One other things I just remembered - it seems like, when gaining weight, I was able to stay in the smaller size for longer before moving up. Meaning, when gaining briefly in 2010, I gained all the way back up to around 270 before I had to move from 18 jeans to 20 jeans. But on the way down, I couldn't wear 18s until I got below 250. Weird.
I guess it all depends on how you're shaped. At my heaviest at 308 I was a loose 24 and now I'm 280 and a normal 22. But I've noticed instead of wearing XXL from old navy I can wear just the XL.