SELL EVERYTHING YOU CAN.
1. Sort everything by it being worn out, tired, torn, pill-y, or faded. Toss.
No one should be (or will want to be) wearing those clothes. Even on sale for $2.
2. Now sort by what fits and what doesn’t — I’m about to toss a couple items, myself.
Things that don’t fit, are items that are baggy or too tight in areas, or just shows off areas you aren’t thrilled about because it’s highlighting a muffin top or something.
A good rule to keep in mind is if you have to keep adjusting yourself when you’re out (bra strap, hiking skirt down or up, etc), then either get a new bra that fits so you stop doing that, or toss the item.
3. Now sort by what feels good and doesn’t
Certain materials that don’t stretch or are too thin, should go. Even if it fits, but you feel uncomfortable, itchy or scratched in it, then donate it.
4. Now sort by what LOOKS good on you and what doesn’t
Things can fit but not look great, either by cut, colour or pattern. For instance, I’m an inverted triangle (straight up and down with slightly larger than normal looking shoulders), and I should ideally toss everything with skinny straps because it accentuates my broader shoulders.
I keep only the patterns and colours I like, because I can always wear them under a sweater or a jacket, but if you want to be ruthless, get rid of them.
5. Now re-assess the situation and try to fit everything into the suitcase
Look over what you have left.
I’d try to fit everything into a suitcase. If it won’t fit, you need to figure out how much more you need to pare down by — 25%, 50%, etc… and then try again with this strategy:
Do you really need 3 black wrap dresses? Not really. Pick one, get rid of the other 2.
I’m horrible at this stage.
This is where I think: But I could use 5 dresses in different cuts and sleeve lengths in cobalt blue!
But in reality, I shouldn’t keep them just because of sleeve length difference.
You can apply this logic to shoes — do you really need 4 pairs of black boots in varying heights (ankle, knee-high, mid-calf) and heels (flat, 1″, 2″, 3″ and chunky heel) styles?
Or do you need 5 black tops, with only slight variations? If they don’t really look different from each other unless you peer up close, I’d say pare down in those areas.
Or if you have too much in one area — too many tops, too many skirts… pare it down, or decide to keep your variety, but you have to cut out clothing items elsewhere to make room.
Don’t do it all in one day or even weekend
One bite at a time.
Take it one weekend at a time, and don’t get frustrated when you get sidetracked or you can’t get everything done.
.. and don’t forget to congratulate yourself after every milestone