frilly: details on your dub monks, plz?
On the shirt cuff question, most of my watches fit comfortably under my sleeves....particularly the ones that I wear to the office.
But if it's bad combination of too big a watch/ too snug cuffs, then I just push the sleeve back slightly and let the "edge" of the shirt sleeve ride under the watch case. It kind of forces the watch lower on the wrist, basically. I maybe have only a couple of timepieces (or tighter-cuffed shirts) in rotation where this is necessary.
That approach however, is NOT to be a d-bag or show off my watch to anyone else....strictly so I can see it and enjoy it. Oh, and uh..tell the time at a glance.
I can also see the sprezzy approach of leaving a button undone if necessary, but I guess that's not my way of resolving it.