How To Dress For An Investor Meeting

Why is it important to know how to dress for an investor meeting? They say that in business, your first impression really counts.

Whilst the most important thing to worry about when it comes to preparing to pitch your startup to potential investors is of course having a polished proposal.

But, the first thing investors will see is how you look.

What you’re wearing to meet Investors says a lot about you as an entrepreneur, how your business sees itself, and ultimately: whether you’re good enough and serious enough for investors to splash their cash on.

So, you should wear a tailored suit and tie, or is it hoodie and bathrobe time?

What you wear to a pitch is an extension of your brand. It sets the tone for the rest of your discussion with VCs and represents your vision for your business.

In this article, we’re going to go step-by-step on how to choose the right dress code to enhance your pitch.

The art of the deal is to tailor your appearance to match your business’s market sector and positioning you want to own in the prospective investors’ minds.

You’ll need to either play to the expectations of investors, or if your business aims to shake up the market, you might want to subvert VCs expectations.

Pick a style

Exactly as you would pick a theme and style for a pitch deck, you’ll need to select a dress style that reflects your business.

For example, if you’re heading up a finance or investment firm, investors would expect smart suits and ties.

There are two main routes you can choose when selecting your dress code: formal and casual.

Formal is our traditional suit and tie affair, whilst casual dress like polos and jeans might be great for a more relaxed tone. Understand how these basics work when figuring out how to dress for your investor meeting.

The Formal Route: Suits, Suits, and More Suits

A formal dress is perfect if you want to show how serious you and your business can be. If you’re a young entrepreneur, wearing expensive suits can help you look older and more experienced.

However, if you’re more seasoned, overdressing in formal attire can lead to a perception of being part of an ‘old-guard’ or ‘out of touch’. It’s a game of balance.

For suits, the fit is extremely important for the tone of your appearance. If you want to appear youthful and trendy, fitted suit types may. These suits are characterized by their narrowness through the waist and chest.

It helps people look sharp, giving a contemporary flair to your appearance. That’s where a modern or tailored suit comes in – depending on which side of the pond you’re from.

These are slightly looser than slim suits, but they still retain a narrowness at the waist. These suits are great for entrepreneurs who want to look forward-thinking and already successful.

Finally, we have the traditional or classic look. These suits sit relaxed at the waist and are a lot roomier. They can be a lot more flattering and comfortable but may be more old-fashioned.

Classic suit trousers are wider with no taper. It is a style that was popular in the 70s and 80s, but in our ultra-modern world, it may make you look outdated.

However, if you want to convey a traditional image – flairs and loose grey jackets may be the way to go.

For women entrepreneurs, the selection gets a lot more complicated.

The key to wearing a suit is often picking the right blazer. Choosing a blazer with a dark color (black, grey, or navy) can make you look professional.

If you’re packing a bold and unique pitch, why not pair that with a louder, more exciting color?

Opting for blazers with boxy shoulders can be imposing and too serious. For a more natural look, make sure your jacket fits comfortably over your shoulders.

An hourglass jacket can help you look sharp and modern, whilst a straighter jacket can create a more serious and corporate look.

As for pants or skirts, for business formal dress, you’ll want to match the fabric of your blazer and bottoms.

Although, if you want to appear more casual and ‘hip’, perhaps experimenting with color blocking can add some contrast to your look for excitement and jazz.

Keep these key factors in mind when working out how to dress for your investor meeting.

The Casual Route: Tailor Your Wardrobe To Your Target Audience

Dressing sharp is only one of the facets of building relationships with investors and earning their trust. Check out this video I have put together explaining in detail how to connect with investors.

There are many legitimate reasons why entrepreneurs can choose to underdress for investor meetings.

It boils down once again to your brand image. Here are some great examples where underdressing can help sell your ethos.

Social Media or E-Commerce Company

If you want to channel your inner Silicon Valley, underdressing with a shirt and jeans is a great way to look youthful.

A t-shirt may be a little too far, especially if you’re meeting older, more experienced venture capitalists.

But, if you’ve got a shirt with the logo of your start-up, that’s a great way to create some brand consistency.

Fitness

If you’re heading up a fitness start-up, you can be forgiven for dressing up in fitness gear for your pitch.

Most investors don’t like to see an entrepreneur in shorts, but pairing an Under Armor shirt with some jeans or khakis is absolutely fine.

If you’re a fitness attire start-up, wearing your best merchandise is crucial. It shows off what you’ve got to offer and proves instantly that you’re proud of your work.

Gaming

If you’re a game developer, you might want to play to an investor’s expectations of those in the gaming space.

A t-shirt and jeans or khakis would be entirely natural for investors used to dealing with developers, although we would recommend opting for a collared shirt or polo just to be on the safe side.

