Executive Style: From CEOs To Entrepreneurs - How Five Fashionable Leaders Dress For Work

A new season offers a fresh perspective for professional dressing from those at the top.

With spring deliveries making their way into stores, it’s perfect timing for the second instalment of our style series, where we discuss with various leaders from all backgrounds how they get dressed to get the job done.

At a time when New Zealand’s unemployment rate has reached its highest level in three years, it’s vital to consider the power of dressing for the role you want; or in the case of these four leaders, using a professional wardrobe as a tool to communicate their values and expectations in the workplace clearly.

In this spring edition, we welcome Kirsten Lacy, the director of Auckland Art Gallery Toi o Tāmaki; Kirk Hope, outgoing CEO of BusinessNZ and new CEO for Financial Services Council of New Zealand; Jaimee Lupton, the beauty entrepreneur and founder of Monday Haircare and Osāna Naturals; and Rob Harvey, CEO of global marketing and advertising agency Dentsu.

In their respective roles, each leader offers their unique perspectives on the clothes they rely on to lead with clarity and conviction.

From wardrobe staples that help reinforce a sense of mana in the workplace to treasured adornments that inspire a sense of identity, these five faces offer up their unique and individual perspectives on how they use clothing as a tool for success.

Kirk Hope, outgoing CEO of BusinessNZ and new CEO for Financial Services Council of New Zealand

A sharply tailored look with a sense of sophistication, Kirk’s working wardrobe has helped shape an extensive career as one of Aotearoa’s leading CEO figures, announcing in June his resignation as CEO of BusinessNZ after nine years. He steps into the role of CEO of Financial Services (FSC) of New Zealand on September 18. Prior to joining BusinessNZ, Kirk was CEO of the New Zealand Bankers’ Association, Executive Director of the Financial Services Federation and held a range of senior positions at Westpac, including Head of Government Relations and Regulatory Affairs.

How would you describe your approach to getting dressed for work?

Professional, classic, comfortable, versatile. When days are long (12-15 hours) your work dress needs to be professional for the circumstances (usually a suit) - and that may vary during the day from meetings with public sector officials, parliamentarians, or other stakeholders, to media interviews, to member and stakeholder hosting.

Sometimes those meetings will be long and you need to be focussed so the clothing needs to be crisp, but comfortable. I tend to favour a navy suit - sometimes patterned, with a white shirt and black belt and shoes. Sometimes a tie. I also keep shoe polish in my desk drawer because a bit of polish can really make a difference to keeping a good pair of shoes looking good.

Do you remember what you wore to your first job interview?

I went and spent about $250 bucks in 1989 and bought a light grey flecked blazer, dark blue striped tie, black trousers and black loafers. I remember fighting against my desire to buy a Don Johnson-esque pastel outfit. I was 17 and interviewing for a job at a law firm. I got the job!

What is one key wardrobe item that you rely on to feel pulled together or an item that is a trusted reliable piece?

Navy suit. It means business time. Or a light blue Canali tie that a mate gave me - high quality, classic and versatile. I carry it in my work bag (an awesome gift from the team at BusinessNZ) just in case.

In your current role, you are dealing with so many different types of people, personalities and departments. How does your professional attire help convey a sense of clarity to the people around you?

When it comes to looking sharp and professional in the workplace, what elements do you allow for a sense of creativity or self-expression when it comes to getting dressed for work?

Clothes that are good quality and fit well, and simple, classic accessories like pocket squares, ties, quality shoes and a good watch.

What was the last item of clothing, accessory or adornment you bought to wear for work?

A hand-wound gold Longines tank watch with a black leather strap. It’s very classic and vintage, and was not expensive at all.

New Zealand businesses and fashion brands are experiencing some challenging times - what local businesses or brands do you enjoy shopping at for quality workwear?

Crane Brothers, Working Style, Rembrandt and World – outstanding New Zealand businesses that continue to provide excellent quality clothing with a broad range of options.

Kirsten Lacy, director of Auckland Art Gallery Toi o Tāmaki

Joining the gallery as director in 2019, Kirsten has also been vice-president and committee member for the Public Galleries Association of Victoria. Her background as an artist also allows her to implement a sense of creativity into her professional wardrobe. With master’s degrees in Art History and Curatorship, as well as Business Administration, Kirsten has an in-depth understanding of the discourse of art theory and museology and a track record in brand development, financial management and organisational performance.

