MB, I love the SOGOTP idea! One caveat I’d throw in though is the question I originally asked in my post—when, in the various trends that have come and gone while you’ve held an item, could you have worn it?
Think, for example, of anyone who loved flared jeans 1 or 2 decades ago. I’ve pulled my black Gap baby boot cuts back out and am perfectly happy to wear them now, but for years I couldn’t wear them simply because the world belonged to skinnies. Same might be true for olive. It isn’t a color I wear, but it sure seems like people who adore it and look good in it are jumping up and down now because it’s suddenly become an acceptable color to be seen in, in a way that wasn’t true for a long while. Nothing against olive or bootcuts, but even if an item was perfect for you and your circumstances, you still might want to tuck it away for a few years.
