One question that always comes up when working with a client on a speech – usually late in the process – is what should I wear? I only have average Male Fashion Sense – which means I’m somewhere between hopeless and OK on a good day – but I have seen a lot of speeches and speakers, and I’ve learned a few rules. Follow these and you won’t go far wrong. And yes, these rules are in tension with one another – which is a fancy way of saying they are mutually contradictory. Sorry; you have to figure out what works for you. Fashion is complicated.
1. Always dress as well or slightly better than the audience. If you show up at a Silicon Valley start up dressed like a banker in the full regalia, suit, tie, and etc, you will be written off by that audience as a hopeless case. The chance that you will connect with them becomes vanishingly small. So you want to dress as well as the audience, or slightly better, but the emphasis is on slightly. You don’t want a big mismatch. If you dress worse than the audience, of course, you’ll simply look like you shouldn’t be there.
2. Dress consistently with your brand. This one is tricky, because there are times when that entrepreneur may want to put on the suit and tie – such as when you’re meeting with a banker. But to the extent that you can, you should dress to mirror your brand, or embody it. I’ve seen wildly uncomfortable entrepreneurs in an ill-fitting suit and tie who would have looked better in something closer to their normal garb. So if you’re a creative type, wear something that signals that. If you’re a boring banker, then wear the gray suit. If you’re a creative banker, please wear a little sign that says, “Don’t invest with me,” so that I can see you coming. Which leads me to my third rule….
3. Dress to feel like a million dollars. Whatever costume you end up with, you should think about how it makes you feel. If you feel great in a suit, or in a Versace dress with mile-high heels, then you should consider wearing that because if you feel confident, that will spill over into your presentation and your persona and you will present better. But….
4. Dress in something that allows you to move. A speaker needs to be able to move on stage, and some fashions restrict movement so severely that you’ll look ridiculous when you try to walk. That won’t work. You have to be able to get on and off – and around – the stage.
5. Dress like a grownup. Unless you are 12. Your costume needs to be appropriate to your age, ilk, and style. Don’t try to dress like a hip teen if you’re over 30 and are talking to a high school audience. The results will be tragic. Act and dress your age. What you wear signals your tribe; don’t try to join one through costume if you don’t really belong.
6. Dress strategically. Think about the audience. What accessory can you wear, or slight change can you make, that will allow you to stand out from the crowd, without looking freakish? A lot of Silicon Valley types wear suits (to show that they’re successful) but add brightly colored sneakers (to show that they’re still hip and rebellious). The costume you wear sends a message; figure out what you want to say with your style.
My advice is that every speaker needs to create a minimum of three on-stage wardrobes, consistent with your brand and the other rules I’ve outlined. First, The Full Fig. This is your top-of-the-line outfit, appropriate for the meeting with your bankers, or talking to Really Important People at Davos or the Real TED. It’s probably a suit or dress, but if it’s not, it should at least be – and look – expensive.
Second, The Upscale Casual. This outfit will work for many a speech and conference that takes place in a resort location with an audience that will be dressed in a variety of styles, with an emphasis on the casual and comfortable. It might be a sport coat, dress shirt no tie, and (expensive) jeans or trousers for the men, and the moral equivalent for women. But be very careful. I recently spoke to an IT group in Upscale Casual, and was astonished to find about half the audience wearing the Full Fig. Were they all coming from job interviews? I had to work twice as hard to establish my authority — my right to speak to them — at the outset. Clearly, my sense of the IT crowd needs updating.
Third, The Among the People. This is the outfit to wear when you’re going as native as you can, among the entrepreneurs, or the SXSW crowd, or any group that includes people who actually think about wearing Onesies outside. The audience will be dressed in ripped jeans and t-shirts, so if you show up in a suit you’ll feel alien and the audience won’t listen to you. You might wear expensive jeans, a casual shirt, and a sports coat or the moral equivalent.
The idea is that you are a temporary authority as a speaker and as such you need to signal that sartorially. The audience will expect you to do so. But if you show up wildly mismatched with the audience, communication will be difficult and your performance will not be judged on its merits.
This is a tricky subject to get right. I welcome suggestions, ideas, and input from both the fashioned-challenged and the experts.