Hoarders: Clothing edition

I came across this image on Pinterest from the blog Live Simply by Annie (who looks a heck of a lot like Kate Middleton) and started to think about my closet.

I have so many things that I never wear and have definitely not worn in the past two years. Cute floral skirts from Anthropologie, seersucker cropped pants from who knows where (they are so cute!) and other random items. My issue with this is I will think about getting rid of it and then I will see a cute mom at Starbucks wearing something very similar and I think I can go recreate the look. The other issue is that most of these items would look cute with flip flops and a crisp white button down or perfect white t-shirt and how many items do you  need that only work with white? I think I need to get over it and bring it all to JT Posh and what doesn't get sold there should find its way to new owners....what do y'all think? Does anyone wear little floral skirts or cropped seersucker pants anymore? I'm usually behind the fashion curve but when I put these items on I feel REALLY outdated.

Example: I own this Anthropologie skirt, I never wear it anymore. It was adorable when I lived in Florida. I just showed this picture to M and he said to get rid of it. I said, well maybe I would put on a long sleeve shirt and go to Starbucks in this and his reply..."You don't do that". And he is right, I go in workout pants and a t-shirt. Will I change? Probably not. Do I want to be the cute mom in the grocery store/coffee shop/daycare drop off? Yes...but who really gives a shit right? Last time I wore this skirt was uptown and I had on a white twinset. I felt outdated and slightly silly.

I think part of my problem is that since I only go uptown once a week I really have no use for the casual office attire that is taking up so much space in my closet. But what if I end up in a position where I do have to dress up? There are a lot of but's in this post. I need your help!

xoxo