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Venture capitalists in New York City are ditching Patagonia vests for statement jackets and designer sneakers. Here’s how 7 VCs are making personal style part of the job.

Poppy Harlow Worldwide Speakers Group
Thought Leader: Poppy Harlow
November 28, 2022
Source: Insider

How does a venture capitalist dress?

The standard answer: All Birds sneakers. Patagonia fleece vest. A copy of Yuval Noah Harari’s, Sapiens, in hand.

In 2019, an enterprising product engineer at the startup website AngelList thought those few items defined a Silicon Valley venture capitalist. He reportedly rolled them into a bundle that he jokingly tried to sell online for $500, according to Insider.

But now, some venture capitalists don’t necessarily see the merit in dressing like one another.

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At a summit of VCs in New York this fall, guests arrived in bright floral dresses, tailored pantsuits, slim fit jackets, and designer sneakers. It was the first time that many of the city’s dealmakers had gathered together since the pandemic began. The pressure to impress was palpable.

“There is such a wide range of people that come together to form our tech community in New York,” said Alexa von Tobel, founder and managing director of Inspired Capital, and one of the principal organizers of the summit. She believes the display of personal style is an important indicator of that diversity.

In a city like New York, the street fashion often varies from neighborhood to neighborhood. The concentration of artists — and the artistically minded — creates space for uninhibited expressions of style. And the opportunities for people-watching are endless.

Many of the city’s venture capitalists are taking liberties with their style, too.

For Sita Chantramonklasri, the founder of Siam Capital, a unique sense of style also pushes back against the visual archetype of who belongs in tech.

“There should not be any “standard” about who looks like, sounds like, or seems like, they fit into the typical profile of a venture capitalist investor,” she told Insider by email. “In order for us to be best positioned to capture a diverse range of investment opportunities, we also need to be a diverse range of investors.”

‘Good style’ is often synonymous with luxury brands, flashy insignias, and rarefied displays of wealth. For investors — especially those who work with up-and-coming founders — deciding what to wear can be a delicate balancing act.

“I work with founders and a lot of founders don’t have much money,” said Ben Sun, cofounder of Primary Capital, another principal organizer of the summit. “You don’t want to be the guy that’s wearing the $2,000 jacket. I’m still a little bit self-conscious because I’ve been there. I was a founder.”

Many of the investors Insider spoke to said they prefer to take a ‘high-low’ approach to their clothes: melding luxury pieces with more budget finds.

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Whether it’s a leather skirt, a pair of sneakers, or a fleece vest, most venture capitalists told Insider that their work style boils down to one thing: personal power.

“So much of what we call style is actually about gathering yourself for the work of the day and making sure you feel as powerful, and as effective, and as comfortable as you possibly can,” said Susan Lyne, co-founder of BBG Ventures.

Here are seven venture capitalists who take their style as seriously as their investments.

Sita Chantramonklasri, Siam Capital

How would you define your style?

I always optimize for cost-per-wear and consider product life-cycle extension. I often gravitate towards items that are high-quality and timeless, which reduces cost per wear (and is a smarter way to spend!) for everyday items. I also appreciate vintage finds, which are extended life-cycle products and almost always, a better bang for your buck.

Who are your favorite designers?

Another Tomorrow is spearheading this shift in the high-end womenswear space, delivering beautifully well-crafted minimalist investment pieces. I love their power suits. I am a big fan of Quince, Naadam, and Everlane. They are all great for high-quality affordable pieces. 

Has your style changed since you became a VC?

Given our fund’s focus, I have had an insider’s seat or backstage pass into the broken world of manufacturing, supply chain, and consumption infrastructure. This has made me even more of a conscious consumer in thinking about traceability, production ethics and pricing transparency.  

Chantramonklasri’s answers were sent by email to Insider. 

Anu Duggal, Female Founders Fund

How would you define your style?

Feminine with French influence. Monochrome looks, long dresses, lots of florals — anything with delightful and unexpected details. I love bold colors for work events like red and pink.

Who are your favorite designers?

Ulla Johnson, Sezane, Zimmermann, Johanna Ortiz, anything vintage Chanel. I love the thrill of a good vintage find — am a regular on Vestiaire Collective & The Real Real.

Who are your style icons?

So many amazing style icons to take inspiration from over the years starting with Coco Chanel, Diana Vreeland, Jackie O, and more recently, Amal Clooney.

Are the supposed tech cultural norms of hoodies and t-shirts falling by the wayside?

Venture capitalists in NYC look very different to those on Sand Hill Road. As the nation’s fashion capital, you see much more style and personality amongst the venture capital community — many of them have come from different industries outside of tech.

Duggal’s answers were sent by email to Insider. 

