I don't currently own a suit that doesn't make me look like a time traveling clown. I need one, but not for work, just for general wedding and fundraiser dinner type purposes.

I think I'm in that awkward window of time where everything I own is hopelessly out of fashion, but I'm not yet old enough to not be aware of it. So I either need some new clothes, or just hold out about 5 more years until I'm sufficiently out of it not to even know.