There's being poor, and then there are attitudes about the poor. Modern society hasn't exactly figured out the appropriate attitude, and neither did medieval society. By modern standards, all medieval people were poor, lacking the material goods we take for granted, but people then didn't think so. This meant those who considered themselves wealthy or at least well off had to decide what to think about poor people.
For starters, medieval people couldn't decide whether poverty was a sign of holiness or the result of sin. As I discussed earlier, voluntary poverty was considered very holy in the late Roman Empire and in the High Middle Ages, times of (relative) economic prosperity and wealth, when renouncing wealth was a sign of devotion to God. After all, the New Testament depicts Jesus as without possessions or even a house. Many twelfth-century churches deliberately sought to be simple and undecorated--but not all, showing the basic division of opinion. Saint Francis in the thirteenth century said he was wed to Lady Poverty.
But even at other times (the early and late Middle Ages), when life was a lot tougher for a lot more people and holiness became equated with wealth, poor people were not automatically spurned. Although theologically it made sense that poverty was a product of sin, this did not mean then that poor people were specifically sinful. Rather, Original Sin, everybody's sinful nature, meant that there was poverty in the world. (Original Sin is a great explanation for all sorts of things.) "The poor we have always with us," says the Bible. This meant the wealthy were always responsible for trying to help them.
Giving alms, helping the poor, was considered a religious duty. Both laypeople and churches sought to help poor people. The wealthy in lay society and those monasteries that did not go in for extreme simplicity themselves would distribute leftover food at the back door after every meal. The poor did especially well if there was a feast.
Some monasteries had what were essentially official poor people, those who were fed daily, got new clothes once or twice a year, and had their feet washed on Maundy Thursday. In all of this, the emphasis was not on the poor people themselves. The emphasis was on the wealthy or comfortable. It was their Christian responsibility to help poor people, which meant they would establish official poor folks living nearby if they had to, so that they could help them.
There was still ambiguity about poor people. Sure, you were supposed to help them, but suppose they were scary and dangerous? Dirty, unkempt people are always scary, and it's easy to be dirty and unkempt if you have nowhere decent to sleep, no good clothes, and no way to bathe. And yet the scariest people were not the poor but the powerful. A knight might be clean and well-dressed, but he also had a sword and a short temper. Overall, the poor were those to be pitied and helped.
Things changed in the fourteenth century, when over-population and a string of bad harvests (always a bad combination) led to famine. Now there were a lot of poor people, most of whom were poor not for religious reasons but because they had lost their livelihood. Their numbers overwhelmed the charities that had supported the poor for the last few centuries--after all, they too now had less food to distribute.
Really for the first time the well to do started making distinctions between the "deserving" and "undeserving" poor, those who deserved to be helped and those who didn't. Thieves and bandits could be easily classified as undeserving, even if they'd stolen only to keep from starving. Children with big eyes got to be deserving.
The twenty-first century has the fourteenth century's distinction between deserving and undeserving poor. But we draw the line somewhat differently. The fourteenth century wanted to know if the poor people being helped were moral people. Today the concern is that they not be goof-offs. There is a very strong assumption that many poor people choose poverty so that they can avoid work and get freebies, which is why they have to be very carefully vetted before receiving benefits, and food stamps can't be spent on certain foods that they "don't deserve." Many would change their attitude if they suddenly had nothing.