She's most likely to wear this outfit combo to a Friendsgiving or family holiday dinner, so the styling pieces need to read party-ready without being overly formal. "Use accessories to elevate the look," she says. With this in mind, Naylor chooses comfortable block heels and a faux-leather jacket (think party on the bottom, business on the top). "I love finding supple faux-leather options that really make an impact," she says of this stylish jacket, which by the way, looks at least four times its price IRL.