Let me digress for a moment to say that this is simply my opinion to generate some healthy discussion. It must be remembered that this is not an essential of the faith and, therefore, should not be treated as such.
Now, back to the issue...
So to the point: I believe wearing hats is not a Scriptural issue. I'm sure few would disagree with this position but it does need to be stated. Those who attempt to use Scripture will have a difficult time (if you don't believe me just read 1 Corinthians 11!).
By the way, do you know where the custom of taking off your hat off came from? According to the Dictionary of Phrase and Fable by E. Cobham Brewer, the custom of taking off a hat is "A relic of the ancient custom of taking off the helmet when no danger is nigh. A man takes off his hat to show that he dares stand unarmed in your presence." Obviously, there has been some pretty substantial changes in the world since that time which begs the question: when does a practically useful custom of one generation cease to be mandatory in another? In other words, how far should cultural norms that are not rooted in any way in the Scripture be pressed in a different cultural context? Is there ever a time for non-biblical customs to be questioned, discussed, and ultimately refined?
Another issue can be stated like this: If God is not the authority in dealing with cultural norms, who is? And who dictates when one stays and when one goes? Doesn't it just melt into relativity - my opinion or yours? Consider, for example, women wearing pants. There was a time when that was completely taboo - especially in church! Or what about the days of suits only? Or hymns? Did you know they were an outrage when Luther began putting his beautiful words to bar tunes of the day? Or what about praise and worship songs? They were quite the stumbling block in their early days? Basically, it seems to me that we tend to enjoy the benefits of cultural norms laid to rest while refusing to let the next generation do the same. It really is a difficult issue in which to remain consistent. Women wear pants, we all sing hymns, sing praise songs, dress "down" to church, etc. In my opinion, it seems logical and consistent that only those who deny the cultural changes of the past have a leg to stand on in going against non-biblical cultural changes today.
But does this give us the right to blatantly disregard all cultural norms of our day? Not at all! In fact, many are rooted in Scripture. Consider, for example, treating women with dignity and respect. This might be opening doors, laying your jacket on a puddle, letting her enter a door first, or any number of things. There is a timeless truth behind these that is certainly rooted in Scripture. God created women in His image. He told us to love each other and treat each other well, i.e. like mothers, fathers, brothers, and sisters, etc. Our danger is in making the action itself the law thereby nullifying its spirit.
But what if someone is "offended" by a hat, pants, or whatever? Didn't Paul say that if eating meat causes my brother to stumble then he'd stop eating meat? Yes he did. However, we must not miss Paul's heart on the matter. Paul's strategy was to not offend the "weaker brother". Notice that while Paul did (or would) refrain from meat, he also continued to teach on the subject - that eating meat offered to an idol is not wrong. He sought to reveal the true heart of God to his brother. Remember, Paul spent quite a bit of time in his letters addressing rules and regulations of the day that were no longer binding. This was very offensive to many people but he continued to do so. I believe this is because true love seeks truth. It does not endorse ignorance, nor does it contentedly smile at our brother's weakness. So the balance is clear: We avoid causing our weaker brother to stumble but at the same time attempt to help them see the difference between God's ways and culture (where they differ).
Of course, that argument could also be reversed! What if someone is truly offended by not, say, being able to wear a hat, or pants, or whatever? Does this work the other way also? Would we then have to allow him to do so? I think one would be hard pressed to find a reason why not. But regardless, Paul's point is not that we stop doing anything that offends people. That would leave each us confined to isolation rooms. The point was for us to love those who were genuinely hindered. That's very different from someone who is just judgmental. And again, part of love is in leading to truth. So Paul would stop eating meat around that brother but at the same time continue to teach his brother that God is not offended by food but, rather, by what comes out of the heart.
Bottom line: I believe, for this generation, we must not press absolutes that are not Scriptural absolutes. We will hinder spiritual seeking and development if we do. Thankfully, the Scripture is chalked full of teachings that cultivate honor, respect, dignity, modesty, and reverence. Any time we tack on our own versions of what those these look like I think we head into dangerous territory.
Ultimately, it's about love. Love on both sides. Both trying their best to serve the other. Where this happens in sincerity and truth, God is honored.
So what's your thoughts?