Life-Changing Advice from 50 of the Most Interesting People We Know

Esquire / Getty Images

We’ve doled out our fair share of advice in the Big Black Book, but we don’t presume to know everything. So we reached out to 50 of the most interesting people we know—performers, designers, editors, CEOs, photographers, jet-setters, and more—to ask them for one piece of advice they’d like to share with the world. Here are their collected words of wisdom, the inaugural edition of a project we’re calling the Knowledge. From expert travel tips to new philosophies on personal style, consider this your guide to a life well lived.

london, england january 06: tim little, grenson creative director, attends the launch of the new balance x grenson phase two collaboration launch during london fashion week mens january 2018 at 37 jermyn street on january 6, 2018 in london, england. (photo by david m. benett/dave benett/getty images)

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“Never wear socks that are funnier than you.”

— Tim Little, CEO of Grenson

Daniel Prakopcyk

“Style is all about finding your own lane—something that feels like you and nobody else. I’ve always been drawn to style that you can’t quite put in a box. I also love mixing and matching. High fashion with something inexpensive, or new with vintage. Whatever you do, just be creative with it. Let your style speak for you before you even say a word.”

— Shaboozey, rapper, singer-songwriter

milan, italy february 25: rosario toscano attends the londonshowrooms evening event by british fashion council at armani hotel on february 25, 2022 in milan, italy. (photo by victor boyko/getty images for bfc)

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“When shopping in Japan, always carry your passport with you to unlock tax-free savings of 10 percent. And be sure to pin the Uniqlo mega store in Ginza on your Google Maps; it’s a nonnegotiable stop.”

— Rosario Toscano, CEO of Akoni

new york, new york september 03: dapper dan attends the 17th annual harlems fashion row fashion show style awards on september 03, 2024 in new york city. (photo by johnny nunez/wireimage)

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“In order to see innovation within the fashion industry, we have to be present internally to make change. Get involved and try to generate as much exciting energy as possible so we can push the culture forward.”

— Dapper Dan, designer, chairman of the 2025 Met Gala

milan, italy june 19: giuseppe santoni attends the presentation of the santoni ss 2023 collection during the milan fashion week s/s 2023 on june 19, 2022 in milan, italy. (photo by jacopo raule/getty images)

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“Buying shoes isn’t just buying shoes. It’s buying a piece of happiness.”

— Giuseppe Santoni, president and chairman of Santoni

Guy Aroch

“Buy a nice big bowl, put it near your front door, and drop your phone in the bowl when you get home. Leave it there. Enjoy your evening of freedom.”

— Michael Sebastian, editor in chief of Esquire

a figure with a striking hairstyle is posing in a dark theater setting

Theo Le Foll

“I don’t just pack clothes; I pack characters. Think Rick Owens meets Mugler, with a splash of sci-fi seduction. I pack pieces that make me feel cinematic.”

— June Ambrose, creative director, costume designer

Matt Seidel

“One of the unsung joys of packing for a trip is being forced to edit your choices. Yes, I, too, purchased those jeans from that designer, but they would stay in my closet, and I would grab the more versatile pair every time I packed. I would depart with a tightly edited and versatile capsule wardrobe. I don’t need eight pairs of jeans in various shades; a medium-wash one works great. One day, as I began my umpteenth trip, pulling the same classic pieces out of my suitcase to get dressed, I realized that my personal style is what I pack.”

— Jeremy Kirkland, host of the Blamo! podcast

person reclining on a wooden plank on the ground

Joseph Echenique

“When I’m building a look, I explode the idea so it’s too big, almost unmanageable, then reduce down till it feels balanced. But always start with too much, to be able to take it back, otherwise you never know what angles you could have missed along the way.”

— Hamish Wirgman, stylist

a man examining various styles of shoes on a display table

Nick Sullivan

“Jet Lag Sandwich. Before an overnight long haul, buy your favorite sandwich at the airport. On arrival, put it in the fridge in your hotel room. When you wake up in the middle of the night with jet lag, eat it. Way better for getting back to sleep than gawping at your phone.”

