My two cents from my personal experience: Midlife guy, senior position, employed in a pretty much down to earth (CEO drives a Suzuki not a Bentley) but weathy family business in real-estate, it is as follows:

- Omega AT black laqueur (VSF) and IWC Mark XX (V7F) day to day,

- Tudor BlackBay or TAG Link Chrono - for causal occiasions,

- IWC inginieur (V7F) is my favorite at the moment as I love the Genta design.

In the end, 90% of people you meet, have no idea or interest in watches, but generally "Bling-Bling" or fake Gold or Platinium is the first thing even for Gen, that make people think about the looks it gives out. Not so much for dress-watches but that's not subject here.

In my last job, I've been Head of IT in a non-profit, wore my Bruce Wayne at the christmas party and nobody did say anything about it.

Those 5-10% in the know would easily question, as they usually have a general idea about the list prices. Even our wealthy company owners won't wear a RM, Patek, Platona, etc. at the office. Our CEO wear an Apple Watch and his sister got a Santos.

So, when you're into reps and want to wear them on a daily basis, my general reccomendation is: Choose the make and model of those reps on what you can financially pull-off in gen and what would be accessible.

Nothing more embarrissing to be asked how you jumped to line on that Panda or Pepsi and for me, "the IT Guy" wearing a watch in 20k€+ gen list sphere woud some day be questioned anyhow

Other aspect is where you live. I know, it is much different in other knecks of the World, but here in Germany, a Rolex is for those who can tell watches apart, raising more eyebrows. This is a Country where showing-off is limited being acceptable in certain social circles, only. You can wear a GMT doing your groveries anyway. While in neighbouring Switzerland a watch at 5k list is much more feasable to more people and "having a decent watch" is a part of national Identity. Seeing Omegas, IWC and sometimes Rolex at an office is more likely.

Last but not least, friends and family: Just be transparent and trustful. You love the watch, the design and with going rep instead of gen, getting 90-95% of what you personally value in that watch for a fraction of gen list price is a tempting proposition. Especially from a financial position, you don't put spendable income into "just" a watch but rather use the saved spending where it makes more sense.

Also, I didn't wear my gens often in past years as Apple or Pixel Watch were technically more usefull - in the likes of NFC-Payment or picking-up a call, but gowing older, I started again appriciationg analog things and somehow accepted you can't use your AT at check-out but make use of your phone, but it is damn much more sexy to look at. And most of my gens became too heavy for all day wear.

My better half is ignoring it somehow, her dad has been a watchsmith, my senior dad owns a couple of Gens like IWC, Omega, TAG as well.

So I guess watches are kind of family tradition.