However, if you are a total Carrie Bradshaw and are most comfortable in towering heels, so be it. Just be sure to know what your date has planned, since you can't wear six-inch pumps if you're going to be doing a lot of walking. If the date is a surprise, manage your heel height. Fashion blogger Billie Jean Bateson told The List, "The most important thing you should never wear on a date is extremely high heels — above three inches — if you don't know where you will go."
What if your suitor has a romantic stroll planned? Imagine how miserable you'd be in sky-high heels! Bateson continued, "No matter how amazing they look, you have to admit that they are uncomfortable and you don't want to hobble the whole time, especially if he wants to prolong the date and suggests you take a stroll down to the river. It's gonna be a nightmare, believe me!" Wearing comfy shoes means "you can be ready for anything without fear," according to Bateson.
Compromise with a manageable heel height, as recommended by stylist Jocelyn Kaye.