— Nick Sullivan, creative director of Esquire

Apple Music

“When we decided to launch three new stations, I encouraged my friends at Apple to dedicate one offering to a Chill station. I can’t explain the kind of impact this new environment has had on me, but it’s another example of the beautiful frequency music can have over us and the way that a chance discovery can change our lives. We do a lot with our eyes these days. I am constantly amazed by the greater understanding of life and what is possible that comes from listening.”

— Zane Lowe, global creative director and lead anchor at Apple Music 1

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Jenny Walton

“Even if it’s ultimately simplistic, a layered style is always better. In the same way that my favorite homes have a lived-in mix of photos, paintings, and ornaments, great personal style has an authentic individuality.”

— Jenny Walton, artist

BLADI CORNIEL

“My best piece of advice as a creative would be to always embrace fear. On the other side of fear, there are rewards that you would never imagine for yourself.”

— Bladi, creative director, film photographer

a person standing sideways wearing a patterned brown blouse and black pants

NASIR CUMMINGS

“Aim for waves instead of having one viral moment.”

— Zhamak Fullad, director, film photographer

Steck Studios

“Vintage shopping is most exhilarating after two cocktails. Time is precious when traveling, and a drink helps cut the anxiety and the hidden cost of overthinking. Embracing rash decisions and listening to your lubricated intuition is part of the fun.”

— Alfonso Fernández Navas, senior fashion and market editor of Esquire

James Scully

“After 40 years of work travel, much of that time spent tracking missing or lost luggage, I gave up checking my bags. In one carry-on I pack my favorite clothing and a pair of sneakers. I wear good shoes, some extra layers, and one piece of outerwear on the plane. I carry an extra-large tote for my toiletries and computer, with plenty of room left in case I want to buy new things. And I gain an hour or more in both directions, completely relieved of the stress of waiting for a bag that may or may not arrive.”

— James Scully, cofounder of Jamestown Hudson

Barbie Beach

“Trends fade, but I stick to what sparks joy. I’ve trained my algorithm to serve inspiring creatives, sharp business insights, and the richness of African and Asian art. Pure bliss.”

— Barbie Beach, marketing manager of WGACA and Vintage Maven

David Casavant

“Anything you buy you should plan to own and wear for the rest of your life.”

— David Casavant, fashion archivist

miami, florida december 03: matt zingler attends richard mille after dark at wayne cynthia boichs art basel party in partnership with jetcraft on december 03, 2021 in miami, florida. (photo by bryan bedder/getty images)

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“You can tell if somebody is comfortable in what they’re wearing just by their mannerisms, which is why it’s really important that you just be you.”

— Matt Zingler, cofounder of Rolling Loud

Thalia Gochez

“Never thrift on an empty stomach.”

— Thalia Gochez, photographer

milan, italy september 20: maurice kamara attends the gucci women's spring summer 2025 fashion show during the milan fashion week womenswear spring/summer 2025 at triennale di milano on september 20, 2024 in milan, italy. (photo by stefania m. d'alessandro/getty images for gucci)

Stefania M. D'Alessandro

“Dinner at Waly-Fay in Paris and shopping at Selfridges in London. There’s nothing like shopping in Europe, especially with the savings and tax benefits. It’s more than just a pastime; it’s a passion and something that keeps me inspired while I’m away from home.”

— Maurice Kamara, founder of the People Gallery

person seated in a contemporary chair wearing casual clothing

CAITLYN MARTINEZ

“Invest in your dream jacket. You must have a good pair of raw denim. Black boots any time of year are always hot. If it looks right, it’ll feel right.”

— Caitlyn Martinez, stylist

Louis Ferc

“Decisiveness, intention, and repetition create the structure for your ideas to become a reality.”

— Stephanie Perez, stylist, art director

Frederik Lentz Andersen

“My conclusive method of choice for beating jet lag is to enjoy a light meal before boarding my flight, drink only still water during the flight, and upon arrival enjoy a meal fitted to the time of day in the destination’s time zone. This is obviously the pious and correct approach. But I’ve found that for the jet-lag recipe to work, it is of the utmost importance to complete both chapters. Chapter two is going out, getting completely shit-faced, and staying awake till you pass out.”

