taj at sunrise).

I would say everything is quite casual, the one exception might be if you went to a very nice restaurant in a 5 star hotel. You could still wear trousers and a casual shirt, but the women around you may be dressed up in spangled saris and jewelry. So it’s up to you. A colourful silk scarf may be just enough in that situation, and is easy to pack.

As far as shoes, you can always wear socks with the sandals if you feel cold (assuming you are OK looking like a German tourist), but I would note that the local may be quite bundled up, esp. at night, and you may feel a little odd with your bare feet in sandals. It’s winter to them. But up to you. I also find the streets quite dusty and dirty and your feet would tend to get dirty with open shoes and no socks. If you have or can get something like Merrell’s closed walking shoes, those may be better.

Rolling suitcases are OK, you can roll them along in train stations if you want (although you will be inundated with porter offers and it is definitely worth the 20 Rupees). The airports all have free luggage carts so the rolling suitcase is not really necessary. I don’t know how much “walking” with your luggage you will be doing on city streets anyway. It’s not like one would be able to walk from the train station to your hotel in any of the places on your itin. Or from the airport. I believe you will be on a tour, so you will handle your luggage even less than someone who is travelling on their own. So I would say to bring whatever you want. I wouldn’t buy a special suitcase just for this trip.

I would definitely take two pairs of footwear, if only to give your feet a rest from one pair. And if you're doing any walking to speak of on North Indian sidewalks you'll be happier with more protection rather than less. You need to worry about dirt and about uneven surfaces (to put it politely - watch out for gaping holes!).

Maybe I'll take my Merrell's clogs. They are very comfortable and might be better than the sandals. Or maybe I'll take both and will then be set. I could wear the clogs on the plane - the sandals are fairly lightweight and I could pack them.

Regarding the luggage, even though I'll be with a tour group, you're expected to handle your own luggage for the most part, I believe (it's a grassroots kind of tour). Still, it sounds like the rolling luggage might work. I only take a 22-inch carry-on, so it's not that difficult to maneuver.

Thanks!

Is that Intrepid you're traveling with? Is it a Comfort level? Because if not you might find it easier with a backpack.

Yes, it's Intrepid, and yes it's a comfort level. Do they handle the luggage for you on a comfort level trip? I thought the only difference between comfort and classic was nicer hotels and a flight rather than overnight train.

No, they don't handle the luggage for you, but you may be on private rather than public transport. I did Comfort Morocco and we had a private mini-coach aside from one train trip. On Asian Basix level you're usually on trains, buses, shared taxis, etc. etc. where soft-sided packs are more likely to fit and easier to schlep.