I’m one of those unfortunate souls in the old photo albums people are quick to point out. Mainly for what I’m wearing, but sometimes for the “frullet” hairstyle I entertained in my teenage years (that’s a front-mullet, if you’re curious).

I think my critical low point occurred 15 years ago when I wore a dress by an emerging designer, purchased at one of those design incubators in the bowels of the city, to the Year 11 formal. It was basically a cross-weave of bandage-like material spattered with blood-red paint and fringed at the hem with large white feathers. My closest friends still refer to it as the Dead Seagull.

Not exactly what I was pitching for. In my head I was directional, avant-garde, and borderline terrific. Like a Lady Gaga of the suburbs, before my time. Apparently not so.

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And fine, I’ll confess: the D’Seagull is not an isolated incident. There are countless fashion regrets in my repertoire of experimental outfits, and I can break them down into three categories.

Absolute catastrophes

The most woeful of all my faux pas peaks on two axes: the most ugly and the most expensive. You can sometimes forgive fugly one-offs if they are cheap-and-cheerful mistakes. Examples would be travel acquisitions; you return from South East Asia with bog-catcher pants and wrists piled with prayer beads, or from the US with lurid sports-team merchandise from that one game you went to. It rarely works when integrated into your customary wardrobe, but you can shrug off the bad investment with a degree of affection.

It’s when the style-trial is costly that the cringe factor really escalates. For me, one such episode occurred in January 2012 when I was seduced online (no, not in a chat room) by a pair of Missoni python-trimmed platform suede ankle boots. Coloured purple and green, replete with sparkly laces. I normally love anything Missoni (those chintzy Italian babes!) but these puppies were pretty garish, and pricey AF.

For the record, I’m not a closet billionaire (darn it), nor can I see where “psychedelic Sergeant Pepper boot” fits into Maslow’s Hierarchy of Needs. Yet I possess a condition that renders me periodically willing to outlay a stupid amount of money on items that would work better in a circus.

To add insult to injury, the Missonis were far too small, and on the three occasions I wore them I had to wear plastic bin-liners instead of socks just to get them on.

Honourable mention in this category has to go to rabbit-fur Muk Luk boots, handmade and embroidered by First Nations producers in Canada, built to survive the most brutal of winters (ie. not to be worn with shorts around Sydney in the springtime).

Highly regrettable

One thing that took me a while to realise is I am not Talitha Getty, arbiter of the hippie-de-luxe look and icon of the late 1960s. With alluring mystique she globe-trotted her way around various bohemian enclaves clad in kaftans, turbans, lashings of elaborate jewellery and bold eyewear. I fancied this vibe for myself: exotic, intriguing, worldly.

Thing is, if you are not blowing smoke-rings from a hookah pipe on a Marrakech rooftop, but you are dressed like you should be, then you kind of look like a ponce. And I have teetered into this zone on a couple of occasions. For example, I recall robing myself in an ankle length, leopard-print Muu Muu with a large frilly collar. Paired with a turban-y headscarf and some big-ass glasses. Maybe a toe ring.

My intent was to channel a character from a Slim Aarons photograph. In reality, I more closely resembled a new species of frilled-neck lizard wearing a swimming cap and goggles.

Misdemeanors

This type of offence includes partaking in any fashion trend that is too lame-stream. While individual bloopers are regrettable, to be a lemming is wretched. And what a fluffy sheep I have been, particularly in the early 2000s.

I’ve chosen to forget the fluorescent Roy jeans and micro-skirts; the Rosemin hanky-hem dresses; Alex & Alex kitten heels with long pointy toes; Bettina Liano spray-on denims with lacy buttock detail; Alexander McQueen skull scarves (popularised by LiLo, no less); and hobo handbags worn dangled from the elbow like a large testicle.

Other notables in this category go to the bell-sleeved paisley maxi-dress (Joni Mitchell-throwback attempt), the urban cowgirl outfits (cheers Sienna Miller, circa Jude Law), and the whole Von Dutch trucker-cap disaster (Paris Hilton and friends, be damned).

Research shows that trends last two to five years, declining once they reach saturation point and become ubiquitous.

Which is why destined for the same ash heap of history will be Isabel Marant wedge sneakers, Scanlan and Theodore peplums, and Off The Shoulder Tops. Mark my words, Dollies.

Michaela Davis has worked for global brands including Louis Vuitton and Moët Hennessy for more than 10 years. She is also a mother, on her L-plates, to a nine-month-old son.