One of my watches has a chain and T-bar. I tend usually to wear it inside.
Hmmm. Should we start calling that "dressing inside" versus "dressing outside?" 
One of my watches has a braided leather strap which can be fixed to the vest with one of the vest buttons. Typically buttoned on first, then the vest buttoned over it.
One of my watches has a leather thong with a loop in the end, intended to be looped through a belt loop and worn with p*nts which have a watch pocket.
One of my watches has a belt hook on the chain and is worn with p*nts which have a watch pocket. When I wear it with a kilt I hook it on the belt and simply drop the watch into the lovely kilt pockets Steve puts in.
Three of my watches have no chains. They were inherited from my grandfathers.
I have noticed that many men used to wear fobs of one sort or another: Masonic, fraternal (such as the Organization of Railroad Telegraphers), military, religious or otherwise personally symbolic. If those were on the end of the chain one would want to display them and so would "dress outside." (Unless one wanted to be somewhat clandestine, I suppose...) I've seen more fobs on the end of the chain than in the middle somewhere.
Most interesting fob I ever saw: Met a guy who lost half a middle finger in a shop accident. Lopped that sucker off nice and clean. Packed it in salt and carefully dried it out, then varnished it and made a fob out of it. He'd hand it to anyone he thought might need to be "given the finger." I'll admit it takes a certain robust sense of humour to contemplate that.
Dr. Charles A. Hays
The Kilted Perfesser
Laird in Residence, Blathering-at-the-Lectern
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