There are days for dressing up and there are days for just plain comfort. I remember discovering Lou and Grey a few years back and thinking that I had found the hidden gem of clothes. Everything I’ve purchased from them feels like you’re wearing pajamas, except it’s actually something you can wear out.

I’ve been trying to keep myself accountable for dressing up more since the weather in New York has been all over the place. Last week we had a few of the hottest days of the summer followed by 4 days of rain this week. I know myself well enough to know that this time of year I tend to gravitate back to the easiest thing I can find in my closet. The mornings get a little darker going into fall and I find myself sleeping in.

I decided to try something new for cleaning out my closet this year as fall arrives. Instead of going through and unilaterally deciding to choose things to get rid of, I’m trying to create as many outfits as possible as summer ends and the real transition happens (and attempting to document them on IG stories under “Everyday“).

I’m then going to go back through all of my summer clothes and pull out anything I didn’t wear a single time this summer – it’s going to be a little alarming I’m sure (especially because historically I shop the most during the summer) in one pile and then categorize everything I only wore once in another pile, while grouping everything I wore most often in another pile.

The goal is for me to visually see all of the stuff that I no longer wear (and get rid of some things) and to see the things I’ve been gravitating to the most to help build next year’s summer wardrobe around those pieces. I’m a highly visual person and also a creature of habit, so for me it’s helpful to see it all laid out and know what I need to stop buying.

How do you clean out your closet?

GET THE LOOK

Lou and Grey dress | MULES (OLD SIMILAR HERE) |  SUNGLASSES | BAG (SIMILAR)

Photos by Carter Fish