Alaina Hartley, Greycroft

Who are your style icons?

Anine Bing – a model and rock & roll singer who founded the eponymous Anine Bing brand – is a major inspiration to me. She effortlessly combines high with low, classic with edgy, and accessibility with luxury. I love her signature look of an oversized blazer, cool t-shirt, denim, and statement accessories.

Has your style changed since you became a VC?

I have become even more adventurous since entering the venture capital world 4+ years ago. I even dyed my hair purple! I’m proud that my style is an expression of my personality, and I think it also appeals to founders who value individuality and creativity.

Are the supposed tech cultural norms of hoodies and t-shirts falling by the wayside? 

“Capsule” wardrobes are very in right now, and dress codes have certainly become more casual with hybrid work — so perhaps the tech entrepreneurs wearing stereotypical hoodies and t-shirts were just ahead of their time! You won’t see me in a Patagonia vest, but I can appreciate some high-quality basics!

Hartley’s answer’s were sent to Insider by email. 

Susan Lyne, BBG Ventures

How would you define your style?

Classic. Simple. Modern.

How has your style evolved over time?

For the first couple of decades of my career to define yourself as a professional woman you wore pants and jackets — period. I had a lot of Armani. There was a uniform for women. You knew you’d be fine going into a meeting in a black Armani suit. Now, I wear I lot of skirts with a cashmere sweater. That’s become my current uniform. Or jeans and a really great blazer.

Who are your favorite designers?

I buy a couple of things that are pricey every season. Altuzarra I really like at this moment. Proenza Schouler I always like. There was a period of time where I bought a lot of Gucc i— less so now. I also buy a lot of stuff that is Everlane. Jeans can come from anywhere as long as they’re cut well. I buy t-shirts on Amazon.

Lyne shared her answers in a call with Insider. 

KJ Sidberry, Forerunner Ventures

How would you define your style?

My style is pretty classic. I travel a bunch, so I tend to stick to neutrals. Layering is a pretty key step to each outfit, but will often flash some color or accessories here and there for personality and fun.

Do you have a style motto?

“Try being a little bit of someone else.” Style is like music — a remixed expansion of what came before. Inject bits and pieces of other people’s fits to expand your boundaries and explore new territory.

Who are your favorite designers?

Jeff Sheldon (Ugmonk) and Alec Nakashima (Akashi Kama).

What is one misconception you want to dispel about VC culture?

Style change in VC is happening from the bottom up, not the top down. The sneaker game has come a long way and appears to be changing at a faster clip than anything else.

Sidberry’s answers were sent to Insider by email. 

Ben Sun, Primary Capital

How would you define your style?

A bit street. A bit eclectic. I’ll wear Levi’s jeans and Celine shoes.

Where do you draw style inspiration?

Just people in New York. New York people have such great style. The scene is just amazing.

Who are your favorite designers?

Acne, Celine, Prada, Gucci, Bottega Veneta — just got a great jacket there. I love APC stuff. I have these old Dior sneakers I got 15 years ago at a Barney’s sale.

What is one misconception you want to dispel about VC culture?

A lot of VCs now are less finance people. They’re people like me. I was a founder. I ran my own startup for 12 years. So, the profile of the person has changed. If you worked in finance, or you worked at Goldman Sachs, you’re not going to wear fashionable stuff because it gets really frowned upon. So, you transition and you are wearing the vest because it’s what everyone does.

It’s really the background of the new class of VCs that don’t come purely from a finance background that are willing to express themselves more. You have founders or startup operators that now become investors and because of that they have more style.

Sun shared his answers in a call with Insider. 

Alexa von Tobel, Inspired Capita

How would you define your style?

For as long as I can remember, I have been style and design-obsessed. From the vantage point of a repeat entrepreneur, I think I speak for many founders when I say that style, design, and innovation are all inextricably linked. The heart of innovation is improved design: How do you build something that not only looks great, but also functions effortlessly and solves the intended problem?

Do you have a style motto?

One of my mottoes is “get up, dress up, show up.” I think there’s an energy that comes from getting up early, putting effort into feeling your best, and showing up with a positive attitude for whatever the day may bring. It’s a fashion motto as much as it is a life motto.

Who are your favorite designers?

When it comes to designers, I love to support entrepreneurs building amazing brands, such as Ulla Johnson, Markarian, Brock Collection, Celine, Rag & Bone, Rivet Utility, Scanlan Theodore, Dannijo (I’ve known the founders since age 2!), and brands I’ve angel-invested in like Hill House Home and Something Navy.

I also love brands that are trying to bring their values into the heart of who they are…I’ve recently come to love Thousand Fell sneakers which are eco-friendly. All that said, I also love the timeless classics; Chanel is Chanel for a reason.

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