In Conversation: Observe

It’s a family affair for Massimo and Alessia Acquaro, the sibling duo behind local label Observe. 

The young Melbourne brand started off by perfecting the basics before taking their talents to more ambitious executions of the entire wardrobe from tailored trousers to a newfound passion for outerwear. They discuss what they’ve learnt so far “Watching The World Go By”.

Italian families are often known for strong traditions. Growing up, was fashion always on the table, or was something a little more “safe” expected?
Growing up in an Italian family, tradition is central, and with it, an expectation (sometimes spoken, sometimes implied) to pursue something stable and secure. Fashion was never discouraged, but it also wasn’t the obvious path.

Looking back, it almost feels inevitable. Both sides of our family include talented tailors and seamstresses, so creativity and making were always part of our environment. 

Our parents’ generation grew up with a clear mandate: study, secure a job, and build financial security as quickly as possible. Both our mum and dad have been successful in their careers through hard work and genuine passion, and that mindset shaped how we were raised. 

At the same time, creativity has always run through our family. We’re surrounded by relatives who followed their interests and built their own businesses. That quiet legacy of independence normalised the idea that you don’t have to follow a conventional structure to build a meaningful life. Our grandparents, parents and extended family have all been inspirational, with different talents, but all fiercely creative and independent. 

MA: Like a lot of kids, I initially gravitated towards “safe” aspirations—law, maybe finance—before discovering design through school and later architecture. Architecture felt like a way to balance creativity with structure. That foundation gave us confidence. Having degrees and a clear fallback meant we could take creative risks without feeling reckless. 

In many ways, what we’re doing now reflects our generation’s desire to step outside the 9–5 (and into the 9–12) while still taking responsibility for our choices. Our parents may not have taken this path themselves, but they trust our vision and that trust has mattered a lot.

AA: I started out studying nursing, but quickly realised my creative side needed an outlet. I shifted into Communications and Advertising, which ended up being the perfect fit. It’s allowed me to combine my studies and professional skills with building and developing our brand. 

If Observe disappeared tomorrow, what job would the other sibling succeed at?
MA: Alessia would make a great film producer. She’s brilliant at organising creative chaos, getting people aligned and making sure things happen on time. It’s basically what she already does, just with a bigger crew and higher stakes. She has a strong visual instinct and understands what it takes to actually execute a concept, which could also land her a role as a creative or art director too. She’s also a real people person and knows how to bring out the best in everyone.

AA: Massimo would thrive in architecture or as an art director. He’s disciplined, solutions-driven and works straight through problems rather than around them, which is essential in creative work, where things rarely go to plan. He has a sharp eye for detail and a strong ability to reframe challenges as opportunities. Buildings, façades, structure, colour and form genuinely excite him. It’s… a bit strange, but very useful. 

When you’re designing, who are you actually picturing wearing the clothes?
Everything we make is something we want to wear ourselves, in that moment in time, what feels right, considered and genuinely cool to us. If it doesn’t work on our own bodies or in our own lives, it doesn’t make it into the collection.

A huge source of inspiration comes from what surrounds us, our friends, our travels, and our family. It’s about paying attention to everyday context and lived experience. That act of observation is really at the heart of how we design.

What’s one thing only a sibling could get away with saying in a work meeting?
Honestly, when you work with your sibling, “work meetings” don’t really exist. Work and home life blur constantly, we’re always talking about Observe.

Sometimes messaging each other from across the room is more efficient than sitting at the same table and risking an argument. The upside is that total honesty is built in. If something isn’t working, we say it straight away. If something lands, we both know instantly. It’s slightly terrifying how well we can read what the other is thinking.

Who takes longer to get dressed? (We’re thinking it’s you, Mas.)
Please don’t undermine my ability to look effortlessly cool.
No further comment. Thank you.

What’s one thing Observe will never do—or be?
We never want Observe to feel like a “business”. That might sound counter-intuitive when you’re running a label, but our passion is design not chasing trends or sales cycles.

Our goal is for Observe to feel timeless, understated, and never try to say too much.

What’s more intense: running a brand together, or an extended family lunch?
We can’t be sure who in the family will read this, so we’ll answer carefully.

Everything in an Italian family is loud and chaotic, but it’s also driven by genuine passion. Whether it’s day-to-day operations at Observe or a long family lunch, the intensity is always there. 

What’s the hero piece from your latest collection?
We’ve really grown to love designing outerwear, and the Vented Jacket is probably our favourite piece from the Spring/Summer 26 collection.

A lot of structural detail referenced from the archives of some of our favourite brands went into making it feel truly finished. Although, honestly, nothing ever really is.

The latest collection from Observe is available now at UP THERE.

SHOP THE COLLECTION