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James Reid Wants You to Stop Trying So Hard

Esquire Philippines sat down with the Careless Music founder on his most stylish record yet, getting dressed like he makes music, and why trying too hard bogs you down.

JV Ordoñez

by JV Ordoñez

Published on Sep 11, 2026

My first brush with anything James Reid or even becoming aware of his existence was when my older brother played the cult classic "Bahala Na" on the family stereo, and I don't really know if you can call that serendipitous or not.

Even back then you could feel this cultural penetration from that first "Naniniwala na ako sa forever" he sang, or his noble advocacy to beat this "energy gap" epidemic circa 2016.

Fast forward many more years, and the Careless Music founder's metamorphosis had already taken shape by the time I eventually had this conversation with him at the Admiral Hotel's Presidential Suite in Manila.

Mr. Reid was surprisingly effusive in pulling back the curtain on his style philosophies as your neighborhood's divisive renaissance man who doesn't need a blueprint to ooze cool.

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James Reid dripped out in Genes and Hails

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Photo: Cyrus Panganiban

Inner: Pinagtagpi

Suit: Franz Javier

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Full outfit: Fendi

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Walking Off Unfortunate Style Choices and Trusting Your Gut

Being scrutinized under a microscope for most of his life understandably means he made bad style choices.

"You just have to walk it off. Don't look back. Just keep looking forward," he said in a cheeky way as he recounted the days of the deep V-neck and his stint with super spiky hair/emo fringes and other cardinal fashion sins he may have made under the spotlight.

"It's a whole ritual of me just feeling it out. There's no rhyme or reason. Sometimes I'll pick, 'Oh, I want to wear these shoes today.' And then I have to figure out the rest from there."

Reid added that it's adjacent to how he crafts music too: a balancing act of trying what to fit in sonic puzzle pieces of ideas he wants to make work.

"You always want to dress for the occasion; you always want to dress for the vibe. One always affects the other."

On whether Filipino men are actually getting more intentional about how they dress or are just sheeple following whatever nostalgia-baiting trend is hottest, the creative extraordinaire gave a pretty lucid take about everything.

"We go through phases of bringing back older styles from different eras," he said.

"I think it's us sifting through the things that worked and didn't work. We go back to Y2K, but we don't pick up everything from that era. Just the things that really worked. People have access to so many different options now, so it becomes more personalized."

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Photo: Cyrus Panganiban
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Sitting across from him, the record label owner and actor, true to his word, didn't strike me as someone who hypothesized which clothes went with which and felt like someone who went on unadulterated instinct. And I can't really blame him for this sensory style situation if it works for him.

Don't ever expect Reid to be the type to be on the losing side of a so-called "swag gap" in a relationship, that's for sure.

This universal ethos stemmed from a masterclass in philosophy from his vocal coach in LA: "Stop trying to sound good. Stop trying to look good. Just go and be as free as possible."

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Yeah, Stop Trying

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There's this phenomenon online called the "LARP," or "LARPING," which stands for live action role playing. If you have better things to do than to doomscroll, this just translates to people being posers in the vertical age of Instagram Reels and short-form content that dictate whatever's in fashion.

Reid's poignant new motto is as real as it gets and is a sign for you to stop being performative with how you dress or to rid yourself of the desperation in trying to prove that you have respectable taste.

He took this with him after that one vocal booth session and has been applying it to everything since: music production, styling himself, and running a label that's had more rough patches than the rose-tinted expectations you usually have with overseeing an operation of that magnitude.

The singer's latest record, Honey, I'm Home, is his cathartic expression of freedom in his own skin and how love shifted his perspective on the multi-faceted life he lives.

Taking his newfound vision on freedom, the former local teeny-bopper is coming into his own and has found a home in music.

"Just try and sound as free as possible," Reid said.


"Then you're going to sound good. And I think it applied to more than just singing. It applied to music. It applied to literally everything in my life."

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Coming of Age in Public, Switching Gears

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Reid is unsurprisingly quite a polarizing and often misunderstood component in local show business. To me, he's going through a potentially similar pivot as Canadian pop star turned swag overlord Justin Bieber, who resorted to reinventing his style and music into something much more raw and a far less artificial with his Swag duology of albums as he found the sauce with glitchy sonic wizards Dijon and Mk.gee. We can't get enough of these two and their influence on the current music landscape.

This culminated in his blockbuster headlining set at this year's Coachella music festival, which was mostly met with praise other than the folks who weren't amused by him messing around with his laptop on stage to karaokify his greatest hits.

Both Reid and the Biebs came of age under intense scrutiny and animosity under the court of public opinion.

The Fil-Australian musician admitted that throughout most of his arcs in his life—Pinoy Big Brother, Love Teams, and now his foothold in the music industry—the limelight scrambles your marbles quite a bit.


"I'm not going to lie. It messes you up in the head a little bit," Reid said candidly.

He attributed his maturity mostly to his father's guidance and grounding, which developed his existing humility as a man.

"Whenever I started to show an attitude, he'd be like, 'No, don't be like that.'" People are just trying to make you happy. He would always give me an ego check."

Reid summed it up by saying he stopped caring about what a lot of people were thinking and saying, leading to him carving his own path and making peace with the choices he made and was eventually going to make.

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He's Home

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Now we get to the nitty-gritties of his latest record, Honey, I'm Home, which is quite the pristine album with Reid's candid influences of the aforementioned Dijon, Mk.gee, and the Bieber sonicverse apparent in the production executed in a fresh way.

This is quite obviously his most honest album if you look at songs like "Unbecoming," where he recognizes his shortcomings as someone who is hard to love, all over tastefully beefed-up guitars with and layered vocals with that throwback R&B filter that you usually can't go wrong with.

Songs like "Attention" and "All Night" feat. Arthur Nery and "Sunny Side" with Luke April from PLAYERTWO fame were genuinely stunning cuts from the music exec that made me scratch my head a few times in astonishment. One of those rare moments when you listen to an album that made me say, Mr. Reid, we weren't familiar with your game."

"What came out of it felt very me still. It felt like an evolution of everything that I've done before," he said, commenting on what encapsulated making the album feel like.

"What inspires me are life experiences—making mistakes or messing up or something really awesome happening in my life. I put a lot into philosophy too."

I guess we should take it from the enduring style savant/vibe merchant: screwing up is the best way to lock in a groove if you actually listen back to the tape.

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Story and Interview: JV Ordoñez

Production: Rhia Grana

Editor-in-Chief: Paul John Caña
Photography: Cyrus Panganiban

Videography: Jino Del Mundo
Creative and Design Direction: Igi Talao
Hair and Makeup: Muriel Vega Perez
Head Stylist: John Lozano

Associate Stylists: Lon Morelos, Arar Pascual
Special Thanks To: Admiral Hotel

JV Ordoñez

Esquire PH's resident music scribe, wristwatch disciple, and essayist fluent in niche internet subcultures and Philippine politics.

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