Are there a lot of moderately priced clothing shops in Oranjestad? I don't want to pack a bunch of clothing and then not wear it when I get there. So if there is a great place to shop there I will be able to buy something if I need it, right?

Oranjestad is the best place on Aruba for clothes shopping, but I'd say you might have find it a bit of a chore to find moderately priced stuff. Because it's known for the shopping, there are a lot of big brand stores and the small stores can afford to be higher priced, but of course, there are always exceptions...and sales.

I'd say that you practice the skill of bargaining. It is normal for the locals to raise the prices for tourists but if you know how to deal with them then you may get cheap prices for the clothes you want to buy.

I don't think I'd bank on finding a ton of deals and not bringing many clothes with you. I would think that it being an Island, you wouldn't find any cheaper stores. There might not be a ton of stores to choose from and they might be pricey.

When it comes to something basic like clothes, I would prefer to bring my own than purchase them in the place I visit. I would rather spend my money on things I cannot find in other places.