If the shoe fits, then wear it, unless it's uncomfortable.
Working in a running shoe store has taught me that everyone has different feet and each shoe will fit them differently. And my mother has ingrained in me the need for comfortable, high-quality shoes.
I haven't had much luck with cheap shoes. I rarely find them comfortable and if I end up going home with them, I might wear then 2-3 times before giving them away because I end up limping or going barefoot by the end of the day. That's happened with two pairs of shoes that I can remember and it was a total waste of the money.So that's left me with a habit of buying higher-quality (and more expensive) shoes. (Sorry bank account.)
Currently I'm on the hunt for a new pair of nude heels. I've about worn mine into the ground and while they're the 2nd most comfortable heels I've owned, they're a bit narrow on me. My toes are a little long so where the outside of the shoe curves near the toes, it can be a bit tight on me. And my feet are a little wide, not wide enough to NEED a wide pair of shoes, but frequently it makes a difference.
So I took a few different pairs of heels that I liked, including the ones I already owned, printed out their pictures from the website, (I used the same website and chose the same angle- from above) and placed the papers over each other.
That showed me that the shoes I wanted the most had a narrower and pointier toe than my current ones. So I chose two pairs that had slightly rounder and wider toes (and are supposed to be comfortable brands.)
Once they arrived at my house I tried the two new pairs on along with a new pair of Corso Comos I've had sitting in their box for a couple of months, to see how each one ranked.
The Corso Como Del Pumps, while I love them, aren't the best shape for my foot. They're narrower than the other two pairs and squeeze the front of my foot. I have worn my old pair a lot, but I'm going to try out a different pair now. When I tried on the new pair of Corso Comos and compared them to another pair of new heels, I knew that the Corso Comos wouldn't continue to work.
The Trotters Signature Gigi Round Toe Pumps were supposed to be comfortable but to me they weren't comfortable at all. They didn't have much padding and I knew right away that they weren't the shoe for me. But they have a reputation for comfort so other women with different feet probably have more luck with them. It'd be worth it for me to try another pair or two of their shoes to compare comfort-wise.
The Clarks Delsie Bliss Pumps were the best of the bunch, I loved the padding under my foot. However they slipped a little, so I ordered a half size down. When the smaller shoe arrived I tried it on but it was so tight I could barely get my foot into it, so both sizes of the Clarks went back. I really wish that one of the sizes had worked, the padding under the foot seemed promising.
None of the three worked for me.
During my lunch break I went to Nordstrom and tried on a pair of Rockport Total Motion pumps. They were incredibly comfortable. I went down a half size to a size from what I usually wear and went up to a wide. I love the cushioning under my foot. The only thing I noticed was that the front of my foot hurt after standing a while on hard ground but overall, they're very comfortable and I'm keeping them.
Some of the factors that lead to a comfortable shoe are shoe height, foot shape, shoe shape, arch shape, arch size, and materials. If you've got a wider, boxier foot, you may not fit into those pointy-toe heels (but don't count yourself out because I didn't think that a pointy toed shoe would work for me and it ended up being the best.) Shoes are made for different types of feet, so you may have to shop around to find one that fits your foot. (Unless you're lucky and have a "sample" foot where most shoes work, or you're able to get them to work, for you. If you do I'm jealous.)
Nordstrom has great customer service and a wide range of brands. When I went in I asked about a few other brands and how they ran in width - such as Kate Spade and L.K. Bennett (I was thinking about splurging for a more expensive shoe if it was more comfortable) - but was told that both are best for "trim" feet.
The store owner of the shoe store I work at frequently recomends Cobb Hill for a "dressier" type of comfortable shoe (it's dressier than running shoes just not as fancy as "high-fashion" shoes.)
There are other great shoe stores out there to find the right shoe for you, but I've found it's hard to find a fashionable shoe that's comfortable.
Have you found a particular heel or brand to be comfortable?