NOTE: This is not complicated, it just requires a plan and a willingness to stick to the five steps.
You'll need to 'shock your mindset' about your current wardrobe.
Set aside a weekend morning. We highly recommend this be done quickly and all at once.
Lay out everything on the floor so you can see it. Organize piles into categories: sport coats & suits, trousers, dress shirts, sweaters, etc. You get the idea. (Note: The piles will probably shock you, since you are now seeing your entire collection of dress clothes at-a-glance. You'll now be able to visually quantify how much you own and how many things never get worn.)
Now assess each pile and identify things that spark a good feeling. Pull those aside. This step is about identifying things to potentially keep, NOT things to discard.
Now make three new piles: What to keep, what to donate/give-away, what to throw away/recycle. (Note: Grab a box or bag for any items that can’t decide you want to part with just yet. Date the bag/box, store it aside, and assess again in six months.)
BE RUTHLESS! Simply purge any/all items you have not worn in a LONG time. This will feel liberating. Plus, you could make a friends day, or a thrift store and customer very happy with something you no longer want or wear.
Once you have made the 'cut', what is left is what you are going to keep, BUT first try everything on. If it doesn’t fit or it doesn’t make you feel good; get rid of it. (Note: Some things may just need tailoring. Bag those separate for a visit to your tailor. FYI- we provide tailoring for both men’s and women’s clothing.)
Take five and breathe a sigh of relief. When your done you will be very surprised at how little is left (This is ALMOST ALWAYS the case). Now start looking for 'holes' in your wardrobe, then start a shopping list of what you'll need to properly complete your new FIT KIT simplified wardrobe.