Confirmed: This Sydney Girl Has the Best Street Style

Recently, we held our second annual Who What Wear Australia Street Style Awards (aka #TheStreeties), which celebrates the tastemakers and industry insiders whose style sets the tone and influences the world of fashion today. As we look back at Fashion Week Australia (remember the stunning accessories and the show-stopping outfit details?), it's incredible to see that it delivered plenty of honourees, but there was one in particular who truly deserved the crown… Chloe Hill—who was awarded the coveted Street Style Star of the Year Award. 



Dave Wheeler

On Hill: Christopher Esber Leather Jacket (coming soon), Life With Bird Trench (coming soon), H&M T-Shirt (shop similar style), Bianca Spender Rust Velvet Viceroy Pant ($495), Beau Coops x Romance Was Born Jasmin Mule  Heel ($332), Tiffany & Co. HardWear Wrap Bracelet ($1600), Tiffany & Co. HardWear Ball Pendant ($370).

Chloe Hill is exactly as you would imagine—charming, colourful (have you seen her social feed?), and quite possibly one of the most respected fashion girls in the industry. As the winner of our 2017 Street Style Awards, we put the creator of Cool Pretty Cool in front of the camera, and dressed her in our favourite Australian designers—then added select pieces from the new Tiffany & Co. HardWear collection to complement her style.

With jet-lag setting in after a long-haul flight back to Australia (Hill has been working in Europe for the past six months), she arrived at our warehouse location in Sydney with warmth and grace. We sat down and discussed her love of vintage fashion, plus her successful career transition from a fashion magazine market editor to launching her own digital brand.

Keep scrolling to read the exclusive interview with our Street Style Star of the Year.



On Hill: Bianca Spender Forest Mist Silk Bloomsbury Dress ($925), Tiffany & Co. HardWear Graduated Link Necklace ($2500), Tiffany & Co. HardWear Wrap Bracelet (worn as necklace) ($1600), Tiffany & Co. HardWear Link Bracelet ($1800).

Who What Wear Australia: Chloe—it's safe to say that you are a creative spirit at heart. What attracted you to a career in fashion and how did you start out?

Chloe Hill: I grew up in New Zealand and I didn’t know a career in the fashion industry was possible—I never had anything like that around me. When I moved to Sydney, I saw a course at FBI to do fashion in business and on the first day, I got placed in an internship with Cleo magazine. It all happened very naturally and I never had in mind that I was going to work in magazines. I worked my way up slowly and obviously you really have to love working in magazines or styling. It’s so much hard work but I was very lucky to stumble into a job that I loved so much.

WWW: How did you transition from an editor role to becoming a sensation in the bloggersphere?

CH: I always had a blog on the side and always worked on different freelance projects. Even though it was a big deal leaving a magazine (because I always had been with one), I already had bits established on the side. It was scary going out on my own but it opened up opportunities and gave me the chance to explore other roles. It meant I could launch my own site–Cool Pretty Cool.

WWW: You’re Instagram handle is @chloechill. Would you describe yourself as a chilled person?

CH: Not at all! I mean, I feel I am more chill now but when I first started in the industry I definitely wasn’t. Chill is my nickname because it was my first work email address. 



Dave Wheeler

On Hill: Christopher Esber Jacket and Pants (coming soon), Senso Zaren II Shoes ($249), Tiffany & Co. HardWear Ball Ring in 18k Rose Gold ($1900), Tiffany & Co. HardWear Ball Ring in 18k Gold ($1900), Tiffany & Co. HardWear Triple Drop Earrings (shop similar style), Tiffany & Co. HardWear Ball Bypass Bracelet ($2800). 

WWW: How would you describe your style?

CH: It’s crazy. Actually really crazy! I like really random pieces and I don’t like anything too plain—I want everything I wear to be special and make me happy. It’s probably quite feminine, and very eclectic.

WWW: Looking at your Instagram, your social feed is so colourful and your look is bold. What influences you?

CH: I used to wear a lot of black and dressed a lot more simple when I first started in the industry. In my early 20s, I was still finding my style and you learn a lot working with stylists. I became more confident and had time to figure out what I loved and what suited me. I had lots of outfits that were total duds, but it was about trialling different bits and pieces. That’s what fashion is about—you gotta play around to find out what makes you happy and puts you in a good mood.

WWW: What’s your number one fashion item that puts you in a good mood?

CH: It's usually a bright pop of colour and I also love a really good pair of shoes which can change your day. Maybe a colourful pair of heels or even an eclectic coat. 


