I have been wearing a gen TT Yachtmaster daily on and off for 6 years. I wear it with a nice suit; I wear it with jeans and flowered shirt; I wear it with torn old shorts and a tee shirt. I climb out of my 911 or my daughter's beat up Jeep. I do the same with a Tag, Omega, Frank Mueller etc.
A guy in First Class on Continental flashes on my (gen) Omega and and shows me a rep submariner and bets me that he got a better deal than I did. Probably true.
A close friend of mine died and left his son 4 truly high end gens; everybody who sees them and even takes the time to examine them is sure that they are reps because the "kid" is only 29 and works for a living. He loves those watches and wears then daily and laughs at people when they judge him - and can't tell that they are looking at a gen.
I've had several compliments on the SFSO that I just got; no one will ever guess that it's a rep
If you're into watches, you notice and filter through your own beliefs. No one knows, no one cares if your watch is a gen or a rep. It's decoration and utility, have fun with it.
JW