Vionic Brandi Ankle Boot — Black Leather

The most support-forward ankle boot under $250. Vionic’s built-in orthotic footbed is the key spec here: a clearer support signal than a generic foam insert. Round-toe leather upper looks appropriate in a conference room without trying to be a dress boot. The cushioned rubber sole is why it leads this list for long city days; confirm fit and arch feel with the current retailer reviews.