Closet Questions!

I decided to start an early "spring cleaning" of my closet.  I have high hopes for a new wardrobe this spring/summer as my body changes so I felt a closet purge was much needed. During my purge I discovered my closet says a lot about me and it even raised a few questions!
First:  I have the HARDEST time getting rid of clothes!  Even things I haven't worn in YEARS... Yes, YEARS!  It's especially frustrating because feel that a lot of my wardrobe is made up of "2006-2010 Kyla" clothes and I was at SUCH a different space in my life.  Why can't I get rid of these clothes? I need 2014 Kyla clothes. What do I do?
Second:  How long do you keep Christmas PJ's? I seem to have 5+ years of that favorite Christmas Eve tradition stacked up in my closet.

Third:  Is it true gauchos are really out of style? I STILL Love mine. They are so comfortable and perfect for a comfy casual day in or quick trip to the store!  (Yes, I still wear them in public)

Fourth:  My closet totally shows that I'm a California Girl. Disney shirts and SwimSuits for Days! 

Finally: I LOVE Shoes. Like, Obsessed, buy as many as often as possible obsessed. I have some pretty adorable shoes that don't get worn as often as they should. What's your secret to switching up your footwear?!

Three bags of clothes now sit on the closet floor. Winter, Maternity & Donate. Just missing one.. New Clothes!