OOTD-Vested Interest, Why Can't I Quit You?

I didn't really realize it until I was looking at my pictures, but I guess I was having what I like to call a NY uniform moment (almost, my shirt messed up the all black theme).

I have had this buffalo plaid shirt for awhile that I plucked off the sales rack for maybe $8. I'm not sure what drew me to it (I'm fairly certain it was the price), but it has a strong masculine vibe to me. I thought that it needed some love, so I decided to pair it with another wardrobe problem child, this vest. I remember seeing it on a website years ago, drooling over how special it was for months, finally ordered it when it went on sale (Merry Christmas to me!!) and now it sits in a dark closet crying over being neglected. The problem is I sometimes get lost in the armholes when I put it on and then I ponder over what the heck to wear it with. I don't know if I could ever get rid of it though because I have a fond memory of being a broke, just out of college and paying a million bills to be an adult and waiting forever for that one special piece to finally be mine.

Is there something in your closet that you just can't let go of no matter how many times you try?

Excuse the butt shot, but I wanted you to see the open back of my vest. That is all!! :)

Outfit Details:
Black/white buffalo plaid top- Old Navy (similar here)
Open back knit vest- Mason by Michelle Mason (vest with similar vibe here)
Black cropped pants- J Crew outlet
Black belt- J Crew (similar style in suede here)
Black pumps- Chloe
Black trench coat- DKNY
Black driving gloves- Forever 21