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a question I haven't had to ask since ... I may never have had to ask this question
How much difference is there between clothing sizes? When, in other words, do I know if my clothes are actually Too Big instead of just Roomier Than I'm Used To?

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Not than I can afford new pants at the moment. This has been today's experiment in unrolling the turned-up cuffs and wearing boots instead of sneakers with the boot-leg jeans. Live and learn.
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For the time when you're between 10 and 20 lbs, belts are your friends. I bought two and wore them with everything, severely notched in, until the pants/skirts were simply too rutched in at the waist, even with the belt. Then I went down a size, and it fit snugly, but not too tightly.
That's for the Queen sizes, mind you. I guess that the difference between size 6 and size 8 might not be that many pounds. But I'll probably never find out, myself, since I'd be thrilled to achieve a size 12.
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Yay on the weight loss!