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An explosion of fabric sits at my feet. Heavy coats sit in stacked piles that threaten to topple over, and silk cheongsams lie unzipped on the bed. Despite the chaos, organising my 89-year-old grandma’s clothes is a reminder that her life has been as vivid as the clothes that surround me.

She’s moving into a retirement village and I am luckily on the receiving end of her closet clean-out. My grandmother was a sartorially savvy woman and the craftsmanship of the clothes she has collected and worn over the years is unlike anything I’ve seen.

They’re a glimpse into what her life was like as a twentysomething, beyond a blurry figure in a black and white photo. And although her garments are decades old, they still burst with life.

So, how can I incorporate pieces from 1960s Hong Kong into my more contemporary wardrobe in Sydney? Not only can my grandma’s clothes be more physically restrictive, the style can look very different to the clothes we wear today.

I’m no stranger to old clothes – most of my wardrobe is a result of hard-fought battles at the op shop. But, those clothes feel easier to style compared to my family heirlooms. New York-based stylist Chloë Felopulos understands this tension – family heirlooms can feel difficult to make your own because “you’ve seen it worn in such a specific way that you want to preserve that picture of your grandma”.

It can feel like you don’t have permission to wear those pieces, she says, but she reminds me that clothes are made to be worn. “Know that for a lot of people [passing on their garments], they just want their clothing to have another life.”

To give me some advice on how I can wear my grandmother’s clothes in my style, I talked to two style experts who specialise in vintage clothing – Felopulos and Cora Walters, a curator at Cora Violet Auctions.

Play dress-up, and mix patterns

To overcome this mental block, Felopulos recommends I give myself time to experiment. It takes a while to feel comfortable trying new things like an unfamiliar silhouette, colour or pattern. Even more so to figure out what pieces in my wardrobe would work with the heirlooms.

For this floral coat Walters encouraged me to lean into the “romantic vibe” of the coat, for a “real antique Victorian” look. She says I could pair this with bloomer shorts, knee high socks and ballet flats. I don’t have bloomers but I do have a pair of satin shorts. Although this style is outside my comfort zone, I like exploring this more feminine aesthetic.

In a similar vein, I’m inspired by the coat’s 60s design with its cropped length and bell sleeves, and pair it with my gingham capri pants and denim mules. Despite the pattern mixing, I think the way the floral design flows into the print of the pants, helps create a cohesive look.

I wear this to the markets and love the way it makes me feel – being surrounded by old things while wearing a special old thing.

Try ‘colour sandwiching’

Felopulos also recommends colour sandwiching, which involves matching two colours in the outfit together: “If the top is red, you could do a nice grey bottom, and pair it with a little red heel or a red lip,” she says.

For a simple colour combination, I decide on my grandma’s black shirt with my pleated white shorts and trusty black boots.

I like the contrast between the shirt’s slim fit with its upright mandarin collar, and the baggy bottoms. The monochrome colour scheme and the footwear make this outfit feel more contemporary, and I can imagine this slotting very easily into my rotation of go-to outfits.

Unfortunately, the top is too small for me. I can’t do up the last button on the collar, and material bunches up oddly around my shoulders. And after moving my arms too quickly, a seam on the sleeve rips. I don’t want to throw away the top, so I’m thinking about having it altered into something sleeveless.

Set the scene

Older clothes and accessories aren’t always practical for modern living, but this shouldn’t consign them to the back of the wardrobe.

Felopulos’ grandmother’s gold chain mail purse, for example – “can hold maybe a chapstick and a credit card”, but she still wears it, albeit only on occasions where she doesn’t need her full arsenal of products.

With this in mind, I think of my grandmother’s cheongsam: hot-pink, high-collared, form-fitting. To work within these physical constraints, Felopulos recommends envisioning where my grandmother would have worn these clothes, and translating that into my life: “Think ‘what’s my version of my grandma’s night out?’”

I initially write off wearing my purple ballet flats with this cheongsam, thinking two brightly coloured items together would be over the top. But Walters says pairing similar looking fabrics creates a “soft harmony”.

So I wear the shiny duo out to dinner. It’s a test of courage wearing a hot-pink cheongsam at a neighbourhood Italian restaurant. Not only do I feel self-conscious, but I’m annoyed by how the dress restricts the amount I can eat. Maybe my grandma’s diet in the 60s included less pasta and more cigarettes.

I ask Walters how she navigates anxieties around wearing clothes from another era. Instead of shying away from the extravagance of the designs, she embraces them.

“The opulent fabrics, the movement, the beautiful old labels … no one can touch that,” she says. “When I wear a piece like that, people do a double take. It makes you feel singular.”

I was worried that wearing clothes from 1960s Hong Kong would make me look like an extra on a period drama. But then, putting on her silk coats and wearing her jade jewellery, I remember Felopulos’ advice: as long as you’re wearing the piece with pride, you’re wearing it the right way.