someday clothes

I have a lot of clothes. Like, a lot a lot. Luckily, we have a huge closet so Hubby hasn't commented.

The problem is most of them don't fit me.

We got married just after I graduated college.
So, I have all my college clothes which consist of hoodies and "going out" clothes.
Married life agreed with me and I gained 15 pounds (and outgrew almost all my clothes). I was working full time, so most of these clothes are nicer.
Then, I got pregnant with The Bear. Hello, maternity clothes. I was still working full time so these maternity clothes are on the nicer end. I was in a relatively relaxed environment, so no suits or anything.
I stayed home with The Bear for a year. I lost all the pregnancy weight and then some. None of my pre-Bear clothes fit though. I was also more aware of my clothing. I'm not the type of mom to be walking around with my tummy showing (even that quarter inch that didn't phase me before felt weird).
Pregnancy #2 was when I was at home so it's sweaters and jeans.

And, here we are.

I'm 2-3 pounds more than I was when I got pregnant with The Monkey, but nothing is fitting. I also want to work myself down a bit more. Nothing drastic, just to a more comfortable place for me.

How long do I hang on to those clothes that I might someday fit into? The non-mommy friendly ones I have no problems donating. It's the jeans a few sizes too small that are hard. Am I ever going to get to someday? Or will they still be hanging in my closet in 25 years?