ROTFLMAO
Well... I must be damned insecure (but methinks not)... I couldn't wear a Ferrari watch (or hat or T shirt), real or rep, unless I owned one... that's just how I am.
I also wouldn't wear an IWC AMG, or one of those Fortis chronos with the air squadron insignia on them... or a T shirt with 101st Airborne.. for me, it would be implying that I have, or have had, a 'strong' relationship with the outfit represented by the logo... and I don't... so I won't
If the Ferrari watch had no 'Ferrari' name or logo... I'd ear it in a minute, it's a beautiful watch... the Bentley is waaay too blingy for rough/casual ol' me though.