Why there is no such thing as overdressing

 (NurPhoto via Getty Images)
(NurPhoto via Getty Images)

In fashion, what is frozen out is never far away for long. Look at Gen Z colonising every ‘mistake’ you made circa 2002. Think you’re permanently post-pink following the big Barbie binge of ’23? Sure, until next time…

And good news for the skinny jeans stalwart: Hedi Slimane says you can once more restrict the circulation from the waist down. And yet, despite the Hokey Cokey of the zeitgeist, one constant sartorial diktat remains firmly ‘in’: it is always better to be underdressed than overdressed. What each of those actually looks like is defined entirely by context. So, you can of course be badly dressed at the Oscars — but you cannot be overdressed. Also, a look can be capsized in under/over territory by the slightest shift. Jeans might be on-point for the office, but imagine your same safe-for-work denim, just ripped? Now you’re underdressed.

So, yes, what we mean when we say under/overdressed is more about an attitude, a concept, than a specific look. Underdressing = casual to the point of laissez faire; overdressing = gauche, pathetic, ignorant, deaf to the social nuances around you. It’s a choice between acting like a dick and looking like one. Why do you think loungewear became such a flex for the tech bros who run the world?

Season-whatever of The Real Housewives of New York City is currently airing. In it, Jenna Lyons, the former J Crew creative director and president, and member of the entirely rebooted cast, wades in. ‘I love someone who overdresses. It makes me happy. Like, if everyone was perfect and normal all the time it would be boring.’ (FYI: she says this while wearing pearls and a tie in a confessional VT).

This musing is pronounced in reaction (or at least the edit makes it look like it is) to a fellow Housewife, influencer Sai De Silva, turning up to a wreath-making class in head-to-toe white and sunglasses. I admit I am tragically not au fait with what is the dress code in the festive decoration cottage industry of Manhattan, but what she is wearing doesn’t scream overdressed. She’s in sneakers, for one; she’s in a Real Housewives, more importantly.

But I get it. It’s too considered, too thematic, it looks contrived. The implicit ick of overdressing is that it implies trying too hard. That’s how I ended up having dinner in The Wolseley with an ex in trackpants or not owning a hairbrush in my early 20s; I was terrified of looking like I was too eager to please. But I am a reformed underdresser; and it is the effortfulness that makes me love it. It feels honest. There is something transparent, guilelessly authentic about visibly making an effort. About trying. Life does require graft. What’s exhausting is to pretend it doesn’t or to try to be on just the ‘right’ side of underdressed; the French or Californian side of underdressed rather than the PJs-in-Asda underdressed.

So, on my shopping list this season? Thigh high Bottega Veneta boots, 16 Arlington crystals, Simone Rocha’s gold coat, Alaïa’s whipstitched leather dresses. All for day. Call it overdressed if you want, but I’ll be calling it sticking it to the man — in style.