"When to lend or not lend your clothes/shoes to friends, family, coworkers?"
Here is what I base it on:
1. Person [aka Friendship Status]: I think, 'how well do they take care of their OWN clothes?' 'Have I lent them something in the past and they returned it in the same condition that I lent it to them in?' 'How do they wash their clothes?' 'Where are they going to be wearing this item to?' 'How close am I to this person?' 'Do I trust them?'
2. Cost: How much does the item cost? How rare is the item? If the person was to wreck or lose the item will they be able to afford to buy you a replacement? Are you even able to replace the item?
3. Location: How far does this person live from you? This will determine when you can expect to get the item back. Is the store that you bought it from in the same city or country that you live in should something (god for bid) happen to the item? Are they wearing the item around a group of friends that you haven't worn the outfit in front of yet?
The criteria above is what I base a lend on. I know it may sound silly to think of all these different scenarios when considering to lend an item of clothing; but if you take pride in the clothes that you buy and spend your hard earned dollars on key pieces--then you should take who you lend to seriously!