How would you describe your approach to getting dressed for work?

For a woman in an executive role, there is a lot at play. The extent to which you express femininity, cultural nuance, personality, your role and, importantly, how much walking is ahead in your day, are all considerations. It would be easiest to find a corporate uniform for work and stick to variations of it day after day, but I’m way too mood-driven for that.

If I’m feeling good I tend to make more adventurous colour choices. If I’m feeling the need to self-nurture I go for something muted and under the radar. If I need a pick-me-up, it’s playful stockings, crazy sunnies, or favourite heels that can provide the lift needed. What I’ve learned is you can absolutely break the corporate uniform rules – you just have to know when you are and balance it overall.

I also take into account that a woman’s body is often more evident than a man’s and finding clothes that fit, feel comfortable, are feminine and express who I am is actually quite a task every day of the week. So some days putting on overalls, working from home and dressing from the neck up for meetings is a very productive, happy reprieve.

Do you remember what you wore to your first job interview?

Long, A-line denim skirt, ankle lace-up boots and a black, waisted suit jacket with pink satin lining and puff sleeves. That was 30 years ago and I’m still struggling to rid my wardrobe of the puff sleeve! It’s a cringe-worthy, nostalgic anchoring – not dissimilar to the rounded collar shirt or embroidered lapel.

These features keep pervading my choices and likely derive from when I was a teenager, abandoned Christianity, discovered feminism and leaned into a youthful yearning to express a subversive intellectualism in the hope that my seriousness might be recognised but also entirely deluded by playfulness.

What is one key wardrobe item that you rely on to feel pulled together or an item that is a trusted reliable piece?

A good suit jacket transforms just about anything into a just-in-time and ready-for-work look. The kookier the pairing, the more it speaks to a full, active life and readiness to get into the mahi. Pantaloons and runners, long boots and miniskirt or a summer maxi and sandals – throw a long-line suit jacket on, roll your sleeves up and you are good to go.

In your current role, you are dealing with so many different types of people, personalities and departments. How does your professional attire help convey a sense of clarity to the people around you?

We have a lot of evening events at the gallery, and I cannot have enough dresses, dangly earrings or heels as the circulation of events is so high and I am often giving speeches and need to project vibrancy and feel confident.

In the day-to-day, I usually look ahead at my schedule when deciding what to wear. If I have a lot of internal staff meetings, I want to express optimism, pride and a down-to-earth work ethic. If I’m meeting with external partners, I summon up more formal or statement looks and I could definitely use some fashion assistance here.

Where do the worlds of fashion and art intersect for you on a personal level?

I hope to never grow out of dress-ups. For me, fashion is the gateway to play, and play is personal. If you think about it, to be playful and express ourselves we need to feel secure, happy and without significant stress. Dressing up to me is a signal of feeling safe and loved. It’s a sign of self-fulfilment, embodiment and joy. The creative mind is no different. It is very difficult to be creative if you are besieged by fear of making a mistake or not being accepted. Creating safe spaces where people are free to express themselves and to play helps us explore identity, signal values, show our intentions and interrelate with others.

Fashion and art have long interplayed as disciplines and regularly swap places. The exhibition Modern Women: Flight of Time now showing is case in point. The portraits of women are very much centred on their active gaze and the pose of the sitter, but importantly the paintings also showcase the women’s dress and fabric design. The artists and sitters are making a statement about how modern women of the time deliberately chose clothing for their own pleasure and enjoyment, not to help hook a husband or satisfy the male gaze.

The paintings have inspired a new range of silk scarfs by Karen Walker, who is paying homage to the artists and their paintings, but also adorning women today with her creations.

Artists value self expression and identity. How does self expression and an understanding of your own personal identity manifest itself in the way you dress for work?

While I love dress-ups, dress-ups at work is another thing. Every year at the Kaimahi Christmas gathering it’s a particular kind of challenge which is equally terrifying and hilarious. While the executive in me knows it is way too personal to share my penchant for facial jewellery or lashings of chest pearls, it is also a competition replete with judging and prizes! So I find myself in a real bind: maintain one’s reputation or forge a new one?

