This is an as-told-to essay based on a conversation with Amanda Massi, a luxury personal stylist based in Los Angeles and Las Vegas. This story has been edited for length and clarity.
I have always known that I wanted to work in fashion.
While getting my master’s in fine arts with an emphasis in fashion design, I got a job assisting a stylist to support myself and to pay for school. After about six months, I realized, “I can do this. I don’t need to assist anybody.”
I got in with the tech crowd just through word of mouth. I built up my own network and went to a lot of events. When one tech guy likes you, they tell their friends, and then they tell their friends, so it’s a very tight-knit circle. I was able to build a good foundation pretty quickly in San Francisco.
I’ve since relocated and work out of Los Angeles and Las Vegas. My clients are about 65 to 70% men. They mostly work in tech, finance, and real estate. The women that I style are also business owners or very philanthropic. I also work with celebrities and people in music.
I always find that when men seek fashion advice, they truly want to know the answer, but they are clueless, don’t have time for it, or are just really bored of grays and navy blues. Most of the men I style want a silent, confident look. Then I have a few who are extremely maximalist and very adventurous in their style.
Tech guys want to look good, but not have their clothes stand out
I definitely understand that part of the tech industry’s culture is, “I’m too smart to care about what I wear.” In San Francisco, initially, my tech guys would say, “Mark Zuckerberg doesn’t care what he wears.” And I would say, “That’s great. Good for them. But you called me, so you obviously care. Also, they have a B in their bank account, and you’re almost there, but you are not there yet.”
For men who work in tech or are leaders in finance and real estate, what they wear is very important. They are exhibiting their company and representing their employees and investors.
They’re already confident, but they just want to have that feeling of being exceptional, especially if the tech company is newer or they’re doing another round of investing. You need to look a certain way when you go into an investor room and ask somebody for hundreds of thousands or a million dollars. You can’t just show up in a ripped T-shirt or a Comic Con shirt.
For the most part, my tech guys are not buying that expensive of clothing, but they are investing in quality clothing that’s going to stand the test of time. They want things that are more neutral and that fit really well. They just want to look silent, confident, and polished, but not to the point where people notice what they’re wearing.
One of my biggest clients owns a huge tech company and only wears Cuccinelli and Zenya. He is very dressy for the tech world, but some things that he says make me laugh, like, “I don’t have time to put on a belt, so I don’t want any pants with belt loops. I only wear loafers. I don’t have time to tie my shoes.”
I only find that in the tech world. They are always rushed for time. They just want to lock in and get the day started.
An elevated uniform
I’m all for the T-shirt and jeans. That’s the tech uniform, but we can do a knit T-shirt instead of a cotton shirt. It’s going to fit you better, hug your body better, last longer, and look polished without trying. It’s more comfortable than cotton and also more absorbent.
Or let’s get a raw denim instead of a stretch denim, because the stretch denim is going to warp. It’s going to change, it’s going to hug you in places you don’t want to have hugged, whereas a raw denim is going to keep its form all day. So when you’re sitting and you’re coding for 10 or 12 hours, you’re going to stand up, and your jeans won’t have a droopy butt because you’ve been sitting and stretching your jeans all day.
They often don’t know these alternatives, like a knit T-shirt or raw denim, exist. They’re also extremely analytical, so they want to know the reasons behind these choices, not just the feeling behind them.
So we can do a uniform. That’s what Steve Jobs wore every day, and he looked nice. A turtleneck is a nice uniform. For clients who want an actual formula, we do that. Their closet looks like a beautifully organized store, with all the gray, blue, and white T-shirts lined up, and then the corresponding denim or slack, and then their shoes right underneath. They just go down the line every day, and that’s what they wear.
But it’s a better quality. It’s a better fit, it’s a different fiber. It’s something that was tailored for them. So when they put it on, it just looks much more put together than buying something off the rack.
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