Fashion

Do what you preach – or more accurately wear what you preach. If you’re in the fashion and beauty world, you’ll need to dress up to impress.

Wearing a bold outfit can help you stand out and get fashion investors in love with your style before you even utter a word. Bright colors and interesting designs might do the trick. If you look good enough for the cover of Vogue, you’re doing it right.

As with sports attire, if your business is a fashion brand, you absolutely should wear your own merchandise.

Get creative with what you’re showing off and investors will appreciate the confidence you have in your products. Matching your business idea to your attire is the key element of how to dress for your investor meeting.

Why would you underdress?

Whilst for many situations business formal is a great dress code to follow, there are some real dangers of overdressing.

A suit and tie don’t match what an investor expects from, for example, a games developer or tech guru, and so overdressing could make you seem out-of-touch with the market sector you’re operating in.

Investors want to know the entrepreneur behind a business they pump money into properly understands their market sector and demographics.

Matching the target audience and managing their expectations is a great way to do this.

Don’t show off

By taking care of our dress codes when pitching, we’re trying to make a good first impression. There is one sure way, however, to put you in danger of creating a terrible first impression. That’s showing off.

Investors want to know entrepreneurs are smart with their money – as they want to know the funds they provide are going to be handled responsibly.

So, any indication that you’re not responsible with your cash might hurt your chances of striking a deal.

Here’s our simple advice: skip any expensive accessories like watches or ultra-premium designer belts.

An investor might see you rocking a Rolex and decide that you don’t need the money, or worse, you don’t deserve their money. It might have been a gift, or perhaps you got a really good deal on that Gucci belt.

An investor doesn’t know that, they might just see someone who’s frivolous with their money. You probably won’t have a chance to fix that bad first impression. Leave the designer goods at home and keep your accessories simple.

Of course, there are exceptions to this rule. If you’re a luxury watch dealer, for example, you don’t want to be found with a $20 Walmart watch.

If you want the wealth gains you’ve already made from your business to be a key selling point to investors, it could be part of your pitch to come bearing lots of gold – if that’s your brand.

Though, as a general rule, if you have no business being in the luxury goods market, don’t come to a pitch with anything too fancy.

Dressing Advice for Women

For women, keep your jewelry fairly simple. Unless you’re a beauty or jewelry company, you don’t want to wear anything that is too distracting.

A simple pendant and stud earrings will work wonders. Once again, if you’re rocking 4-carat diamonds, you might give off the wrong impression to potential investors.

For hair and makeup, let’s keep things simple. Settle on a makeup that you’re comfortable with – a pitch is not the time to try out a new look.

Anything that doesn’t stand out and feels natural to you is bound to be a good way to go. Going with your instincts is a great starting point for how to dress for your investor meeting.

Keep in mind that in fundraising storytelling is everything. In this regard for a winning pitch deck to help you here, take a look at the template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

Who are your investors?

When selecting the right dress code, you’ll need to keep in mind who your investors are, and what round of funding you’re meeting for.

In the tech world, founders rarely – if ever – walk around in a suit and tie. Tech investors are used to meeting with professionals wearing relaxed clothing.

So don’t be afraid to dress down. If your VCs are in the Silicon Valley space in the US or operating around Silicon Roundabout firms in the UK, you can ditch the tie to match their expectations.

If you’re at a pitch event, rolling up in business formal might make you stand out like a sore thumb – and not in a good way. For these events, you might want to follow what other successful entrepreneurs have relied on in the past.

These events tend to be more informal than one-on-ones, so tailor your dress accordingly.

It is important to keep in mind which stage these potential investors are entering at. An angel investor is much more likely to forgive a rough t-shirt and shorts than a Series-C private equity firm.

Always remember what your potential investor is expecting and play on those expectations.

Some angel investors love seeing founders wearing a t-shirt with the logo of their start-up as it shows drive and confidence in their brand.

Angels are looking for founders who have the stamina to keep at their business, so any way of proving you’re in it for the long haul is helpful.

When start-ups get to their first round of venture capital financing, they’ll start meeting with backers offering higher amounts up to around $5M.

Series A and later investors meet lots and lots of founders, so dress smartly to stand out from the crowd. Don’t wear anything too flashy, however, as investors at this stage are looking for sustainable and predictable businesses.

Flaunting Chanel does not always scream sustainable.

Once you’ve got VCs knocking at your door, you can stop worrying about dress codes. I don’t think Mark Zuckerberg cares too much about first impressions anymore.

Conclusion

There we have a comprehensive guide on what to wear to meet investors. Managing your dress code and appearance is all about creating a great first impression.

Once you’ve got the first opinion set, it’s time to wow investors with the rest of your pitch.

Continue those great impressions by tailoring your body language to convert your investors too. Make a conscious effort to learn how to dress for your investor meeting.

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