Doling out styling tips is tricky. After all, style is inherently personal, so if you want to consistently get that effortlessly cool look, you’re probably not going to get it by copying tricks from the internet. That’s why I always go to Amy Smilovic’s Instagram when I need inspiration—she gets it. “Thinking in terms of outfits is like trying to learn a language by just memorizing words to string together random sentences,” she tells me. “It’s when you really understand the language, the grammar, [and] the structure that you begin to communicate, effortlessly and with confidence.” 

As the creative director of Tibi, the New York-based luxury brand she founded in 1997, Smilovic has mastered the difficult art of giving styling direction while simultaneously sharing with anyone who’ll listen her tips for understanding your own personal style and dressing accordingly. She’s such an expert in the field, in fact, that she just wrote a book about it, titled The Creative Pragmatist. Specifically, the book focuses on a sartorial philosophy that she calls “creative pragmatism,” which is meant for the dresser who “craves the emotion that style can elicit with functionality and utility,” Smilovic explains. She wrote The Creative Pragmatist after her DMs were flooded with messages about all things personal style: “The book was my way to put all my thoughts in one place—an encyclopedia of sorts for those who like to take an analytical—in addition to the visceral and emotional—approach to style.” 

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