I notice that some of the more stylish people I've met find one or two items that they wear the hell out of for a season, a year, or two years. This might be a moto jacket or a certain scarf. The important thing is that they do not care if they repeat it, even up to daily, if they want to.

Myself, I tend to have a handful of items, but wear them all approximately equally, if I can. Goes for jewelry, shoes, clothes, etc.

I suppose one way of looking at this is, do you have a "signature" item that you wear all the time? Or if you don't consider it signature, do you at least do this pattern of wearing the hell out of a single item for a time, on purpose?

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