Most of the time the struggle is real between what I want to keep for sentimental reasons, functionality for work, just in case social events, weight gain/weight loss because I am working on not being an emotional eater and all the other life moments happening in between.
I have many moods (which person doesn't) and I want my clothes to be reflective of these moods, so with a New year comes a New attitude and an updated/New Wardrobe.
Create a space to put your "maybe pile". This should be for items not worn in the last 3 months. This will help you organize in an insightful way, also a great walk down memory lane. For the items you like hang your hangers in one direction and the less favorable items hang in the opposite direction so you can assess what you have been wearing frequently and infrequently
If you get tired and happen to be an Epic procrastinator the pile separations will help you jump back into the task without having to start all over again. If you get side tracked just add a note to your calendar to remind you to complete this task.
It's been 6 months since you last wore it! No stress do the same thing as above, however if it has been half of the year, try on your clothes and see what it is that has caused you to not wear it...Did you lose weight? Tight around the tummy? Impulse buy...you forgot you even had a Maxi dress? Stretched out from that year you put on 30 pounds by emotional eating (truth serum), Ex boyfriend/husband bought it for you....let it go! Decide what you liked about the item originally and what you don't like about it now and determine if you want to part ways with it. If you haven't worn it for this season you probably won't wear it next season. Someone less fortunate can wear it proudly by donating it, or give it to your girlfriend that always borrows your clothes that you never get back.
Now that we have everything separated the items you don’t care for anymore donate them to your local charity,women’s shelter or to a organization that sends your items to help impoverished women and children.