It's a great time to take a fresh look at your wardrobe. If you do it on a yearly or more frequent basis, then good on you. But there are many who haven't done this in years.
We keep clothes for many reasons. The best and most valid one is that you simply love a piece that has transcended time, trends and the ebb and flows fashion. Other reasons for keeping clothes include: for when we lose the weight to fit into them again, because they cost a lot and we feel guilty about moving them on, or because they remind us of a previous time in our lives and we can't let go of that.
Firstly, if they don't fit, they must go. Women perpetually chastise themselves by keeping clothes that don't fit hanging in their wardrobes, just to remind themselves somehow of their weight gain or self-perceived inadequacy. Don't. Move those items on immediately.
If you're holding on to items just because they cost a lot, you're also punishing yourself with this too. Your wardrobe should be a clear and ordered space that brings clarity to your sense of style and dressing, such items act as a barrier.
Once you've moved these items on, sort your clothes into piles based on occasions: work, weekend, dressy/going out. Then work through the piles. Items you haven't worn for 18 months are likely candidates to go. It's a tough task, but ask yourself honestly if you'd put those items on right now and walk out the door feeling good. If not, put them aside.
Also look for orphans in your piles- are there items that you can't wear because alone they don't work. If you're not planning to find your sartorial orphans some friendly matching pieces, then put them in the pile that's got to go.
Sometimes it's helpful to have a very honest and blunt friend on hand to help you through the process! While it's hard at the time, the feeling of a cleansed wardrobe is great.
The old saying that less is more certainly applies to one's wardrobe- there should be air between your coat hangers for easy browsing for a start! With less in your wardrobe it will simply be easier to dress everyday.
It also means that you're less likely to save your best for special occasions. Get your best out now and start thrashing it. So often we keep pieces we don't feel great in and wear those because we don't want to get out our favourites that are reserved for special occasions. Seize the day.
When you have a cleansed wardrobe think about how you'll rearrange it to make sense of it and so that each piece is hung well on a good hangar or folded neatly. Also treat every purchase you make thereafter as an investment- think hard about each purchase, make sure you love it and make sure it has a parent pieces in your wardrobe if it needs it.
Take pleasure in taking your pre-loved pieces to a good home (but make sure they're not shabby- no one wants your old trackies!). There are plenty of places you can take your clothes and give them a good home, including charity shops, pre-loved clothing stores and friends and family!