Bree Pickering is director of the National Portrait Gallery. Ahead, she shares her style inspiration, including why Sydney in the early 2000s is her favourite fashion era.

I’d describe my style as relaxed, tailored and unpretty – I steer away from the hyper-feminine.

The most recent addition to my wardrobe is a pair of black Maticevski leather pants (pictured below) that are so long they drag on the floor. I’d been lusting over them for some time. The oldest thing in my wardrobe is a digital-print silk T-shirt from Tsubi [now Ksubi] from the early 2000s.

My favourite fashion era was Sydney in the 2000s. So many cool designers popped up that had a lasting impact – Tsubi, Romance Was Born, Zimmermann, Sass & Bide. The fashion had a distinct flavour and I could wear my denim hotpants on any occasion.

On my first date with my husband 20 years ago, we went to an art fundraiser and I wore a Buffy-inspired ball gown. Now, I’d wear my Song for the Mute macramé skirt with a relaxed T-shirt and a heel. For the red carpet, I’d love to wear Romance Was Born.

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On a plane, it’s any combination of Nagnata basics – it’s lovely to have wool on your skin for long-haul flights – with compression socks and my Adidas x Stella McCartney “Ultraboost Leopard” sneakers.

Designers I’m loving include Courtney Zheng and Kourh. Courtney Zheng pulls masculine and feminine together in a beautiful way, and Kourh’s wild denim looks are fun. I love seeing new Australian talent in the visual arts and that extends to fashion.

Three essential items in my wardrobe are a pair of Chloé wedges, which despite being very high are really comfortable, Rolla’s barrel-leg jeans, and tailored pants – I like Camilla and Marc, Scanlan Theodore and Bassike.

I sleep in a silk hair bonnet because I’ve got curly hair; anything else is secondary.

My favourite jewellery is made by my husband, Marley Dawson. He’s an artist and sculptor, and he only makes jewellery for me. There’s a pendant crafted from a vintage billiard ball that looks like a planet – it’s beautiful. It also makes a good fidget toy.

My favourite childhood outfit was dark-denim pedal pushers with a mint-green halter top and red-and-white platform wedges, like the ones the Spice Girls wore. But the coolest thing I ever owned was a pair of Reebok high tops my aunt brought from the US. I remember what it felt like to have something nobody else had.

On my wish list is a pair of knee-high Margiela boots I regret not buying in 2015 – they were so good. I’ve thought about them every winter since, and I’m still searching for them. The shoes I wear most often are Christopher Esber crystal mesh “Minette” flats, and various Camilla and Marc “Rhys” pumps, including a white fluffy pair and burgundy pony pair.

I make fashion mistakes all the time but if you don’t try something you don’t make mistakes, and it’s way more fun to try. I’m up for anything; I love the performance and fun of fashion.

My fashion icons are my fellow judges on Portrait Artist of the Year. Robert Wellington is a connoisseur, a collector, who only wears Vivienne Westwood. Abdul Abdullah always looks cool, and it’s always about art. They’re at opposite ends of the fashion spectrum but fully themselves and I find that inspiring.

On a typical working day, I usually wear black tailored pants with an Alémais shirt – something I can level up with accessories. I live in Canberra, so on the weekend you’ll find me in a Dion Lee cropped puffer jacket, matching puffer pants and Nike “Huarache” sneakers.

Bree Pickering is a judge on Portrait Artist of the Year on ABC-TV and iview.