The weirdest life advice from the most interesting people we know (and why it works)

Everyone has a favorite piece of advice they never got around to following. This isn't that list. These are thirty small, oddly practical rules from designers, musicians, editors, and CEOs that are strange enough to remember and simple enough to use tomorrow morning.

On style, because how you show up matters

• Tim Little (CEO, Grenson): Keep your socks from being funnier than you are.
• Shaboozey (musician): Real style comes from mixing what's expensive with what isn't, and letting it feel unmistakably yours.
• Jenny Walton (artist): A layered look almost always beats a flat one, the same way a lived-in home beats a staged one.
• Matt Zingler (co-founder, Rolling Loud): People can tell when you're actually comfortable in what you're wearing, so just be yourself.
• Reuben Larkin (model): Great style is about taste, not money. The best finds are sitting in a thrift shop right now.
• David Casavant (fashion archivist): Before you buy anything, ask if you'd still want to own and wear it forever.
• Willa Bennett (editor-in-chief, Cosmopolitan & Seventeen): Never wear anything you don't actually want to wear, life's too short for the alternative.
• Gianluca Isaia (CEO, Isaia): Trends have an expiration date. Personal style doesn't.
• Guy Trebay (journalist, The New York Times): Borrow a line from the equestrian world, stay "clean and well presented." It's just good policy.

On travel, small tricks, big payoff

• Nick Sullivan (creative director, Esquire): Buy your favorite sandwich before a red-eye flight, refrigerate it at your hotel, and eat it if jet lag wakes you at 3 a.m., it beats staring at your phone.
• James Scully (co-founder, Jamestown Hudson): After decades of lost luggage, he stopped checking bags entirely, one carry-on, good shoes, and a tote with room to spare.
• Peter Malachi (Hermès): Pack a couple of scarves or a four-color knit tie instead of extra outfits, one item, several completely different looks.
• Rosario Toscano (CEO, Akoni): Carry your passport while shopping in Japan for the tax-free discount, and make time for the flagship Uniqlo in Ginza.
• Frederik Lentz Andersen (photographer): The "correct" jet lag cure is a light pre-flight meal and water only, but he admits chapter two of his real method involves staying out until you collapse.
• UTA (talent agency insight): Wear your bulkiest items on the plane, and stuff socks and underwear inside your shoes to save suitcase space.
• Robert Spangle (journalist, designer): Leave the phone in the hotel room. Take cab fare and the hotel's card instead.
• Michael Sebastian (editor-in-chief, Esquire): Get a bowl by your front door, drop your phone in it the moment you're home, and enjoy the rest of your evening.

On creativity, push past the obvious answer

• Hamish Wirgman (stylist): Start with an idea that's too big and unwieldy, then pare it back, you'll never know what you missed if you start small.
• James Emmerman (photographer): Feeling stuck creatively? Go watch something genuinely strange at the movies and bring what you see back into your own work.
• Bladi (creative director, film photographer): Embrace fear on purpose, what's waiting on the other side is usually better than you imagined.
• Keith Oshiro (photographer): Simplify everything: pick a uniform, carry a camera, and just be present.
• Jeremy Kirkland (podcast host): Packing for a trip is really an editing exercise, the pieces you keep grabbing, trip after trip, are your actual personal style.
• Alessandro Squarzi (creative director, Fortela): Something about yesterday's "new" had a beauty that today's new things haven't matched.

On money, taste, and knowing when to buy

• Zach Weiss (magazine writer): Don't buy anything of real substance unless you feel something instant and physical about it. Past a certain price, sleep on it, if you're still thinking about it over coffee the next morning, go get it.
• Giuseppe Santoni (president, Santoni): Buying shoes isn't really about the shoes, it's buying a piece of happiness.
• Simon Crompton (founder, Permanent Style): The value of an "investment" piece isn't financial, it's that the longer you own something well-made, the more you love it.
• Antonio de Matteis (CEO, Kiton): There's no secret to quality, it just pays for itself, every time.

On mindset, the ones that stick with you

• Annie Bercy (film director): Kill the part of you that worries about being cringe.
• Zhamak Fullad (director, film photographer): Chase steady waves of momentum instead of chasing one viral moment.
• Stephanie Perez (stylist, art director): Decisiveness, intention, and repetition are what actually turn an idea into something real.
• Karl Ferguson (photographer): Treat everyone, celebrity or not, with the same basic human empathy, and it shows in your work.
• Barbie Beach (marketing manager): Curate your own algorithm on purpose. Feed it what actually inspires you and skip the rest.
• Alessandro Sartori (artistic director, Zegna): Chase that spontaneous, almost magical feeling of seeing something beautiful for the first time, it never repeats itself quite the same way twice.

None of these require a life overhaul. Pick one, try it this week, and see which one actually sticks.