What is smallest fastening size?

The belt has fastening holes the entire length of the belt. So to answer your question, you can make it as small as you like.

What is the correct side to wear?

The rubber prongs should face outward.

Do you have to wear slightly larger pants around the waist due to the added thickness of this tailor belt?

No, it should actually sit right below the waist line of your pants to hold your shirt down, also I wouldn't recommend this specific one, it broke/tore twice in a few weeks whereas the first one I had, a white-ish yellow colored one, lasted 6 months, I would suggest looking at the shirt stays plus super belt, it's the best one I've used yet

Can i purchase the button alone? I lost mine

I lost mine one time and replaced it with a similar button that screwed in that I purchased at a fabric store.

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Hero's PrideHero's Pride Shirt Tailor Rubber Belt - Adjustable Shirt Stays for Men - Non-Slip Shirt Keepers For Law Enforcement

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