A week of winter dressing with fashion writer Amberley Colby

An ode to the staple layering pieces.

Before I moved to Sydney from Aotearoa, people would often tell me the city only really has two seasons: summer and winter. I didn’t quite appreciate what they meant at the time, but now, as I settle into my second winter here, I do. 

One day in late May or early June, the temperature hovers around 24 degrees, then seemingly overnight, the daytime high drops to 16. There’s no going back.

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As someone who dresses more by instinct than forecast, the sudden shift has caught me a little off guard. After months of dressing for the lingering warmth, I’ve been unsure what to reach for or how to dress for days that begin brisk, warm up by lunchtime, and cool again after sunset.

As a result, I’ve found myself relying on the simplest foundations in my wardrobe: a well-cut pair of jeans and a cotton long-sleeve top. They’re the kind of pieces that offer warmth without feeling heavy, creating an easy base that can be layered up or pared back depending on my mood.

This change of season has also had me returning to a brand that feels especially familiar. Growing up in New Zealand – the birthplace of Glassons, for those who don’t know – the brand’s staples were always at the top of my wishlist. Back then, the changing rooms were famous for their plush velvet carpet and pink chandelier ceilings, and simply trying things on felt impossibly grown-up. As a tween, I wanted nothing more than to finally fit into its clothes. I still remember my first purchase: a very Y2K graphic tee that was several sizes too big for me. I wore it anyway and absolutely treasured it.

A lot has changed since then. Glassons has evolved alongside my own wardrobe, but it’s still known for what it has always done well: elevated everyday essentials. This winter, its new arrivals are the kind of items I’ve been reaching for most: flattering denim and easy layering separates.

Armed with seven pieces from the new winter season in my wardrobe, I challenged myself to style four outfits over a winter week in Sydney. Here’s how it went.

’90s minimalism

‘Jeans and a nice top’ is a beloved formula for a reason. On one of the week’s milder days, I was heading out to run a few errands before settling in for an afternoon of writing, so I wanted something that looked polished while still being comfortable. I landed on these low-rise jeans in a light blue wash, paired with a classic three-quarter sleeve boat-neck top. “

You look a bit like Carolyn Bessette,” my partner remarked, upon first seeing me. I had nailed the vision. In honour of the minimalist muse herself, I kept the rest of the look simple with black ballet flats, a leather belt, oversized sunnies and my ever-reliable hobo bag. 

Coffee date

In my humble opinion, nothing spices up an otherwise monochrome outfit like a pop of red, which was exactly my strategy with this look. With a coffee and lunch date with my partner on the agenda, I reached for Glassons’ organic cotton black long-sleeve and paired it with white wide-leg jeans, rolled once at the hem.

To add a little texture and dimension, I added a knit long sleeve around the waist, then finished the look with a baguette bag and red thongs – because in Australia, we don’t let winter stop us from showing our toes.

Off to the shops

I love playing with proportions, and these ultra-baggy jeans felt like the perfect place to start. Designed to sit low on the hips, they’re a fresh take on the classic barrel leg. As a tall girl, I especially appreciate the extra length, which creates that puddled effect around the ankle I love so dearly.

For an afternoon of homeware shopping, I paired them with this impossibly soft faux suede jacket (brown is the new black), along with my trusty Tabis and, yes, another baguette bag. I loved the combination of these two voluminous silhouettes.  

Sunday Vino

In an effort to stave off the Sunday scaries, my partner and I have developed an unofficial ritual: heading to a neighbourhood bar for a glass of wine on Sunday afternoons. It’s become our favourite way to ease into the week ahead, and the light drizzle that afternoon only made the prospect of settling in somewhere cosy even more appealing.

Having developed a real liking for Glassons’ baggy low-rise jeans, I reached for them again, pairing them with a knitted boat-neck top, beaded heels, a matching bag and a fine gold necklace. Equal parts comfortable and considered, it was the perfect outfit to while away a few hours over glasses of orange wine – the ideal antidote to the Sunday scaries.

To browse the Glassons collection, head here.