My favorite shoe to gain a little height is a heeled loafer. I wear them frequently with jeans and trousers. The Bottega Veneta Monsieur in black and The Row soft loafer in brown are both supremely comfortable. But for something a little dressier, a pump projects a more refined style. I’m eyeing Gabriela Hearts’s sculptural GORGEOUS Sofia pump and The Row’s equally fabulous glossed low heel pump as contenders. Both are under 3″ which is my max. Jeans, trousers, dresses or skirts all work beautifully here.