Stepping Out with Chelsey Wilson

Words + styling: Gavin Mikey Collins | Photographs: Carl David Jones

As a rule I always style outfits from the feet up. This may come as a surprise to the less fashionably inclined but I assure you there is method to my madness.

The transformative power of a new pair of shoes is a special kind of magic. You find yourself standing up straighter and walking with more confidence. In a new pair of kicks the world is your runway.

“Shoes are the quickest way for women to achieve instant metamorphosis” – Manolo Blahnik

Your shoes set the tone of your outfit. They are the exclamation point at the end of your sartorial sentence. As in “I am chic!” “I am sexy!” or “I don’t take myself too seriously!”

You’ll be pleased to discover that the loving relationship you have with your shoes is reciprocal, as they'll keep you grounded (literally) and keep your feet safe from danger. Think of your shoes as that really over-protective parent who is with you every step of the way.

Kind of how we spent the day following Superbalist 100 finalist and sock-aficionado Chelsey Wilson around for the day as she schooled us on how to put your best foot forward.

Slaying the streets in sneakers

As the owner of Feat. Sock co., a designer sock brand for sock-lovers and dreamers alike, Chelsey’s busy days mean she spends a lot of time of her feet. Sneakers obviously make the most sense then. 

“My mornings are usually spent running around from my desk to my stock room organising deliveries. I then take a walk to the post office to send my babies off to their new homes.”

A fresh pair of Nike sneakers complements Chelsey's casual cool style without compromising on comfort.

Style tip: Wear a fancy sock with your sneakers to take your look from fitness to fabulous.

These boots are made for walkin’

Power dressing undergoes a millennial update with this denim on denim outfit. Gone are the days when businesswomen were defined by a pencil skirt and heels. Chelsey explains how she often walks from her shop to the beachfront cafés for meetings with suppliers or clients. And that boots are made for these walks. 

Style tip: A pair of black ankle boots will pull a look together and add polish to the simplest of outfits, even allowing denim a more sophisticated appeal.

Ready for combat

The business world can often seems like a battlefield, so why not dress the part? Pairing leather ankle boots with a military green dress and bomber jacket sends the message that you are ready to kick ass while taking names. The military look has stormed back onto the runways over the past few seasons with oversized bombers and camo prints leading the charge.

“If I’m not wearing sneakers I’m usually in boots, especially in winter. I love combat boots because they make me feel invincible when I’m walking into meetings.”

Style tip: Don't be afraid to spend a little more on classic, good quality boots that will last longer. Well-worn in boots look and feel better and add authenticity to your wardrobe.

The higher the heels the closer to heaven

My favourite quote from Dame Vivienne Westwood is “high heels were designed to place women’s beauty on a pedestal.” With little convincing Chelsey slipped on a pair of dailyfriday block heels in tan and sashayed up and down the street in her dusty pink ensemble.

“I don’t normally wear heels but these make me feel cute. They're also really comfortable.” If she has to drive into town then Chelsey will usually stay on and meet up with friends in the evening. This chic and versatile outfit is perfect for that as it transitions well from day to night. Lose the shades and throw on a sequinned jacket and you’re ready to sparkle from head to toe.

Style tip: There is nothing less glamorous than a girl struggling to walk in heels, so make sure you have practised your strut before hitting the streets. A chunkier heel is great for stability, comfort and is an instant update to its sister, the stiletto.