One of the most common questions I get from young or first time entrepreneurs is about dress code. They want to know what they should wear to investor meetings, conferences, and meetups. There is certainly no magic answer to this, but I thought I’d put down my thinking, as this seems to come up a lot. I will go through my brief philosophy then actually go through what I wear to each type of event.
It is probably the advice I give the most. Do what makes you feel comfortable. Ultimately people invest in you, work with you, quit their jobs for you, and make terrible sacrifices for you. You have to be yourself. To really be yourself, you have to feel comfortable, so dress how you feel comfortable. I am talking about personally and socially comfortable, not physically comfortable, don’t wear Ugz and a snuggie just because they are cozy. Don’t look homeless, and don’t look like Gordon Gecko. Bathe regularly.
There is definitely a bias toward casual in the bay area, business casual in Seattle, and cool guy casual in LA. These are the areas I know the best. If anyone has any other location specific thoughts (the expectation in NY is folks wear suits etc.. please let me know and I’ll include that info here). I don’t think you have to cater to everyone’s expectations, but it is definitely good to know what you are up against.
My Sliding Scale
Shirt: t-shirt, to short sleeve polo shirt, to cut and sewn untucked long-sleeve shirts, to cut and sewn tucked in.
Pants: Not so nice jeans, nice jeans, slacks
Footwear: Mucklucks, sandals, Pumas, loafers, dress shoes
Interviewing a candidate:
- t-shirt, not so nice jeans, mucklucks.
- Reason: Important to show what a “day in the life” is like. Don’t want the candidate to think we are something we aren’t, most days are extremely casual
Conference or meetup
- cut and sewn, not nice jeans, and flip flops
- Reason: You want to look as approachable as possible. The value in any conference/meetup is usually the relationships you make. Don’t look stinky, and don’t look slick. You want people to think “hey I can probably talk to that guy”
Board or advisor meeting or 1 on 1 investor meetings
- cut and sewn untucked, nice jeans, loafers
- Reason: Gives me confidence that “I look good” and am composed. Convey “having it together” and confidence.
- Depending on the location/nature of the group anywhere from what I wear in board meetings to business casual (cut/sewn tucked in + slacks + dress shoes)
- Reason: Clean, together, and sophisticated. I typically see folks wear suits for these type of events, by comparison I still look a bit casual. Often times in larger groups like this, you get folks who are a bit more “old school” and expect CEO’s to wear suits, I try not to set off casual alarms by wearing flip-flops.
Happy to add more occasions to this if anyone has any particular questions, but this is pretty much my life, and what I wear. Everything I do is deliberate, how I dress is no different. How you dress says something about you, whether you want it to or not. I urge folks to be conscious of this, and send the signal they want to send.