Tibi's Amy Smilovic Is a Viral Styling Expert—8 Assembling Tips She Swears By

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 to 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." 

By the end of it, the idea is for the reader to have every tool they need to start understanding the approach they want to take with their personal style and kickstart their unique styling journey. And whenever you need a spruce up, you can always head over to Tibi's Instagram for Style Class, a live event hosted by Smilovic and other members of her team where they discuss topics like how to get more from your clothes, as well as specific occasions and how to dress for them while still maintaining your personal style. 

Below, discover eight tricks that Smilovic says she encourages people to use when "they're getting dressed and [are] not comfortable with their look—when the vibe is off." For all other times, the goal is for you to get to know yourself and your style intimately enough that you won't necessarily need external support—you'll just know. 

"When something doesn’t feel right—not modern or effortless enough—it’s usually proportions that are the culprit. The balance of big, slim, and some skin always works for me."

"I make sure each element I’m wearing reflects my core—chill, modern, and classic. Whether it’s just a big shirt or a dress, if the piece has all those elements, I feel most myself. Our Sid Jean is a great example of this. It’s so easy, it’s absolutely modern, and it’s denim, [so it's] quite classic in that respect."

"I always make sure something that I’m wearing is giving a bit of friction—a little strange or unexpected. My personality is such that I don’t like things to be too expected. I always have a strange, little earring around, an odd sock, or an irreverent shoe that will do the trick."

"I really focus on key colors in my closet. I like knowing I can go in there blindfolded and choose any items and they’ll work together. This doesn’t mean a black and white wardrobe—it’s about really understanding a range of neutrals and how to work in more saturated colors. If that’s your thing—it is my thing."

I organize my closet by WOFs (without fails)—or pieces that are inextricably me—that I could pair with the most over the top item from Loewe’s runway and it would ground me. I would not be in costume or overly trendy—you would still see me in there and I would see me. I also love trying new things, so of course, I have an area of pieces I collect that are very modern, new, and experimental, but they have to go with my 'without fails.' If they don’t, I lose my identity [and] personal style. This is a solid way to be able to lean into style without losing yourself in the process or wasting so much because of misfires (things you buy but never wear).

"I have a small assortment of bras in a range of colors. Life is too short to worry about bra straps showing. Just own it. Color makes it more intentional."

"I don’t repeat styles in my closet. If I have a drawer of white tees, then I have an oversize one, a baby tee, a deep scoop-neck tee, [and] a plunge V-neck tee. I find that [to be] a big mistake people often make, buying the same style over and over. A range of fits allows u to really play with proportions."

"I always dress to feel like myself. There’s no such thing as clothing for 'events' and then clothing for [everything else]. Every day, every hour is your life—dress like yourself in every moment. Wear your clothes. This doesn’t mean sequins at the grocery store, [it] means observe what makes you feel best and employ that in your clothes for every facet of your life. Your sweatpants, your tees, your laying on the couch all day on a Sunday clothes, [included]."

Coming up next: 4 Ways to Wear Red Tights That Feel Surprisingly Low-Key