Having been sent through that experience a few times myself, a few things I've noticed.
That's a reasonable start in finding your size, but it's always best to try things on if you can, especially jeans. jeans you have little reason not to, as there's almost no way to tell at a casual glance whether you're carrying men's jeans or women's.
For checkout, use any method you like, so long as you keep yourself from looking totally embarrassed by what you're buying. If you're squirming all around and blushing, they'll figure you out. If you just go up to the counter as if it were the most natural thing in the world, they'll check you out and then forget you. You could be buying presents for someone, creating a gag gift for a guy fried, buying random things for a ToD party (xD) or any number of things. Most times they wont ask. (Though sometimes they've commented to me about how cute my selections are. Apparently I have good taste =P)
Last note, if you're buying new clothes at the self-check, at most stores you're going to have to deal with a clerk anyway so they can take off the security tags. May as well save the time and have them handle it up front xP
Hope this helps a bit.
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