S.W.
I've found the price of kids' shoes to NOT be an indicator of quality. My daughter has sometimes worn inexpensive sneakers for an entire year. And then the next pair will fall apart in months. So I take my chances with mid-priced shoes and hope for the best. Luckily so far she is the kind to wear the same pair every day so I only need to spend on one pair at a time!
I spend extra for winter outerwear. In MN it's worth it. From the time my daughter was old enough to actively play outside, I've bought her name-brand snowsuits from REI. Most times she's gotten two winter's wear from each one and was never cold or wet while playing outside! Now her niece is wearing her previous ones and they are still in great shape.
I will spend a little more on dress/work shoes for me. My favorite ones have lasted for years. And suits (when my job has required them) that are classic and can be work often.
I calculate value by taking into account frequency of use. In other words, an expensive item isn't expensive when divided by the times it is used. I try not to spend much on an item of clothing I'll rarely wear, or any item I'll infrequently use.