On Hill: Romance Was Born Crimson Magnolia Gown ($1650), Tiffany & Co. HardWear Ball Hook Earrings in 18k Rose Gold ($1400), Tiffany & Co. HardWear Link Bracelet in 18k Gold ($4550), Tiffany & Co. HardWear Link Bracelet in 18k Rose Gold ($4550), Tiffany & Co. HardWear Ball Ring in 18k Rose Gold ($1900), Tiffany & Co. HardWear Ball Ring in 18k Gold ($1900)

WWW: Do you feel your style has evolved a lot over the last five years?

CH: Yes, I think so. A few years ago, I was still buying pieces that weren't quite me. I love shopping sales so sometimes I would compromise picking a piece that wouldn’t suit just to find a bargain. So now, I've started being more picky and I will only buy a piece that is special—it’s important that if I do buy something, I am going to wear it more than once. I shop a lot of vintage but also special pieces from Australian designers and international labels.

WWW: Where do you go for a hit of vintage fashion?

CH: I love it! It’s got a huge selection. But I also love flea markets, too, especially since I’ve been travelling. Every town I go to, I’ll research vintage stores and markets and spend hours trawling through them. It takes effort, especially because I am tall and have big feet.

WWW: If you’re ever in a creative slump, how do you find inspiration?

CH: I normally switch off from everything fashion related and have a good sleep. The worst killer of creativity is being exhausted and getting run to the ground. Having the time to re-energise is needed, and also visiting inspiring places. Japan is really inspiring for me—it’s vibrant and there’s so much happening. Plus they have lots of vintage!


On Hill: Don't Ask Amanda Clara Faux Fur Coat Cream ($159), Bianca Spender Blush Velvet Wonderland Gown ($955), Tiffany & Co. HardWear Graduated Link Necklace in 18k Gold ($15,700), Tiffany & Co. HardWear Ball Ring in 18k Rose Gold ($1900), Tiffany & Co. HardWear Ball Ring in 18k Gold ($1900).

WWW: What do you think of street style here in Australia?

CH: Australian style doesn’t have the in-built culture that it does in Europe, so that’s why trial and error is so important. Australians are great at adapting to trends, and that minimalist aesthetic is so strongly influenced by Australians. 

WWW: What do you think of Australian street style?

CH: Australians take risks—they try colour and they push the boundaries. Even if it’s just to take a photo, I think it’s great because they can show the rest of the world that they can have fun!

WWW: What were you most excited about at Fashion Week Australia?

CH: The Romance Was Born fashion show! Every year it’s the thing I look forward to the most. There are always such fun beautiful looks, and you can expect something different every year. They’ve collaborated with Del Kathryn Barton—there’s a lot of power in collaboration.


On Hill: Topshop coat (coming soon), IRO Altara Dress ($406), Tiffany & Co. HardWear Graduated Link Necklace ($2500), Tiffany & Co. HardWear Ball Pendant ($370), Tiffany & Co. HardWear Ball Hook Earrings ($415)

WWW: On your Instagram, is there a look that you are still head over heels for?

CH: There’s a pair of pink cat-eye sunglasses that I shopped for when I was in London and I changed all my profile pics to ones of me in these glasses. I did a shoot a couple of days ago with a model, and she was so in love with them that I gave them to her. It was the most heart-wrenching thing ever—they were my favourite. 

WWW: On social media, have you found a piece that you've fallen in love with and want to buy right now?

CH: Yes—Poppy Lissiman has fun accessories and there was a post of sunglasses with tortoiseshells and stars on them. I’ll be keeping my eye on them when they drop.

WWW: What’s your tip to capture the perfect fashion Instagram shot?

CH: I feel my Instagram shots aren’t [perfect]—I feel if it’s too perfect, people don’t like it because they know its not me. It’s going be different for other people but the number one rule is be true to yourself and don’t force it.




Dave Wheeler

On Hill: Sass & Bide Heat Rising Capelet ($595), Pereira Fitzgerald Shearling Pullover ($2200) and Ruffle Dress ($420), Tiffany & Co. HardWear Ball Pendant Necklace ($370), Tiffany & Co. HardWear Wrap Bracelet ($1600). 

Model: Chloe Hill
Photographer: Dave Wheeler
Hair and Makeup: Jasmin Lo
Styling: Amanda Stavropoulos

What's your favourite look from our shoot? We'd love to know! Share in the comments below.

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