My personal rules for dressing
Never be a tree
I have probably mentioned it here before but when I’m not working, parenting, or cleaning mud from the garden off the dog’s feet - I enjoy mindlessly watching people (mostly men) on YouTube give (mostly bad) style advice.
I also consume lots of well-considered, good quality content1 about clothing and style, but — similar to reality TV — it’s the bad stuff I usually enjoy the most.
The videos often take the form of lists of rules to follow. Here are mine. They apply only to me.
Don’t be a tree.
Be careful with brown trousers and green tops. Both elements are great on their own but combined, you’re instantly a tree. Or Shaggy from Scooby Doo.
I’m relatively tall so maybe it’s a height thing. But then again, if you’re short: shrub.
Don’t be a ballerina
Close fitting black undershirts are fine on most people. But unfortunately for me, when I look in the mirror, I can’t help but imagine I’m wearing a dancer’s sexy black leotard as a base layer.
No rugby jerseys as casual wear
This one hurts, because I also think that the rich-country-boarder-at-Sydney-private-school aesthetic is the cuntiest and coolest look of all time. Australia’s answer to Ivy Style.
I like rugby jerseys, but it’s too close to my preppy roots and feels like I’m cosplaying a version of myself that took an only-slightly-different path.
The same goes with Polo Ralph Lauren polo shirts, pale blue gingham, pastel blues or greens, the Country Road duffle bag, a few particular shades or beige chino, spread collars, any popped collar, linen shirts where the linen is thin and the hems curl up revealing belly and all Havaianas.
Strangely, all forms of boat shoes and Canterbury Rugby shorts get a pass.
No black shoes
Except for black tie or a funeral. I’m not sure exactly why - maybe too high contrast with the rest of me.
No hoodies
This one is a shame. I have tried so many times, but whenever I put one on and look in the mirror it feels like I borrowed someone else’s torso.
No sneakers/trainers outside of exercise
I use to always covet sneakers as objects and then never wear them or quickly tire of them. They didn’t make me feel like a special little boy so I cut them out of my life.
Jeans should look like they look on Wayne and Garth from Wayne’s World, Jerry Seinfeld, Elaine Benes, Axel Foley from Beverly Hills Cop or Bruce on the cover of Born In The USA
The problem is, none of these people cared about their jeans. They just went to the shop and bought them. That’s why they look cool. So having saved eBay searches for every variation of “Made in US Levis 505 orange tab w34 l32 70s 80s 90s” is sort of counter to the point even though you do it anyway.
Caps should be very old.
If your cap is new, I recommend wearing it quietly in total isolation until it’s old. Charge your Airpods and listen to some podcasts or do the dishes to pass the years.
Important: you can’t take measures to artificially age the hat (cheating). And you also can’t buy a new hat that’s made to look old (unless you’re in Japan and see a cool Japanese person do it - that vetoes everything I’ve said).
Exercise clothes should look like painting-the-house clothes2
If you look slick and professional when you go running, it will be shocking to people how slow and inelegant you are.
If you’re wearing your PE shorts from 1999 and a Crowded House Live At The Opera House t-shirt, people will presume that you maybe have a packet of ciggies in your pocket — and considering that — you’re doing okay.
If you are interested, I love the writing of David Coggins, Derek Guy, Rachel Tashjian, the comics of Dick Carroll and the general content of The Iron Snail and Edgy Albert.
I’ve never painted anything in my life