Anchie, yes, I bought two sizes of the skirt. Just one blazer. I still had planned weight loss but needed something that fit me right for an event and couldn’t wait til I lost weight. When you’re at the cusp of sizes, buying the bottoms in two sizes when you’re matching a blazer can work to expand longevity of a matching suit. The blazer is often the more expensive item but I also find it more robust than bottoms to size fluctuations.

Toban - yes, I just proved to my self in my other thread that blazers don’t show fluctuations that easily. And I am also for some reason less tolerable to pants fit. I hate with passion drooping baggy crotch

FWIW, I like the fit of your plaid pants now more than when you bought them. But yes, I have found that trousers are more sensitive to weight/size fluctuations than any other garment unless they have stretch. Fitted dresses come in second. Skirts can sit higher or lower. And even stable weight shifts around. My own weight doesn’t fluctuate much, but you have made me realize that my purchases in the past five or seven years will accommodate weight changes. Except my bras; they warn me if my weight is up. Ouch!

Not sure what I can add that hasn't already been said. I feel your pain with investing in pieces and having constant weight fluctuation. It feels like you are constantly cycling stuff in and out of your wardrobe.

I have multiple sizes because many of my nicer pieces are too small. This fall I finally bought some pieces in my bigger size and I am happier not trying to squeeze into the small pants. When I was losing weight and could not find clothes to fit I wore a lot of knit dresses. They don't have to be tailored to fit your waist, bottom and hips. My uniform was tights, knit dresses, scarves and tall boots all winter. I could just throw them on and go. It was frustrating and limiting at times but it did work. I do have a high tolerance for repeating outfits through. Then when I gained weight back the dresses stretched and fit for a while.

Lot of good advice here. Ditto about buying things more accommodating of weight changes, skirts, dresses, ponte. Especially at the smaller sizes, even a couple pounds makes a huge difference with trousers. It's also really easy, once your body is in weight loss mode, to lose too much. Never did figure out how to stop the process without rebounding...

Based on DonnaF’s comment I went back and looked at the pictures of your pant fit again and I agree with her; I like the fit now better. Obviously it’s your body and you get to pick how you want your fits, but just to keep in mind that other people aren’t going to notice small changes as much as you will.

The main thing that gets me is when an item is physically uncomfortable when my body has changed. Hidden elastic belts are one way I keep pants working through size fluctuations. I’m on mobile so I can’t add a find but I’ll try to find a link.
Womens Invisible Belt Comfortable Elastic Adjustable No Show Web Belt for Women or Men by JASGOOD,Black,US Size 0-14 Inches

I know it is difficult to show the pants fit in photos. I had to laugh that you liked pants more now, and had to do quick demonstration. They look fine in picture 1 when you don’t see where exactly they sit, except that I look long waisted with short legs I had to expose my midriff to show you the issue in pic 2. Pic 3 is where they supposed to sit. And pic 4 is with belt that I need to keep them from sliding down. But then they bunch. Maybe I am too picky, but I don’t like how they fit anymore.

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I wouldn’t give up on them. When your weight/toning stabilize, you can have them taken in at the waist so that they hang correctly. Personally, I prefer a more fluid fit through the thigh on myself, so I think these look great, other than the waist. (I’ve had the waist taken in on skirts and pants, and am always so happy with the results.)

Kathie - I was thinking of taking them in, but don’t want to do it in haste. I have to wait and see what happens, question is how long? And this pants are just example, have the same issue with all my pants. 2 more examples in pictures. I think they all can be fixed, but is it too early to do that? I don’t want to regret it.

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Don’t want to sound discouraging, but having a wardrobe of “perfectly fitting” items will always be an elusive goal. Our bodies aren’t static. Age, dietary changes, medications, exercise patterns, and fashion trends will always play havoc with fit; that’s why stylists and dressers are employed by celebrities and those in the public eye. The rest of us mere mortals usually settle for a “good enough” fit using styling tweaks, forgiving designs, and judicious pinning.

The good news is that quality garments can be tweaked by a competent tailor to adjust sizing as our bodies change. If the fit of your pants bothers you, then find a good tailor who can take them in, but do so realizing another visit to let the pants out in a year or so might be required. A perfect fit in wardrobe which holds quality items means making friends with your tailor.

Given that you’ve mentioned that your weight hasn’t been stable for longer than 6 months for quite a while, and that you have more lifestyle changes planned for 2020, I’d wait at least 6 months. Or, alter a couple things now, and the rest in 6+ months. Also, you might try moving excess fabric to the sides or back, when you wear a belt. The bunching might be less obvious.

Given the fact that you have been unwell, I would wait at least 6 weeks before making any changes. My experience has been that when a person is sick, in pain (or both), our appetite diminishes and it seems to be no problem eating less plus it doesn’t result in hunger. This is very different from trying to cut back when you are healthy - very different. Once you regain your health the body will make its way back to a comfortable and manageable weight. I have been through this numerous times at various ages and the result has always been the same. I don’t normally struggle with fluctuations, it is only after major surgery that I have this because the anesthetic generally takes away my appetite for about 6 weeks.
I can see what you mean about the pant fit but I would try and make do for just a bit longer for the reasons I stated above. Try and use welted tops and maybe some loose(r) sweaters for a couple of weeks and see how things go. I would be very frustrated too if I were you, especially after working so hard to find bottoms that suit you and that you really like.
Keep us posted!