— Frederik Lentz Andersen, photographer, co-owner of the Copenhagen-based creative bureau Holidays

LORENZO SODI

“Never trust a suitcase that looks new. The best trips—and the best style—come from the wear and tear of real life.”

— Max Poglia, designer

James Emmerman

“If you’re struggling creatively, go to the movies. But not a theme-park movie. Get Mubi Go. Watch something weird. Take what you see back to your practice, whatever it is.”

— James Emmerman, photographer

Keith Oshiro

“Less is more. Wear a uniform, bring a camera, and be present.”

— Keith Oshiro, photographer

ROVI LUCCAI

“Finding balance in life often involves stepping into green spaces, particularly botanical gardens, to reset and reconnect. The Botanical Garden of Lucca is one of our favorite escapes. For anyone visiting Lucca, we’d highly recommend stopping by Taddeucci, a café opposite the Piazza San Michele, for an excellent coffee and a slice of their incredible buccellato Lucchese. If you’re after a true taste of Tuscan tradition, book ahead and try garmugia, a traditional Tuscan soup, at Buca di Sant’Antonio.”

— Bradley Seymour and Fabrizio Taliani, founders of Rovi Lucca

ZACHARY WEISS

“After years of poor purchasing, I’ve learned that before buying any item of substance—clothing, artwork, furniture—you need to feel something. It’s easier said than done, but it’s a split-second gut reaction to the ‘thing’ you’re eyeing. If you don’t encounter it, you don’t need to purchase that thing. If it’s above a certain price point—say $1,000—sleep on it, and if you think about it when you’re having coffee the next morning, go get it.”

— Zach Weiss, magazine writer

ALESSANDRO SQUARZI

“In today’s new things, you don’t find the beauty that existed in those that were new yesterday.”

— Alessandro Squarzi, creative director of Fortela

ASAKE

“Never force the vibe. That goes for music and fashion: If it doesn’t feel natural, it’s not for you. Find your groove and own it.”

— Asake, rapper, singer-songwriter

PETER MALACHI

“Traveling frequently has trained me to be smart with minimal packing. The trick is bringing along a couple of scarves to transform outfits with a bold, fun print. Same with ties. There’s a four-color knit tie that allows you to travel with one or two ties that give four to eight different looks. Why not?”

— Peter Malachi, head of communications at Hermès

fashionable individual posing on a busy street

RUEBEN LARKIN

“Style isn’t about money; it’s about taste. The best pieces are waiting in charity or vintage shops if you know where to look. It’s more exciting when you find something cool—and even better knowing it’s one of a kind.”

— Reuben Larkin, model, Internet personality

CHERYL GORSKI

“There’s a phrase you hear a lot in the equestrian world, that a horse should always be ‘clean and well presented.’ That strikes me as good basic policy for your average human as well.”

— Guy Trebay, reporter and critic at The New York Times

KATY GRANNAN

“For its museums, shopping, and brasseries, Paris is still my favorite city. I am not hip with restaurants: Arpège for romance, and Le Duc or Voltaire with close friends. Loulou, with its Casa Mollino–esque interior to share a lemon pizza late at night. During the day, rather than sitting for long lunch, seek out a Japanese Parisian bakery on the run.”

— Jeanne Greenberg Rohatyn, founder of Salon 94

ANNIE BERCY

“Kill the part of you that thinks you’re cringe.”

— Annie Bercy, film director

a posed individual wearing a black sweater and showcasing a wristwatch

KARL FERGUSON

“Being a native New Yorker has taught me to view celebrities like any other person. I tend to approach them with human empathy for often being treated like a commodity. That genuine intent as a photographer for me translates in the images.”

— Karl Ferguson, photographer

Courtesy of Zegna

“There’s a feeling that strikes me every time I experience it—the emotion of seeing something beautiful for the very first time. Like trying on a refined silhouette or discovering a perfect combination of colors you’ve never worn before. It’s spontaneous, almost magical, and it only happens once. The next time, it’s never quite the same. When I design new garments or create new silhouettes, I’m always chasing that elusive spark—the magic of the first time.”

