Dress for Success Even At Your Startup

Written By Jaye Goldstein

There has been a bespoke uniform everywhere I’ve worked. In academia, how you dressed signified where you stood in the hierarchy. The teaching staff wore jeans and kept it casual. The more institutional leadership you had, however, the more professionally you needed to dress. When I served in The Office of the President and Provost at Harvard, for example, it was definitely “Suit Land.” I was horrified when I realized, about a month into being there, that absolutely no one wore jeans and ran out during a lunch break to buy some slacks.

In the startup and venture world, there are some fashion “rules,” too. As NPR recently wrote “The Patagonia vest endures in San Francisco tech circles, despite ridicule.” I’m not going to lie: I bought myself some Vineyard Vines button-down shirts and a Patagonia vest when I started in venture capital. I noticed the “look” and decided I wanted to appear as though I fit in. I didn’t have a traditional VC resume, so I wanted to add credibility wherever I could - especially at the beginning.

Maybe this makes me petty or shallow, but I do think that what you wear matters. Part of what you’re doing is signaling that “you get it” by dressing appropriately for your role. You want people to immediately de-risk you when they meet you. First impressions are so important; you’re messaging success.

I think of it like this: if HBO was making a movie about my startup and I was cast in the role of “badass CEO,” what would the costume designer pick out for me to wear?

I’ll be honest that I’m not an innately fashionable person. I treat my wardrobe as if it were a business problem. I observe the people around me for cues, I research on Pinterest, and I start making a strategic plan for my closet. Which brands and items do I need to acquire? I try to get a bunch of staples that I can wear for a range of purposes from coffee chats to board meetings - sort of like a capsule wardrobe.

When I first started rising in the ranks at my first startup, I spent hours researching what my “look” could be. I literally searched for “professional women outfits” and put hearts next to the ones I liked until I started to see some patterns. I’m deeply practical about clothing so I was selecting for a clean look that is also comfortable; heels were (and still are) completely off the table.

I ultimately decided to go all in with the “classic preppy” look. It seemed, from my research, that if I got a few classy button down shirts, some pearls, and dark jeans, then I’d be in great shape. And the big thing that seems to elevate it all is putting in a few extra minutes to fix my hair nicely in the morning. Getting my nails professionally painted regularly feels like it's part of my "uniform," too.

You can pick whatever style works well for you. Wear heels if they make you feel powerful. Wear all black if that simplifies your life. I have a white dog that sheds a ton, so that would never work for me.

The point is: you have to put in some effort. People are watching you now. Your team is looking for you to signal to them how they should dress at work. Influential advisors are wondering if they should put their support behind you.

There’s so much risk innate in early stage startups. When I put a few extra minutes into my appearance, I feel like I’m de-risking myself and giving myself a confidence boost at the same time. Part of being a founder is “faking it ‘till you make it.” so, even if you have a little bit of imposter syndrome going on, dressing up in your “CEO uniform” can help you get your game face on and help you build. I’m a feminist and a woman and as shallow as it may seem, I do think that what you wear and how your present yourself matters - even in early stage bio + climate tech startups.

Here are my favorite places to shop for my "startup uniform:"

Jaye Goldstein
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