IMO, this needs a little nuance. First, where do you live? Farther
south, where even the annual herbs will grow late into the year, they
can flower, be cut, flower again and again be cut.

I don't know where the original poster lives, but if you cut them once a week
at less than half the height, they aren't going to flower - anywhere. Unless
you have some super-duper speedy growing Audrey (little shop od horrors)
version of an herb. If that is the case, you have far more important problems
than flowers to worry about....[g]

Second, which herb?

The original poster was asking about oregano. Says so right up ^ there.
-=epm=-

In matters of truth and justice,
there is no difference between large and small problems,
for issues concerning the treatment of people are all the same.
- Albert Einstein