So it is kind of discouraging when you think about it. I've lost around 40 pounds and am still wearing the same size clothes, as I did at my highest weight. Then I got to thinking about, I like my clothes loose. But when do I know when it's time to shop at a lower size? Shirts kinda stay on you, even 3 sizes too big. But jeans? When you put them on and they fall to your knees? I've only ever gone up in sizes ("oh these don't fit, let's try the next size up." That's easy). When do you know to try shopping for a smaller size?

Whenever you want!

There is no rules, just how you feel about things.

Dropping the first dress size can take the longest and as you said, loose clothes still feel alright. The same amount of loss in future will see bigger changes happening.

However there is a degree of 'coming out' associated with new clothes. We stay hidden in our old clothes and people are less likely to notice our weight loss. Wear new clothes, especially if there is a style change brings things to their attention.

It is always good to have at least one outfit that fits our current body at all times of then journey, so we can see and feel good about what we have achieved. When to go buy it is when you are ready to.

Knock yourself out!

Ugh I have this same problem!!!

I've lost 30 and things fit better in the sense that they're looser, some of my tighter stuff looks better, but I can't fit into anything a size below, maybe it's because I'm short? I've been told 50 lbs is when you get to see a big difference, but man these last 10 lbs were so hard, I wish I would get a little motivation through clothes!

I just went shopping the other day, and it felt awful. I truly hate shopping for clothes. Nothing fits they way I think it should and I always feel like I'm resorting to buying stuff "because it fits" rather than because I like it.
ok rant over. Sorry! But I totally feel you! Maybe 50lbs is the magical number?!!

I feel you on this one cos I've been wearing size 12 my whole life!
Let me explain: fat or thin I've always had curves: breasts,legs and butts. This might be your problems too?
Those basically don't vary. When I put on a lot, I fit in 12-14 size clothes, but then when I lose too, I never get to size 10 cos some curves of mine will never fit in anything 10! It's always too tight at those places: breast, legs and butts. So you'll know if you have the same problem if the rest of your body fits perfectly in a smaller size but some particular areas refuse to go into anything smaller. That's just my opinion.
So in my weight loss journey I'm not looking at size changes. I know I'm condemned to wear size 12 for ever and no matter what. What I'm currently looking for is just to get rid of the 14 for good.
Your weight loss has been tremendous though! So keep it up and don't let this be a setback.

This! I've been stuck in a 14 for ages! I am ALMOST in a 12 but not quite there.

To the OP, I noticed when I started my journey I stayed in the same size for the first 30-40 lbs. I actually had a favorite pair of jeans I stuck with through that period and what I noticed is I continued to wear them and as frustrating as that was not to go down a size I noticed they looked better on me...I had never noticed at my higher weight that they didn't set properly on my waist (darn big belly! LOL!) and were a bit awkward looking on me ...because they pulled up in the waist they hit me at an odd point at my ankles...I could probably dig up some old photos I stuck with them until I noticed one day I pulled them out of the dryer and they fit fine, but as the day progressed they kept stretching out and I had to keep pulling them up. I also noticed they were floating around my legs! What a great feeling!
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There are at least three factors at play here:

1. As Electro mentioned, there is a degree of getting comfortable with the changes to your body that takes time. I am comfortable wearing much more form-fitting clothes now than I was when I was fatter, and that took time to get used to. So there was a time when I would try on some size and think "that fits." But if I were comfortable with something more form-fitting, I would have tried on the next size down and found that it fit too - just, differently.

2. Often there is more difference between larger sizes than smaller ones. So, the difference between a 20w and 18w can bigger than the corresponding difference between a 14 and a 12.

3. A phenomenon often described as "paper towel theory" - the idea is that 10 pounds off your body when you are at a high weight makes less of a difference to your three-dimensional size than 10 pounds off your body when you are a low weight, like a paper towel coming off a full roll versus an empty one. Search 3FC for "paper towel theory" to find very good explanations of it. That combined with #2 means that you might have to lose a lot more weight to drop your first size, but later size changes will come quicker.

