Whether you’re gearing up for a big more or simply trying to un-stuff your your living space, cleaning out your closet can be difficult. There’s the shirt you wore for a special event or the jeans you keep telling yourself you’ll wear again one day…once you get them repaired. Do you even know where to find a tailor, though? We’ve pulled together a list of questions to ask yourself while you attempt to clean out a closet.

Is this a Sentimental Item?

We’re not going to tell you that you need to get rid of all your sentimental stuff by any means. Hanging on to items that make you happy can be great! However, when half your closet is filled with stuff you only like (but never wear) it might be time to trim down and reevaluate.

Was it Expensive?

You probably assign more value in your head to an article of clothing just because you know it was expensive. Guess what? That doesn’t make it fit any better or any more of a flattering color. Cost does not always equal value. Plus, you may actually be able to resell it if you try.

Have You Worn it In the Past Year?

If the item of clothing in question has made it through all 4 seasons without getting worn, there’s a good chance you won’t wear it next year either. If you’re not sure, try hanging all your clothes on backwards facing hangars and flip the hangar around when you wear it. Check back in a year to see which hangars are still backwards.

Does it Fit?

Look, some people swear by their tailors. They can make a five dollar t-shirt look like a millions bucks (or so we’ve heard). But unless you actually intend to get it altered, think long and hard about whether you need to hang onto it.

Do You Wear That Color?

There’s probably a good reason why you shy away from certain colors. Maybe it doesn’t make you happy. Maybe it brings out unflattering tones. Maybe you had a bad run in with a purple people eater as a child. If you won’t wear it, you won’t wear it.

Can You Return It?

Probably not, if it’s been sitting there a while. But if you can and you know you won’t wear it, might as well give it a go!

Is it Torn?

Again, do you have a tailor on speed dial? Unless this is an artful tear for aesthetic purposes, you probably aren’t busting this item of clothing out for most purposes. Unless you are, in which case more power to you.

Is it Stained?

Do yourself a favor and research how to actually get stains out of clothes. Get the right products (nearly all of them are pretty cheap to acquire). Do the steps that you find on the internet that others swear by. If it works, great. If not, you probably need to finally let it go now that you’ve given it your best shot.

Would Someone Else Like it More?

Got a friend who you think would look nice in it? Think your local Buy Nothing group would love to have you post it? It’s often easier to part ways with clothing when you imagine it living happily in a new home.

Why Are You Cleaning Out Your Closet?

If you know that you need to really reduce the size of your closet, you’re going to need to be aggressive about your rules. If you’re just looking to trim it down piece by piece, you don’t need to make the process all that traumatic or unpleasant.