I think it was Allison Bornstein. Or at least I recently saw a clip of her asking this question. I find this question most useful when I ask myself do I want to wear this TOMORROW, in the current state I am in physically and emotionally.

I am not sure if it is helpful to me, because my answer can change on different days. Maybe it can help for day to day dressing, if I ask myself if I want to wear something today, but not so much for editing purposes. There are days when I absolutely don’t want to wear patterns, or days when I crave colors, or only want to wear comfortable clothes. Today, I really don’t want to wear my winter sweaters, because I am sick of them, but I will still keep them
And also if I owned and wore something for long time, excitement for wearing it is gone but I will still keep it if I have use for it.
Another question that I like to ask myself is 'Would I rather wear something else instead?'.

I do find this question helpful but most of the time I keep on asking myself if the item would work suits an oceanic climate - most of my failed items were bought thinking that I still live in a mediterranean climate. Plus, I always need to sense check if I am buying for my current or imaginary lifestyle!

I think you’re right, Jaime, about it being Alison Bornstein.

One of the spirits of the question is, I think, does this item align with who I want to be, stylewise? Am I keeping this because it fits my goals? Is this *me* or a version of *me* (depending on season, mood, occasion, much as Anchie’s comment references)? Or is it something I’m trying to shoehorn in, something that doesn’t feel true to me anymore? Is this something I can envision working into an outfit that feels good, or is it just frustrating or confounding me? Do I feel authentic in it, or like a poseur in it (for instance, in the past when I have gone too retro or too quirky or too feminine with flirty details)? When I consider that, rather than just clinging to sunk costs, my answer can clarify. Sometimes I just don’t feel like that version of myself anymore that a certain item represents. Or I’m just plain tired of an item and over it.

I can’t force myself to wear something I actively dislike anymore, just to reach a certain level of wear — when I’ve done that I do not enjoy getting dressed at all. For me, better to cut my losses and move along with tue many thing I have that I do enjoy!

Thanks for sharing this Janet. It really resonated with me. I tend to hang on to things for so many unproductive reasons. Even when I do a closet purge I keep the items just in case. If I apply this question it may be easier to let things go.

Good question! I keep things because they "work" in some way, even if I am not crazy about them. I am trying to get better about getting rid of items that feel less than fab but still end up with things that are just OK. I will be changing over to my warm weather clothes soon and need to keep this in mind.

Just got rid of a sweater answering that very question and as I changed around my warm weather and cold weather gear, I definitely eyed a second sweater that I think I also know the answer to! Like others I fear that I may get rid of too much if I ask this question, but I am thinking it might be the way to go to keep the wardrobe in joy-sparking shape.