For last year’s Met Gala theme, I couldn’t resist the pull to the dance floor and decided disco gala was for me. I created a royal blue sequin jumpsuit with mega balloon sleeves and golden peacock adornment (very poorly stitched by hand). It definitely brought smiles to a few faces on the walk home. Ooh and the pearls even found a willing recipient for the event.

How would you describe the gallery’s dress-code expectation from staff? Has it changed or evolved much from when you first came on board?

I don’t think it goes much further than sensible shoes and stain-free, but being a gallery, our people love to express the very best of themselves and we have some exceptional vintage shoppers and seamstresses on staff. I hope staff can create wardrobes for work that are much the same as what they want to wear when they aren’t working. Achieving wardrobe alignment between free time and work time can really help the pocket, and a personal aspiration I try to get closer to each year.

What was the last item of clothing, accessory or adornment you bought to wear for work?

I bought a pendant made from the original 1887 Wales slate tiles from the roof of the gallery. I wanted the team working on the project to know how much I valued their work and wearing a piece of the roof around my neck is a powerful way that fashion can help do that.

Alex Sands and his carvers were commissioned by the gallery’s gift shop in a collab to repurpose the tiles and celebrate the Kia Whakahou Kia Whakaora Heritage Restoration Project, which is due for completion at the end of 2025. The slate jewellery is flying out the door – it’s stunning.

Have there been people in your life past and present who inspire the way you dress?

Yes! I am really inspired by everyday people on the street, particularly older people who prioritise the way they dress and style themselves and don’t give in to mediocrity. I just love it so much when people make an effort to express themselves and share their style with the world. I find it generous, inviting and community-minded to add colour and energy to the street.

As I age I don’t want to become invisible – but the opposite. We need a full community with older people who have seen more of life feeling free to express themselves without need for approval or permission. I follow a couple of photographers on social media who intercept people going about their day and interview them about what they are wearing and their lives. It’s always inspiring to hear these stories and helps me think about how I want to present myself to the world as I age. Letting my hair go fully grey this last year has been the best step toward self-approval, and I think it gives permission to talk about how ageing and style can be the best of friends.

Robert Harvey, CEO of Dentsu

Since taking the helm at Dentsu in Aotearoa in 2013, Rob has helped increase revenue and won the business significant new clients. With nearly 20 years of experience across media and creative businesses, Rob has worked on some of New Zealand’s most iconic brands and campaigns, been awarded in local and international awards shows, and led agencies including Zenith and Publicis Mojo. Rob currently sits on the Commercial Communications Council Executive Board as president, and is on the Media Committee, and Beacons Sub Committee. In a contemporary, fast-paced industry, a clean-cut but modern approach to dressing is what Rob prefers.

How would you describe your approach to getting dressed for work?

I think the way I approach getting dressed for work is reflected in my style. I keep it relaxed and minimalist, and for the most part the decision is what shade and shape of black (I’m not joking). I typically start with what I have on my schedule for that day, and that determines whether I dress more casually or more formally. I will normally start with what I wear on top – do I need a collar or a blazer, then decide on the fit and style of pants, and then my shoes from there.

Do you remember what you wore to your first job interview?

Not exactly. Fair to say I don’t think I had quite discovered my style back then, but I would have worn something I thought conveyed my professionalism without really thinking about whether it was authentic to who I was. I got the job though, so can’t have been all bad. People have often said dress for the job you want, which I think has an element of truth, but I think it’s more important to dress to be true to who you are while obviously being appropriate for the context.

What is one key wardrobe item that you rely on to feel pulled together or an item that is a trusted reliable piece?

Always a black blazer. I have a number of different cuts, but think there is a timeless elegance to a blazer and you can make it work for both casual and formal occasions, pair it with jeans or pants, and t-shirts or shirts.

You also can’t go past a great quality black or white T-shirt. Trust me when I say that over the years I have tried more than most, and you really can’t beat the Uniqlo U T-Shirt by Christophe Lemaire. There’s a reason it’s their best-selling T-shirt around the world.

In your current role, you are dealing with so many different types of people, personalities and departments. How does your professional attire help convey a sense of clarity to the people around you?

The thing I value more than anything is authenticity, and my style is all about authenticity and simplicity. I’m not trying to present myself as anything I’m not, and there is a real consistency as to how I show up. For me there is strength, clarity, and timelessness that comes from black and it has become a part of how I express my identity.

What is a sentimental wardrobe item you have that you can’t part with?

