Hill, a New Zealand-born stylist, is hard to scroll past once you happen upon her playful use of colors, obvious love of prints, and seemingly DGAF attitude toward the old take-one-accessory-off-before-leaving-the-house rule. A former editor at InStyle and Oyster magazines in Australia, Hill switched gears in 2016 to launch Cool Pretty Cool, a digital publication to explore and celebrate style and the fresh faces behind it.
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While Cool Pretty Cool itself serves as a source of style inspiration—and often through a global lens, thanks to Hill’s demanding work travel schedule—it’s her personal Instagram we’re so often returning to for fresh outfit ideas. Piled-on accessories, daytime sequins, and impactful prints layered on in multiples, it’s these unexpected choices that have us wondering why we haven’t been following her joyful take on dressing all along.
Below, Cool Pretty Cool’s founder explains more about not worrying what others think, not following the most viral trends, and which basics are currently in heavy rotation in her very non-basic wardrobe.
From the outside, it’s obvious your style is bold, colorful, and lots of fun. How do you describe your own sense of style? How has it changed over time?
“When I started in the industry as an intern, I tried to wear things I thought people would think looked ‘cool.’ I didn’t wear so much color and often bought into trends I didn’t personally love in an attempt to fit in. As I got older and felt more comfortable, I started experimenting. I started wearing pieces that made me happy and started caring less about what others thought. I do think it’s also part of growing up and discovering who you are as a person, but I do encourage young people to be less afraid of impressing others!”
What are your earliest memories of fashion and expressing personal style?
“I grew up in a big family (I’m the oldest of six), and my mum was very thrifty with dressing us. She would sew a lot of my clothes and was amazing at utilizing hand-me-downs and thrift store finds. She taught me a lot about creativity from a young age, and that’s stuck with me ever since.”
What advice would you give to someone who wants to embrace a bolder look but is still pretty afraid others may judge or not approve?
“It’s all about confidence. If you tell yourself you can and you love what you are wearing, anything is possible. Also, the more you experiment, the more comfortable you’ll be with trying out wild colors and combinations. People are going to stare—that’s a natural instinct when someone walks by in a bold outfit. It doesn’t mean they hate it! And if they do, so what?”
Who are some of your biggest sources of inspiration when it comes to personal style?
“There are some really key people in the industry who have always inspired me. Anna from Romance Was Born is the most stylish woman I know. Of course, Iris Apfel has forever been an icon for me too. And I find inspiration in people on the street. Last week I saw an elderly couple in Hong Kong in printed shirts and bum bags—moments like that stick with me.”
Would you call yourself fearless when it comes to fashion? Are there any trends you’d never wear?
“I still have days when I put on a crazy outfit and decide to swap to something plainer. I always want to feel comfortable in what I wear, so some days that means I’m not in the mood for such an over-the-top look. But there are so many trends I would probably never wear, pretty much anything that has gone really mainstream turns me off. Like those midi leopard skirts everyone has been wearing—they look cute, but if every second girl is wearing it, you won’t see me dead in it.”
In that case, what are the most loved, most worn items in your own closet?
“I only acquired my Prada embellished cardigan recently, but it’s without a doubt the best thing I’ve ever owned; I wear it every few days and people stop me on the street all the time to talk to me about it! Because I travel so much, I would have to say my Holiday The Label hoodie is also in the top three, although my husband recently realized how cozy it is, so we have to fight over it now! Lastly would be my Levi’s ribcage jeans. When you find the perfect pair of jeans, you should never let go.”
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What’s an outfit formula you return to time and time again?
“A midi skirt and sweater combo. It’s the kind of outfit I can feel good in but also not have to think about. It’s flattering, there are no moving parts, annoying straps or short hems to pull down.”
Being from New Zealand but also having to travel tons for work, are there any trips you’ve taken that have changed your outlook on fashion?
“I spent a bit of time in Japan last month and I was so inspired by people on the street there—they really celebrate individualism and everything they wear is so thought out. They made me feel like I need to experiment more with accessories and styling tricks, and boy to they know how to work a silk scarf!”