Think about context

When deciding on the font, it's important to consider the context in which the font will be used. Where will it appear? What message will it communicate? What kind of impression does it need to produce? Look for fonts that will match your design goals in terms of readability and appropriateness.

Let's take as an example a heading for a financial advisor service website. It needs to be elegant and legible — but not necessarily as legible as the body copy. It also needs to produce the impression of trust, reliability, and professionalism. The client suggests either Playfair Display or Lobster.

While both typefaces are stylish and highly legible, their aesthetics are quite different. Playfair Display is a classical typeface with a modern feeling that takes inspiration from the 18th century. Lobster, while a sleek and aesthetically appealing font, has a more playful personality. Moreover, it became the victim of its own success and has been heavily overused. In this case, Playfair Display is a much better fit for the job.