I like these shoes from Payless. Known as the "Kimmie Mary Jane Pump," it has a 2.5" heel.
I own a similar pair in black from Payless and they are very comfortable. Maybe I should own a pair in brown ("cognac") and be very preppy!
By the way, Payless is a transgirl's friend.
They sell shoes in sizes that our dainty feet require (up to size 13, frequently in wide widths).
They sell shoes that are relatively inexpensive, which is important if you have to budget for two wardrobes.
Payless is trans-friendly. I have never been hassled in any Payless store trying on women's shoes whether I was in girl mode or boy mode.
And they are everywhere --- Payless stores seem to be in every strip mall around here.
Half the many shoes I own are Payless. I own Payless flats, mid heels, high heels, platform heels, strappy sandals, and boots and I seldom have had a complaint --- most are all-day-long comfortable.
If you have never shopped Payless, plan to do so and you will be pleasantly surprised.