It may be my third extended stay in Thailand’s mega-city capital, but Bangkok remains an enigma. An enigma with familiar parts, no less – the treble revving of tuktuks as they weave through traffic, the potpourri of roadside delicacies pervading every street, the oppressive heat quenchable only by an ice cold cha thai yen. Reluctant to part with the momentary respite the BTS provided from the noontime sun, I alighted at Phaya Thai station – two stops away from the tourist-clogged Siam interchange. No glitzy malls visible from the platform here, but according to the friends I was meeting for lunch, there’s a “nice Thai place” with great local food.

With a lilting hellooooo! Boonsiri “Mai” Chutidamrongpan, a bubbly English teacher at a public school, snapped me out of my bafflement with the many signs overhead. After a quick hug we exited the station, and five minutes into our “short walk to the nearby restaurant” I had to ask in all my schvitzing glory – just where are we going? She assured me it was worth the jaunt, that the place was “very hipster”, and that we’ve got a table outside. What?!

Part Paris bistro, part biergarten, Bangkok Heritage was packed with young, good-looking guys and gals. As I walked – no, as Mai dragged me through the air-conditioned interior and out onto the patio, I quickly understood the “hipster” appeal. Surrounded by gardens with pavers and low walls bordered with luxuriant Christmas palms and banana saplings, a clapboarded house stood in the large courtyard, lifted off the ground with 8-foot tall pillars. The other friend I was to meet, Palaboon “Boom” Daoruang, sat at one of the tables under the house, looking all cool (literally, too) in a green unmarked polo and taupe chinos. Boom, now a co-producer at Thailand’s liberal news channel Voice TV, is a close friend of Mai’s.

As we updated one another about our lives over som tum thai kai kiem, stir-fried morning glory and refills of coconut juice, the word “hipster” kept cropping up. Perhaps it’s a Thai thing, but I couldn’t believe how pervasive a standard “hipster” has become with which to judge everything – way of dress, restaurants, shopping areas, universities, even how you take a selfie. If you wear prints, you’re obviously mainstream. If you shop at Jatujak market, you’re behind the curve. Jatujak Green? Better. Artbox or Train Market Srinakarin? You’re full-blown hipster! Especially if you get a burger from a food truck while picking greens out of a mason jar. Unable to contain my fascination I pointed at the orange kaeng som and asked: is this hipster, since it’s not the usual tom yum?

Just as we burst out in laughter, a group of teenage girls gathered in front of an unfinished concrete wall for a photo. Perfect timing – I was about to witness a live demonstration of hipsterdom. None of the girls looked at the camera, none of them smiled. Each of them had an insouciant pose, nothing obvious or ANTM. No matter that a few of the girls had Chulalongkorn University uniforms on; as long as there’s a horticultural background or interesting textures and architecture, you’re fine. Oh, and don’t forget the skewed camera angle. “Your Instagram’s very hipster, no faces!” Mai exclaimed, as she browsed my feed of willow trees and black-and-white landscapes. Apparently the fewer faces on your Instagram, the higher your hipster cachet.

Sometime after that delicious and educational lunch, I remember coming upon a short interview with a local rocker on an English-language men’s lifestyle magazine. His name escapes me, unfortunately. I do remember, however, his grungy long hair, undeniably stylish looks, and one comment that hit me hard: “I don’t wear suits because that’s so mainstream. I hate mainstream.”

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Separated from the eastern coast of Florida by waterways just south of the Georgia border, Amelia Island is a scenic locale that’s a mix of lush marshes, Southern charm, and classic car concours d’élégance in country clubs. It’s the tail end of summer, and I’m in town to see family.

It’s a ritual of sorts to visit Ms. Carolyn’s, a popular local pancake house in the middle of a strip mall. It’s early on Saturday morning, and a cacophony of drawly greetings, kids playing, and omelettes sizzling on the pan fills the simply furnished joint. Sitting at the adjacent table was what most people on the coasts would write off as a true Southerner – a very large man, dressed in a reef tee and baggy floral shorts, sandals on his feet. Most striking was his enormous beard, coiffed à la Verdi.

Granted, he looked rather gauche. Or even ridiculous. But his beard really got me thinking: transplant it on a West Coast creative, and you’ve got an ironic hipster statement. Especially if it were paired with suspenders and full-colour sleeve tattoos. The question is, though, who’s really the one being himself? I ask that only because hipsters claim they dress and behave differently because they don’t conform to the mainstream. Everyone is inherently different, they say.

Not to paint all West Coast hipsters with the broad brush of phoniness, but more likely than not the guy trying not to soil his oversized beard while he sips his soy macchiato sweetened with Stevia would eventually get rid of the beard in favour of the next facial hair trend GQ “discovers”. And you know the guy in Ms Carolyn’s would still have his. Probably always will. So who’s the real hipster now?

Lauding something simply for being hipster inevitably empties it of its worth. The value of doing, wearing, or saying something should be inherent (to borrow a verse from the hipster bible), independent of its acceptability in society. Suits should be frowned upon because they’re “mainstream”? What if wearing a suit makes me feel absolutely at home? Alas, hipsterdom is not some liberating lifestyle – follow the rules and you’ll look like you’re being yourself! – it is an orthodoxy with its own litany of rules, as I learned on a hot summer’s afternoon in Bangkok, and from living in Los Angeles. That’s the unfortunate meaning of being hipster.

This is why at HSD we don’t have much love for rules. Slapping on whatever is sanctioned by the hipster “in-crowd” (ironic, I know), or by the mainstream for that matter, isn’t going to make you happy. It’s so much easier to shop for looks and make style choices once you know who you are and what you’re comfortable with. It’s going to look more authentic this way, and you’ll feel more confident in your outfits too. The BoHipster, as we call it here, is certainly a construct that’s historical and worthy to emulate – but it’s merely one archetype in the vast spectrum of menswear. Menswear is so much more, and style shouldn’t just be an opposition statement against the mainstream. It should be about you first.