The Agony of “What Am I Supposed to Wear to an Investor Pitch?!”

The Agony of “What Am I Supposed to Wear to an Investor Pitch?!”

I was having lunch with a woman recently who I’ll call “Dior.” Dior has been a senior executive in a number of large media corporations and is now starting her own company and thinking about outside funding.

We’d been having a lively conversation on different startup and fundraising topics and were finishing up, when Dior put down her salad fork and looked-up.

“I have one more question,” she said in deadly seriousness. “What am I supposed to wear?”

And so it is with one of the most agonizing questions female founders ask me. “What am I supposed to wear to a pitch?”

As Dior explained, the designer business suits she was used to wearing didn’t seem like a good choice when so many of the venture capitalists she was meeting seemed to be wearing jeans and sneakers.

At the same time, she didn’t feel like she could walk into a meeting looking like a 22-year old college student. And let’s face it, a hoodie and sneakers usually doesn’t really have the same effect on a woman as it does on a guy.

I’ll give you the same advice I gave Dior. There’s no one-size-fits-all answer to this question. A lot will depend on the investor you’re pitching to and the industry you’re in. What might be appropriate in a pitch for a fashion startup probably won’t fly in a meeting for enterprise software. A lot will also depend on what you feel good in.

Your look should reflect your business and industry. Are your customers urban professionals, stay-at-home moms, competitive athletes? Think about who your market is, and tailor your look to elements of who they are.

And as a practical tip, start with simple basics. A pitch is not a good time to overaccesorize or try out an edgy look. A pop of color or cool accessory can help to leave an impression, but it shouldn’t become the focus.

To give you an idea of what works for me, my everyday meeting attire is usually jeans, pumps, black turtleneck, tailored jacket and red watch.

What have you worn to your pitch meetings?

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