My K/R process:
Am I thrilled by this item, at our first meeting? I know that the first time I put on a new item, that's the biggest 'thrill' moment I will ever have for it. I've never become more excited about a wardrobe item that I was 'eh' about at the beginning. The exciting shiny new feeling wears off over time, but if I've shopped for the authentic me, I will still have a deep love for the item until the day I wear it out.
But if the thrill isn't there from the outset, the love doesn't last.
I look at aaaaall the other clothes in my wardrobe: the pieces I love to wear and can't wait to put on, and all the other stuff that I continually shift around to get to the pieces that I love to wear and can't wait to put on. Which one is this? I usually know immediately.
Sometimes I get an item I'm super-excited about, but can't quite make work. For example, I recently thrifted a really cute BCBG swingy skirt that I get excited about just looking at. But I couldn't seem to make it work. So I tried it on with every top in my closet, until I honed in on the look I wanted. I made some outfit notes, and this skirt is ready for summer outings. I'm good with having to shift it around on the rail to get to something else, because I have a solid vision now for this skirt, and expect to wear it a lot over the summer months.
One more K/R thing is that sometimes I have to concede that despite that gorgeous color, or that wonderful style, it just isn't working for real-life, three-dimensional me. And that's okay. I recently thrifted a glorioius winter white Ann Taylor knit skirt, that ticked all the boxes, except for the most important one: I couldn't make it work in any outfit attempt. It was too big, and no amount of tucking, belting, hiking up higher on the waist, etc. could make it look right. It can't be altered, because it is one continuous knit. So I'm passing it along to my sister (who is thrilled, btw). But now I know that if I see this skirt in a smaller size on a resale site, and it's in great condition, I will pounce.