I bought some comfortable boots from Target not that long ago. They are black Mossimo knee-high boots with a pointed toe and 2.5" spiked heels. Despite the pointy toe and spike heel they are very comfortable. I wear them all weekend long, even around the house and to church with no problem.
At Target, there are also other styles with square toes and broader heels if that would work better for you.
I just bought a pair of high heeled boots at Nordstrom last week and they're very comfortable because the heel is 4" but it has a platform so it's easier to walk in these boots. I also bought a pair of high heeled boots from Newport News that had a 3.5" heel that I wear to work occasionally. If I'm shopping on the weekends, it's more comfortable to wear a boot with a stacked heel than a stiletto heel.
I have a diificulty with selecting boots because there are so many heights and types of heels to choose from so I understand your dilemna.
I found any from Spiegel are very comfy. I own a pair of their 3 inch high heel boots and I can wear them all day. You can also find comfy ones at www.chadwicks.com Hope that helps.