— Alessandro Sartori, artistic director of Zegna

MICHELLE GRACE HUNDER

“My number-one trick of the trade for food in L.A. is Courage Bagels.”

— Ruel, singer-songwriter

a person in outdoor attire standing in a tropical setting

Robert Spangle

“Keep your phone in your pocket. Or better yet, keep cab fare and your hotel’s business card in your pocket and leave your phone in your room.”

— Robert Spangle, journalist, designer of Observer Collection

LUKE SILBERT

“When in doubt, size up.”

— Jake Silbert, director of news at Highsnobiety

a person sitting on a black couch talking on a pink rotary phone

Courtesy of Willa Bennett

“If there’s one thing I’ve learned, it’s this: Your personal style is your power statement—not just in what you wear but in how you move through the world. The most magnetic people I know dress and live in a way that feels deeply true to who they are. My best hack? Never wear anything you don’t want to wear. Life is too short.”

— Willa Bennett, editor in chief of Cosmopolitan and Seventeen magazines

milan, italy june 17: antonio de matteis attends the photocall ahead of the kiton ss24 men's presentation during the milan menswear spring/summer 2024 at palazzo clerici on june 17, 2023 in milan, italy. (photo by stefania m. d'alessandro/getty images for kiton)

Stefania M. D'Alessandro

“In all things and in every field—be it fashion, food, or travel—I firmly believe that quality is always the key. Quality always pays off: in the product, in innovation, in service, and, above all, in people. The real secret? There is no secret. It’s quality that speaks.”

— Antonio de Matteis, CEO of Kiton

Chris Fenimore

“The longer I write about clothes, the more valuable I realize ‘investment’ pieces are. Not because of any kind of financial calculation but because the longer I have something of quality, the better it looks and the more I love it. It becomes an emotional relationship.”

— Simon Crompton, founder of Permanent Style

a welldressed man seated on a leather couch exuding a sophisticated atmosphere

LORENZO SODI

“No trip to Florence for me is complete without visiting a tailor, although I am technically not at work.”

— Douglas Cordeaux, joint owner of Fox Brothers

individual standing on a wooden dock by a body of water

ISAAC MARLEY MORGAN

“Have a first-evening ritual. If I’m ever lucky enough to find myself in New York, I like to make my way to Minetta Tavern, an institution over on MacDougal Street that I’m sure you’ll have heard of. I’ll sit at the bar, order a burger and maybe a martini, and then I’m on my way. It’s nice to have some familiar habits during a trip away.”

— Michael Hill, creative director of Drake’s

Cory Vanderploeg

“When traveling, whether for work or pleasure, I relish in having a solo dinner at a bar of a restaurant, preferably one that is an interesting scene or on the ‘hot’ list. It allows the time for me to relax, process the day, think about what I saw and who I met, and properly appreciate those experiences. I often bring a magazine to read and try to avoid the temptation of the phone.”

— Bruce Pask, senior editorial director of Neiman Marcus

Isaia

“Trends expire. Personal style doesn’t. If you feel great in it, you’re already ahead of fashion. Your style should move like your soul—never fixed, always evolving, and unmistakably yours.”

— Gianluca Isaia, CEO of Isaia

Emily White

“I used to watch wrestling when I was younger and Ioved that they would wear belts when they won. It expressed winning and championship and they would wear it with pride. It’s why I love cool, fancy belts. Fashion is a thing you live. To wear clothes is to wear your identity.”

— Jordan Adetunji, rapper, singer

UTA

“When I travel, I always wear my bulkiest items—think jackets, boots, the whole nine—to save space in my suitcase. Pro tip: Stuff your socks, underwear, and tank tops (essential) into your shoes to make the most of every inch.”

— Bloody Osiris, creative director

esquire

Life-Changing Advice from 50 of the Most Interesting People We Know

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Life-Changing Advice from 50 of the Most Interesting People We Know