Journey to Fashion-less Design

At what point do we change from caring about how we look to others to just wanting to be comfortable?  I went shopping the other day and saw something really cute hanging on the wall and began to walk over to it, but then I realized it was in the "teen" section and I'd look ridiculous in it.

So I walked over to the "Old Lady" section....just like my mother!

I buy things online now so I don't have to try them on at the store.... just like my mother!

I shop for things that hide my arms, hide my legs, aren't trendy, are more comfortable than fashionable....just like my mother!

Now I wear clothes like my mother. And I embarrass my daughter.  I've come full circle.