How to Flex At Your High School Reunion

How to look more successful than your classmates.

Let’s be real. You knew it was coming.

Your wedding day, the birth of your child, the reunification of Korea, ain’t got nothing on this.

Today is the day you show everybody that “you’re kinda a big deal now”. The day you finally tell your ex “we should definitely catch up for coffee sometime” and never call. The day your flex echoes into eternity and becomes the stuff of legends.

One shot. One opportunity. To seize everything you ever wanted.

So here’s our guide to not letting it slip at your high school reunion.

Pull up into the carpark like a G

Tom Ford Suede Blouson | Photo via. Mr Porter
Style is a way of saying who you are without speaking. In this case, the owner of a small island nation.| Photo via. Mr Porter

If you weren’t terribly fond of high school – the incestuous intergroup dating, the academic competitiveness and teenage puberty in general – the reunion is a perfect time for a big ‘F*ck you’ to all of that.

Just imagine pulling up into the school carpark in your vintage black 1955 Mercedes 190SL Convertible, and stepping out in slow motion wearing a Tom Ford Suede Blouson. Crafted in Italy with tan suede and lined in smooth silk twill, this jacket will surely catch the eye of your former classmates. At ten grand a pop, it’s short change when you’ve got a bourgeoning business empire under your name.


Tom Ford Suede Blouson available at Mr Porter

Make it Rain

The colour of envy | Photo by Shibumi

Let’s face it, your high school reunion is about one thing and one thing only: lying to yourself and your peers about how much you actually make and how happy you are with everything in your life. That’s why this solid stick umbrella made by Mario Talarico has to be the finishing touch to whatever you’re wearing (yes, even if it’s not raining, because this is how stunting works).

This thing is expensive af. The handle took an old Italian guy months of steaming and slow pressure to bend into that perfect curve, and the individual grain pattern of chestnut gives each one a unique patina.

Also look at it this way: if it ain’t pouring, you’re using the umbrella as a cane because of that “hamstring injury you sustained saving 3 children in a broken elevator”. But if it is raining, you can literally let your umbrella do the flexing for you as you take home your high-school crush before she gets wet.

Bruh, you’ll be killing it so hard with this thing, you actually might actually believe you’re happy with how your life turned out.


Mario Talerico Chestnut Umbrella available at Shibumi

Be the cool dad

Brunello Cuccinelli photographed by XXXX
“HAHA. No seriously, Bazza if you spill that drink on my jacket I swear to God…” | Photo via

There’s dad style. Then there’s there’s Italian billionaire philantropist-Brunello Cuccinellisweater-wearing dad style.

Designed in the quasi-medieval hamlet of Solomeo, Italy, and crafted by master artisans, Cuccinelli’s sportswear is arguably the most luxurious in the world (with a price to match).

It’s so good, I think you can justify missing the mortgage repayment just this once. Cuccinelli’s cashmere is sustainably sourced from Mongolia, the fabrics are woven by Umbrian artisans (including a convent of nuns – yes mother-effing nuns!), and the garments are even stress tested by women combing for imperfections like an Asian dad with a school report.

The result? A sweater so expensive your missus will probably kill you.

– Will

Brunello Cuccinelli Sweater available at Brunello Cuccinelli.


Go Sevenfold on your high school vengeance

   Those curves call to me. | Photo via Sevenfold

I’ve always loved a good tie. With its not so subtle phallic imagery, it’s the perfect accessory to elevate your outfit into a real power statement at the reunion.

And sitting at the top of the tie hierarchy is the Atto Vannucci Firenze seven fold by Seven Fold – equal parts indulgence and necessity. Handcrafted in Italy using the best local silk supplies from Como, Seven Fold brings back classic style and flair with a vengeance.

Where everybody else’s ties are going to be three folds with a sewn-in separate inlay to add weight and thickness, your Atto Vannucci 7-fold tie is made from a single piece of cloth carefully folded seven times (hence the name) and then rounded off with hand-rolled edges. It’s a right piece of art as it creates a substantial knot and then drapes oh so gently down the chest.

And in Australia where casual is king, I say break the status quo and start a revolution. Wear a seven fold tie instead. (And use a proper knot please.)


Atto Vannucci Firenze 7-Fold Ties available at Seven FoldTie Your Tie.

Cover photo via. South West Airlines

Stay Informed

Join our newsletter to keep up to date with the best menswear in Australia, and receive exclusive subscriber only content.