I have no real answers for you. I HATE having clothes 'touching' me, which means that i always prefer clothes that are a little big on me. If they actually fit, I feel like i'm choking!

OTOH, on some levels i recognize that baggy = doesn't fit [see? i have this whole body perception issue going on].

So, some observations. If i can pull a pair of non-stretch pants on and off without unzipping them, chances are they're too big [or almost too big]. Doesn't mean I'll replace them, but i WILL acknowledge that they're getting too big.

Stretch pants, yoga pants, knit pants? I'm HOPELESS here. right this second, I'm wearing a pair that I KNOW are at least two sizes too big. I KNOW my legs look like elephant legs in them. But I'm still wearing them!

And SHIRTS!!!! if i can fit another fairly thick shirt under them, they're too big. if they're falling off my shoulder, they're too big. doesn't mean i'll stop wearing them, but at least there's a chance that I'll acknowledge that they're too big.

I also have a couple of pairs of jeans that keep falling down. I kept wearing them until someone got fed up and bought me A BELT!!!!

really, I'm pretty pathetic when it comes to clothes. But I hope that maybe I've given you some ideas about WHEN to get some new duds. Just because I don't pay attention to those signals - well, that's my issue, and i'm working on it. sort of.

Carter, I am glad you mentioned the paper towel theory. I use it a lot because I noticed the effect quite strongly during my own weight loss.

To OP, I thought I would add that I would tend to go shopping whenever I found myself twitching and hitching my clothes too much during the day.

I did delay getting new jeans so long that at one stage I accidentally mooned other shoppers when I was reaching down to pick up my grocery bags. Now that was s clear signal to at least buy longer tshirts (I find jeans and work pants hard to find, even now)

I just know it's going to take almost 30 lbs. for me to go from a size 18 jeans to a 16, and God I hope I'm wrong. But I doubt it. Since I'm bottom heavy I've never had the problem of pants feeling like they're going to fall off. Though shirts will get to large around the shoulders which is quite easy to tell so I know when to shop for smaller shirts. As far as my bra size, being that my goal is just losing one size, I will still stay a 42C....ugh. I just don't lose weight in my breast for some odd reason. I wouldn't mind being a B.

This sounds a lot like me. I kid you not I lost almost 40lbs and I changed ONE SIZE. How is that POSSIBLE? I'm still stumped.

I think it varies. When I was 225 I wore a size 18. When I was 180 I still wore an 18. It wasn't until I dropped to 175 than I magically got to size 16. I've got beefy thighs and a large bum, so that probably is why.

FWIW, in my current weight range, ten pounds or so seems to be a one size difference for me.

Yes the smaller the size the fewer pounds between them, partly related to the fact that smaller clothes get more fitted and the smaller you are the tighter you are comfortable wearing them.

Sounds like you're shaped just like me. I wear an 18 also as I did 10 lbs. heavier and when I try to put on size 16 pants I can tell it's going to take a lot of lbs. to get down there. Hopefully 30 lbs. but I think that's wishful thinking.

My driving force was when I could absolutely not keep my pants up any more...belts do nothing for me because I have no butt or hips, so i just had to go down a size when they got loose. I went from a size 12 jeans to a 4 going from the high 190s to about 150. My 4s are loose now, but I don't want to go lower because my pants still *MOSTLY* stay up and I don't want my thunder thighs to look like sausage casings.

Gravity made the pants size easy to determine, but almost 2 years after losing the bulk of my weight I still have no idea what top/dress size I am. I still have things that still fit in a vaguely tent-like way from my high weight just because I can't be bothered to find things in whatever my proper size is to replace them. When I buy new clothes I just end up holding them up in front of me then bringing the 3 sizes that look closest with me into the dressing room. Honestly there's enough variance between brands that it's probably not entirely possible for me to determine a size overall since my top and bottom are so out of proportion with each other.