I do keep clothes larger & smaller even if unworn, that I love because my weight shifts a lot with medications and hormonal issues but anything of any size that I don’t love or still want to be able to wear, goes.

A few years ago I let two too small beloved skirts go, then got to that size and deeply regretted it.

Last year I donated stuff that was too big and now, have gained and could use them.

For me, it’s definitely tricky size wise.
Otherwise, I don’t have a problem culling based on other parameters.

I echo the advice of others to let these items go. I like Carla's litmus test. You look SO amazing in that navy dress. All occasion wear should be up to that standard. Keep only things that make you feel great.

Having said that, I can empathize. I kept a number of items in my closet for longer than I probably should have and only got rid of them recently.

Having just lost significant weight (35 pounds) right before I joined YLF, I was at my lowest adult weight when I made my first YLF-related purchases. I maintained the new weight for about four years but then high stress levels got in my way and I regained about 10 pounds -- returning to what had been my former (pre-weight gain) set point. Then, this past summer, I lost about 5 of those new pounds. So much like LisaP, I now find myself betwixt and between.

If I'm honest with myself, this is my more comfortable and sustainable size. I know that even if I stay this weight, I might lose some extra cms. once I'm weight training again more regularly, and that will affect how things fit. But the truth is, I will want new things at that point anyway.

I do think ill fitting items taunt us and make us feel guilty if they're hanging there. Letting them go can be liberating. You don't have to live with guilt.

So much wisdom here that I needed to read as a reminder! Thanks, all. I’m on my phone in the airport, so not possible to address all of your smart responses individually, but I’m glad to get all of this encouragement.

I have lots of fab things that DO fit me, and my life seems to get more causal each year. I don’t need to hang onto so many “nice” items when they would fit someone else’s life and body better than they fit mine. Clearly a good edit is in my future!

I am right there with you, girlfriend. I've gained more than one size in the last 18 months.

Some of the most "precious" or exquisite items are in my holding zone, just in case. Overall, though, I've come to realize that my tastes are likely to change by the time I can fit in them again, so it makes it easier for me to pass them on to someone who will love them.

Sending you (((hugs))) because I feel your pain

I commiserate and also am in the same situation, having gained 2 sizes in the last couople of years and now back down a bit but still up from where I started. I do keep non-fitting things out of my closet, but don't get rid of the special (designer or vintage or both) ones but keep them separated to be checked if I lose a size. A relatively small weight change makes a huge difference on my short and small frame, and I also have two mini-mes who have begun to raid my stuff, and appreciate it. But things that are easily upgradeable and replaceable are definitely sold or given away.

I am keeping a few pairs of pants that are a size down from my current size, because pants are SO hard for me to fit (especially now that rises are trending higher). A couple of items that were gifts from my husband. And a couple more with really distinctive/beloved prints that I know I would want to wear again. Fewer than 10 items overall. I try to keep the number of such items pretty minimal, because let's face it, clothing actually doesn't store all that well.

I like the idea of using your blue dress from this summer's wedding as a benchmark for your occasion wear -- it was sooooo stunning on you!

Oh Janet. You look so amazing! It is a pity to do this. I do it too, and in a more extreme way. It isn't the dress from 1993, it is the two dresses from 1984! One is a perfect simple cream silk that I secretly hoped older DD would wear, but she hasn't. And one is my first really "grown up" dress in red and black, bought for me by Mum for my cousin's 21st and worn to graduate as a doctor the next year, 33 years ago. Realistically for me I'll be an old lady of 80-something who has lost weight through illness and frailty before I will fit these things.
I see so many post-menopausal women who have gained weight, it's just so common and actually helps our bones somewhat since fat cells make some estrogen. A bit to come and go on is good after 70. Illness can play havoc with weight and lead to frailty. You haven't failed!
This year I have donated a skirt from 1997 and one from 2000 that were in my holding zone. They were special too but not as much as those 80s dresses. I am trying to be emotionally strong and to not hate my body. It takes work. I mostly succeed. To look down at clothes that fit me now, fatter body and all, makes me feel happier than self-flagellation x

LisaP, I’m no good with links on my phone, but on 5/25 you posted a picture of a black with white stripes cold shoulder dress that I loved!! One of my favs.....

Janet -so much good advice here. I know it can be hard to follow -I too keep things that taunt me. I hope she my busy travel schedule allows that I can re read and embrace this wisdom. Sending hugs and affirmation that you do indeed look FAB right now.

@JenniNZ - I don't think many of us can fit into the clothing we wore in 1984 again, I know I certainly cannot. It does not hurt to hold onto items that mean so much to us and those two dresses sound like they are special. I still hold onto my wedding dress, despite only having a son and having absolutely no intention of ever getting married again (and if unfortunately that occurred, then that would be my ultimate excuse to splurge on an amazing new dress). You make a very good point about ageing. Yes I would love to have the looks and figure I had in my teens and early 20's, but I just have to make the most of what I have now and value my health and happiness. Thanks for your wonderfully wise words.