For men working in the tech industry, fitting in usually means subscribing to a style aesthetic — that is, wearing the Silicon Valley uniform, which consists of a plain T-shirt, jeans, and austere sneakers. Thousands of aspiring tech entrepreneurs mimic this look, often worn by tech icons like Mark Zuckerberg, Jack Dorsey, and Evan Spiegel, in the hopes that they will eventually earn similar cachet.

But dressing like you don’t care without actually looking sloppy is, in fact, an art. And so for the past two decades, men in the tech industry have turned to stylist Victoria Hitchcock.

A Bay Area resident, Hitchcock started her personal styling business at the peak of the dot-com boom in 1999, after working in business development and sales at several big tech companies. These days, she dresses employees at Facebook, Uber, Google, and Apple, as well as venture capitalists and investment bankers; she also dresses newly minted tech guys looking to “go from boys to men,” as she describes it.

Most of her clients live in San Francisco and the Bay Area, although some live in cities like Chicago. No matter the geography, though, the battle is usually similar: convincing clients to abandon geeky Casio watches, ratty Converse sneakers, and juvenile tees from college in exchange for clean menswear from brands like John Varvatos, James Perse, Zegna, Brunello Cucinelli, AllSaints, and Y3.

Many of her clients have zero fashion sensibility, she says, and need plenty of hand-holding during personal shopping sessions, while others turn to her to enhance their closets as they prepare for career upgrades. What both these types of clients have in common, though, is cash flow — and they don’t mind dropping tens of thousands of dollars on clothes, so long as they keep up with the image of looking good.

Over the summer, I sat down with Hitchcock for lunch in San Francisco to talk about Silicon Valley’s evolving uniform, how she soothingly but firmly tells clients what not to wear, and the most important items of clothing every man needs to own. These are the secrets of a Silicon Valley stylist.

This interview has been edited and condensed.

Chavie Lieber

How do men in the tech industry find you?

Victoria Hitchcock

Mostly by word of mouth. I’ll get referrals from clients’ friends who noticed that their buddy was dressing differently. I also get calls from wives and girlfriends asking for my help. In the past, I’ve worked with Hollywood creatives, research scientists, bankers, and lawyers, but over the last few years, the number of clients who are working in Silicon Valley has exploded.

Chavie Lieber

How much do you charge for your services, and what comes with them?

Victoria Hitchcock

My fee starts at $2,000. I start with a meeting over Skype, where I identify a client’s needs, like a total closet renovation or small outfit rollouts. Then I’ll do a closet meeting, where I come to their house or office, or have another Skype call to look at what they own. We spend a lot of time talking about what they like and don’t like, and I also ask for photos from two and five years ago, so I get to know them; I also ask that they do their own bit of research too. Once I have a full picture of his closet and personality, we discuss style goals and recommendations, and then I go shopping.

I also build virtual closets for my clients. I track everything they have and when they send me their schedule, I create lookbooks for their conferences, workweeks, or vacations. It’s a concierge service because I’m able to suggest things for them to buy, and I also add little reminders in their calendar, like, “I’m putting in for next January that these sneakers need to be replaced.”

Chavie Lieber

What’s the average age of your clients?

Victoria Hitchcock

I work with men of all ages, and they all have different needs. A lot of my younger clients, for example, want to look professional because they are dealing with people who are double their age. They have to look good, and they have to look really good if they want to get that financing or grab a room’s attention.

If they’re in [fintech], they are dealing with doctors, scientists, and researchers at Ivy League institutions. I’m sorry, but you can’t be taken seriously by these type of professionals, or raising money from investors, when you’re wearing an old T-shirt! So I am constantly getting this question: “How do I make myself look respectable to higher management in tech?”

Chavie Lieber

What about your older clients? What do they typically want?

Victoria Hitchcock

Usually, they are stodgy former Wall Street guys who’ve landed big jobs in tech but are uncomfortable wearing anything other than a suit. But they’re upset, right? Because they look around and go, “Oh, my god, I’ve got to work with the brains of all these companies, and they’re all so young!” It’s a harsh reality to face. So they come to me and ask, “How do I shave off maybe five or 10 years but still look like myself?”

Chavie Lieber

Do you abide by the minimalist aesthetic that Silicon Valley is mocked for?

Victoria Hitchcock

We call it effortless style, and yes, that is my approach. I want my clients to look like they don’t care.

Chavie Lieber

But what’s the difference between that and wearing an old hoodie and ratty sneakers?

Victoria Hitchcock

There’s a difference between “not caring about fashion” and “not caring about yourself.” I want them to invest in themselves. I also know that if they dressed like they cared about style, it would look strange. That’s not what this world is about. If you worked in computers your whole life but then you wear a really cool outfit to a presentation, the appearance just doesn’t match.

