Over the last few years, I've curated what feels like my dream closet. I have a few special items that really feel like "me." It's been a great process of refining my style and learning when it's worth spending money on the perfect thing.

But things also change:

My size, particularly. I'm two jeans sizes bigger than when I joined YLF.

And my style changes, too, shifting along with the overall trends. Three years ago my FFBO was skinnies and a slim tunic; now I'm more likely to wear looser jeans and a structured top.

So here's the dilemma: If a truly iconic favorite item doesn't fit, or is at risk of not fitting, should I get another copy in a larger size?

In particular, my R13 crossover jeans in waxed black denim. They're amazing. They are so me. They fit, but they're getting a little tight at the waist. And someone is selling one size up on ebay for quite a good price ($50; they're $325 new). I worry that by the time I actually outgrow mine, they won't be sold anywhere. But then again, I worry that by the time I outgrow them, my fashion preferences will have shifted away!

It's not just the jeans; I'm also considering duplicating my favorite winter jacket one size up, so that it fits over bulky sweaters. TheRealReal has been a great source of items from a few years ago in different sizes. But I don't want to fossilize my fashion choices!

What would you do?