The easiest way would be online. There are sites that are deliver with plain boxes and a lot more options/styles.
Measuring size is the same as figuring out clothing. Just measure your hips/waist and find the size that matches.
In person can be a bit more embarrassing, but you can use cash no one's going to really stare/shame you or ask about it. If anything you could make an excuse like you're buying for a family member or are donating them to X.
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 5' 11" Straight Male.
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