This month in Après Diaries, we are spellbound by Jessie Webb. A master of taste, time, tunes and tinkering, Jessie is the arbiter of all that is lush, and the facilitator of all that is fun.
The world sounds and looks better on this side of the fence; come and join us.
To properly introduce you, what are your nicknames?
My name is Jessie, but I have a few names. I went to boarding school when I was 11 and, overnight, became Jess. That stuck for about 10 years. At some point, I rebranded back to Jessie.
When I moved to Melbourne, I met my best friend Claire, who started calling me Wessie. Now it’s universal. My mum, my friends, their kids, they all call me Wessie.
My sister Maitland calls me Yayar. The lore is that we watched a TV show called Wimzie’s House as kids, and the main character lived with their grandmother, Yaya. I don’t think she has ever called me Jessie. She’s 30 and still calls me Yayar. I’m choosing not to be offended that I was clearly the overbearing grandmother figure to my younger sister, but it’s something that belongs just to the two of us.
In three words, how would your closest friends describe you?
I called up the gang for this one. Highly recommend asking your friends this, maybe once a year, like an emotional audit. I read their answers and felt like I was being kissed by a thousand labradors.
A drop-anything-to-help, ride-or-die girl who loves as big as she cares.
Style-forward, culture-led, and always knows what's happening in the best corners of the internet.
Extra fun, extra giggly, maker of the best salads money can't buy.
Just as likely to kill a live snake and know how to bridle a horse as she is to show you where to get the best socks and Japanese cookware.
Where do you currently live, and with who?
I live alone in a 70s flat in Brunswick West. It’s filled to the brim with everything I’ve ever hoarded in this life. It’s old and full of quirks, and I find myself apologising for it when people come over, but in reality, I love it because of them.
Do you love it there?
It feels like my shell in a way, somewhere I can retreat to and de-frag. Feeling comfortable in my space is incredibly important to me.
The dream is to eventually move to West Gippsland, where my family has deep roots. Live on the cliffs with a heap of labradors, a Land Rover, maybe a piggery. Think Queen Lizzie of Phillip Island. Watch this space.
What do you currently do for work?
In short, a bit of everything, which is how I’ve operated for a while now.
I work a few days a week for a New Zealand fashion label, a few days in a design-forward general store, and the rest of the time I’m building out my photography practice. Every week looks different, which I’ve realised is exactly what keeps me going.
My background is in fashion sales and customer experience, and that bleeds into everything. I’m always thinking about people, how they move, what they respond to.
Coffee order?
I’m a cold beverage girlie. Iced latte, iced matcha, and I try to keep my caffeine intake somewhere between operational and completely out of control.
When I first moved to Victoria, people seemed to think ordering an iced drink in winter was completely insane. Personally, unless I’m ankle-deep in snow, there’s no reason not to put ice in my cup.
What are your favourite sounds?
Falling asleep at my mum’s house and hearing the Bass Strait crashing against the rocks.
I grew up around helicopters, so when I hear one in the distance or overhead, it always makes me think of home.
The squeals my mum’s dog makes when I arrive - very high-pitched, very emotional.
Do you have any self-imposed rituals?
This is something I’m trying to build out more. There’s so much conversation around ritual and ceremony, but for me it’s really about consistency.
Swimming laps at my local pool.
Driving down to my mum’s farm, long baths, ocean swims, collecting rocks.
My skincare routine is probably the easiest way for me to wind down at night, and I’ve recently started red light therapy, which feels slightly futuristic but calming.
And incense, always incense. I’ve been known to take it to the beach and have been absolutely roasted by my friends as a result. I don’t really see the issue with creating a bit of atmosphere.
What’s one skill you’re currently learning?
Japanese. I’ve spent a lot of time in that beautiful place and have half-committed to learning the language for years. Now I’m in my third semester and trying to actually absorb it all.
It’s been quite challenging, and there have definitely been moments where I’ve wanted to abandon it, scurry home, and binge-watch The Office for the hundredth time. But I’m pushing through and feeling proud of myself.
Is there anything you’re currently unlearning?
Completely. I think my version of adulthood is mostly unlearning.
My early thirties have felt like a quiet reset. Some health challenges have forced me to slow down, which hasn’t been easy, but it’s made me more aware of my patterns, especially how hard I can be on myself. I’m learning to zoom out, pull back, and sit with things instead of pushing through them.
It’s less about fixing everything and more about understanding myself, having a bit of grace, and moving with intention.
If you could only listen to one album for the rest of time, what is it?
This is an impossible question, but I’d say The Renaissance by Q-Tip.
I found it at a really formative time. The people I lived with and the community around me were creative and encouraging, and it’s when I started to find confidence in myself. That album opened the door to so much of what I still listen to now.
It’s stayed with me, so it may as well stay forever.
What’s your death row meal?
Another impossible question. I could spend a lifetime building this menu.
But if I’m on the chopping block tomorrow…
Sashimi moriawase, ideally omakase if the executioners have the time.
A freezing cold, dirty martini, three olives.
Steak frites with peppercorn sauce, dressed leaves.
A small intermission.
Cheese, cured meats, grissini. A thin cigarette. Campari soda.
If I’m allowed a nap, that would be ideal.
Then a long, drawn-out yum cha or an enormous Korean feast. Friends in attendance, even if they have to sit behind the glass and watch, we can make it work. Maybe everyone tells me their three favourite things about me before I’m sent off.
Also, I’d rather not go out via a needle, so if the food is quietly poisoned towards the end, I’m actually fine with that.
Favourite items in your wardrobe?
A Story mfg. checkered dress that makes me feel like myself, a pair of Marni mary jane sneakers that go with everything, and a small Porter-Yoshida bag that I can fit a serious amount of stuff in.
What never fails to make you excited?
Sharing meals with friends.
I feel incredibly lucky with the people around me. They hype me up, understand my quirks, talk me off ledges, roast me when needed, and push me forward. There’s something about being around them that resets everything.
What never fails to make you freak out just a little bit?
Life, honestly. I run pretty close to the surface most of the time.
I feel things quite deeply, which is a strength, but it also means I can spiral a bit or get ahead of myself. I’m trying to stay more with what’s actually happening, rather than what my brain thinks might happen next.
And needles. I absolutely hate needles.
What does your perfect day look like, from start to finish?
I wake up (god willing) and have a long laze in bed, scroll my phone, ideally a few friends have texted me their three favourite things about me.
Put a load of washing on. Go get a coffee, maybe a bánh mì or a chicken rice situation.
Come home, incense on. The washing is done (I have a clean washing kink). Online purchases arrive, they fit, I love them, no returns, no disputes, no lessons learned.
Afternoon is a swim, sauna, or ocean dip. Then another small laze, something fizzy in hand.
At some point I’m either out tending to my cattle, loosely overseeing the land, or letting my six labradors run wild along the cliffs. Wind in my hair, absolutely no real responsibility but a strong sense of ownership.
Then I come back to reality, slightly salted and sun-tired, and the evening is spent sharing a meal with friends or a lover.
That’s the perfect day.
Hear the sounds of Jessie:
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