In New York, fall starts now. Shorter days, playoff baseball and a reasonable chance to wear tweed. It’s an ideal time to reset your wardrobe, a good habit which puts you on the wise path to owning fewer, better things. Clearing out the sartorial dead wood can be a point of pride: As your taste evolves and you move up in the world you might invest in better suits. All of a sudden the previous iteration doesn't look so hot. There’s no shame in that, just get rid of the old guard.
So make a giveaway plan. Is there a young person in your life who just got a corporate job and needs ties? Great, give him some of the old Repps you don’t wear anymore. There are plenty of places (Housing Works is one) that are happy to take donations in good condition. Having a good donation destination will clarify your thinking.
Take a weekend day and engage in a clear-eyed reassessment. I do this myself and you should too. Haul everything out of the wardrobe and drawers (or most of it anyway). Air it out, take a look at it, try it on. You might find some old friends in the back of the closet. A few might have mysteriously gotten smaller in their absence. But when you put everything back make sure you’ve got the right edit.
Here a few ideas to help the process.