I don’t have great sentimentality for clothing, instead preferring to keep my wardrobe refreshed as trends change around fit and cut.

If I was to reframe that question however, to what is one item I can’t be without, it would have to be my Oura ring (not forgetting my wedding ring of course). Oura is a smart ring that measures physiological biomarkers, tracks your exercise and sleep, and guides your rest and recovery. It’s an awesome piece of tech and has become a key part of how I track my well-being on a daily basis.

When it comes to looking sharp and professional in the workplace, what elements do you allow for a sense of creativity or self-expression when it comes to getting dressed for work?

I normally keep my style simple and monochromatic, but express myself through shoes. This is probably where I spend the most money on my wardrobe. I learnt early that people will often judge your style on your shoes, and whether it’s a beautiful pair of boots or some crisp sneakers I think shoes are where you can show a bit of personality.

What was the last item of clothing, accessory or adornment you bought to wear for work?

I recently got a new pair of Jil Sander sneakers which I love. It’s a fine line with wearing sneakers to work so I probably put too much thought into whether they were right or not, but I think as long as they are crisp and clean then you are probably safe.

Have there been people in your life past and present who inspire the way you dress?

My wife inspires the way I dress. She has an elegant and sophisticated sense of style, with just enough of an edge. She not only inspires the way I dress, but I trust her opinion implicitly and she is always my go-to when it comes to making decisions about clothing purchases.

Jaimee Lupton, co-founder of Monday Haircare, Osana Naturals and Chalon

The beauty mogul combines her love of fashion and beauty into a wardrobe reflective of her day-to-day role as a business owner and entrepreneur working with a range of clients including mass retailer Walmart in the US. With a sharp eye for contemporary womenswear, she melds both high-street purchases with luxury into her daily working wardrobe. As someone who also considers herself as “time poor”, Jaimee prefers the options that online shopping presents to help shape her working wardrobe.

How would you describe your approach to getting dressed for work?

I like to keep it simple and classic: I wear a lot of pants and denim, knits and blazers. I like to prioritise practicality and efficiency, especially as a new mum who is balancing lots of commitments.

Do you remember what you wore to your first job interview?

It wasn’t my very first, but I distinctly recall when going for my job in Sydney with luxury PR agency Black Communications an all-black Zara look!

What is one key wardrobe item that you rely on to feel pulled together or an item that is a trusted reliable piece?

Maggie Marilyn blazer. The new tailoring line is perfect and it’s such a versatile piece. I adore Maggie, we became mums the same month so there is a lot of connection in that! I’m also a fan of anything Harris Tapper – I have so many of their pieces and am more often than not buying the whole outfit from their lookbook.

In your current role, you are dealing with so many different types of people, personalities and departments. How does your professional attire help convey a sense of clarity to the people around you?

I would say I dress for the company I’m keeping, so when I’m in the office with my team my style is quite relaxed, compared to when I’m taking external meetings or calls with retail partners. Lots of my meetings can be with the likes of Walmart – middle America – the fashion is very different to back home.

When I’m going out, I love to find unique pieces. I’m loving Mariam Seddiq dresses at the moment. I recently wore a bright yellow to my sister-in-law’s welcome drinks for her wedding and loved it so much I ordered it in two other colours. Something about the shapes of her dresses makes you feel your best.

No two days are the same for you - how does what you’re doing on a given day dictate what you wear?

As a new mum, this is very true for me. Right now I am largely working from home spending precious time with my 5-month-old daughter Noa, so it’s Alo activewear more often than not! I make sure whenever I’m in the US to get a new haul. Nothing compares to their leggings - they are a close draw with the Lululemon Align tights.

Fashion and beauty play a big part in your world - where do you find inspiration when it comes to a professional wardrobe? Who inspires you?

My team have great style. I’m often copying what they wear as they are far far cooler than me! I love the style of women such as Rosie Huntington Whiteley. Monochromatic looks have become the norm for me. I still have lots of colour in my wardrobe – but it is maybe worn a little less now.

What was the last item of clothing, accessory or adornment you bought to wear for work?

I recently invested in the Alaïa “Strass” studded ballet flats, and I am obsessed. They elevate any look.

Dan Ahwa is Viva’s fashion and creative director and a senior premium lifestyle journalist for the New Zealand Herald, specialising in fashion, luxury, arts and culture.

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