I don't think anyone has mentioned Federation Commissioner
Nancy Hedford from 'Metamorphosis.'
There have been lots of great suggestions in this thread already. personally, I'd have like to have seen Yvonne DeCarlo as a no-nonsense Commodore or Admiral.
Yvonne DeCarla would have been great! So would Barbara Bain - she would have made a great captain or at least a commander - and Anne Bancroft would have been just fab.
Others from the era that come to mind: Faye Dunnaway, Vanessa Redgrave, Glenda Jackson and Blythe Danner. Can anybody think of any women of color? I did a quick google search and...golly, there weren't that many working in Hollywood, aside from really big, out-of-reach stars like Lena Horne (Dorothy Dandridge died in 1965). Man, that's just not right...no wonder so much attention was paid to Nichelle Nichols and Dianne Carroll! I knew it was bad in those days, but I really had no idea how bad.
And actually, it would be nice to have some women who aren't young, either - admirals aren't usually still in their dewy youth. I'll see who I can think of.
I've always felt that the best way to interpret Lester's references is from the perspective she was an embittered loon. Starfleet evidently couldn't miss that she was psychologically ill-equiped for the command track and kept her from it. She wouldn't be the first to perceive this as sexism rather than accepting her own shortcomings.
I simply accept that there are indeed female command officers in the TOS era and that we regrettably just never got to see them.
That's pretty much how I choose to see it, too. I accept that it was a purposefully blunt metaphor for dealing with sexism in general, but I choose to reinterpret whatever obvious 60s sexism is present in order to make the it more plausible.
This is pretty much what I do, too. I just choose to interpret/pretend that (1) Janice is a loon, which she undoubtedly is; (2) that her comment is directed at Kirk out of her looniness; and (3) that there are female officers of all ranks, but that after
The Menagerie, it just so happens that we don't see any in the highest ranks. Mind you, I am not by any means sure that's how TPTB originally intended that episode to be interpreted, but I let myself think of it that way - this allows me to enjoy what is otherwise, I think, a very interesting episode, and also to not think of my beloved TOS Starfleet as a good ol' boy network.
I've also wondered if the ambiguity was there on purpose? That TPTB, just to avoid trouble (with the network or whoever), wanted everybody to be able to interpret it in the way that they prefer? Could be...