To keep or not to keep?

Teal dress outfit with denim vest and espadrilles — Cotton Cashmere Cat Hair
Soludos leather espadrilles outfit with teal dress and denim vest — Cotton Cashmere Cat Hair
Denim vest summer outfit with teal dress and tan espadrilles — Cotton Cashmere Cat Hair
Madewell pocket denim vest outfit with textured dress — Cotton Cashmere Cat Hair
Denim vest, textured dress, tan Soludos espadrilles — Cotton Cashmere Cat Hair

I've decided to make it a point to style some of the items I've had for a while but haven't worn much and can't seem to part with just yet. This dress is one of those items. I can't even remember when I got it, but I do know it has only been worn a handful of times (last featured here February 2015). I used to be a die-hard fan of fit-and-flare dresses. They were pretty much all I wore for while, but now I'm not as enamored with them. They feel too sweet and less like "me" nowadays. I put this on yesterday, but even with the vest and espadrilles, it still didn't feel quite right... My boyfriend, on the other hand, really likes it because it's different from the rest of my closet.

I'm trying to decide if it's worth it to hold onto these items that I still love in theory but don't love as much on me and don't really fit into what I consider to be my personal style. I also might be transitioning into more of a "professional" wardrobe in the future and thus won't be wearing my casual clothes as much (which is basically my entire closet right now). What are your thoughts on keeping items like this?


Madewell vest / exact (last seen here)
Target dress / old; shop all Target dresses (last seen here)
Soludos espadrilles / exact (limited sizes) or similar (last seen here)
Dior Addict Lip Glow in pink / exact