I had such an opportunity, but the shoes didn't fit very well, sadly.
While the flared leg has some potential, the absence of any toe showing is a give-away. In fact to be truly discreet, a high heeled shoe worn by a man must be 2-3 inches longer than usual. I have some very wearable shoes (easy to wear) I could walk around in all day. Slightly flared (bootleg) jeans or trousers, hide whatever needed hiding of the heel, bit no toe showing, draws attention. Less, is not more in this instance. I have some very nice ankle points with pointed toe, that fit very well. They are half-way toward a cowboy boot, but the absence of my foot showing, suggests I am wearing a heel, and draws attention for that reason. The appearance at floor level, is of a girl wearing high heels and just a bit of her toe showing at the bottom of her trousers. Even people not into heels, recognise that look.