Chavie Lieber

So what is it about Silicon Valley and tech culture that promotes this type of appearance?

Victoria Hitchcock

There’s are a lot of messaging that’s being conveyed, because Silicon Valley is highly competitive. It’s filled with smart, ambitious, successful people, and careers are front and center here. People want to be taken seriously for their minds and productivity, and so they leave the flashy styles up to Hollywood, because people in that industry aren’t known for brains. Here, their fashion choices need to support a very specific lifestyle: They want to look transitional, cool, and like they could promote peak performance. In a word, being effortless really means I am competitive as hell about my skill set, but I am also cool and nonchalant, can’t you tell?

Chavie Lieber

So it’s almost the opposite of power dressing?

Victoria Hitchcock

Dressing effortlessly is a way to show off your shit, to demonstrate that you have brain power. I mean, I certainly could dress them to a tee, but it isn’t what the look is about. Instead, I’m kicking up the techie a few notches and making it sexy.

Chavie Lieber

With styles like Mark Zuckerberg’s, men in tech have developed a reputation that they are lazy about fashion. Is that true?

Victoria Hitchcock

Maybe a decade ago, it was. But today, they care. They’re interested in it because there’s a lot of people competing in their fields, and they have to look good to compete. They are also making more money than ever. They are all making several hundred thousand dollars a year, and they are spending all that cash; they just don’t want you to know they are doing it. They’re actually way more into luxury fashion than you think.

Chavie Lieber

Do you have a hard time convincing clients to spend money on fashion?

Victoria Hitchcock

Almost never. Sometimes a client will need to warm up to the whole thing, in which case I start off by focusing on what he immediately needs. But off the bat, he is going to spend $3,000 to $5,000 for just the basics, and honestly, it’s not an issue. It’s also worth mentioning that the price isn’t about labels. Higher-end clothes means pieces that pay attention to wider hips, longer torsos, bigger calves. All I need to do is have them try on the clothes and they notice the difference.

Chavie Lieber

What brand of watches do you recommend your clients wear?

Victoria Hitchcock

I think watches are really important because the perfect one will look good, no matter what you wear. I find myself confiscating a lot of Casio watches and G-Shocks with huge faces. A lot of guys also love to wear Tag Heuers that are two-toned and shiny and … yeah, those have to go too. I try to upgrade their styles and recommend watches from Omega and [Officine] Panerai. For dressier pieces, I go for Vacheron Constantin and Patek Philippe. I also really like Devon, which has really cool styles for the machine enthusiast. Those can cast about $30,000.

But that doesn’t mean I only recommend luxury. I also really like Nixon, and you can buy one for under $100.

The thing about men with money, though, is that watches can be tricky. I find that they like big, statement pieces, but I don’t want them to step into tacky territory. It’s okay if they want an expensive watch, but I want it to look simple. So no Rolexes. They are gaudy, and they don’t look effortless. I find myself doing psychology about Rolexes often, actually. I’m like, “Well, let’s talk about your ideas about Rolexes and why you want to wear a platinum watch with a white face?” And then they say, “Because my dad wore one and I want to live up to him!”

Chavie Lieber

What about shoes? Do you have any wisdom you can share in that category?

Victoria Hitchcock

I try to get my clients to wear dress shoes, which isn’t easy because they associate them with suits and ties. But there’s a whole world out there. I love loafers, I love wingtips, and I also love boots. Guys get very emotional over their boots, though. It’s a very sensitive area. If they’ve had a pair for five years, and the amount of wear and tear has them looking 10 years old, I still can’t get them to give them up. What I usually try to do is get the latest version of that boot, or introduce them to nicer ones. You can never have too many pairs of Fiorentini & Baker boots.

Chavie Lieber

What about sneakers?

Victoria Hitchcock

I do like sneakers, but that’s another area where you have to be careful. Let’s put it this way: I’ve seen a lot of Vans, and I am over them. Same with Allbirds. When I see someone wearing Allbirds, I say, “I respect your choice, but that was a big leap a year ago and it’s time to move on.”

Adidas and Nike make some really cool sneakers, and I also lean toward sneakers from Louis Vuitton and Gucci, so long as they are subtle. I personally don’t like all-white sneakers and don’t think they should be worn anywhere except on a yacht.

Above all else, though, sneakers have to look flattering on a man, which is why I often recommend the brand K-Swiss. They’re flattering because they are cut low on the ankle, and a lot of guys have thick ankles.

Chavie Lieber

How do you feel about big, chunky sneakers that are popular now?

Victoria Hitchcock

With the right outfit, it can be pulled off. I actually work closely with a guy named Matts Benson, whose whole business is finding rare, awesome sneakers for clients.

Chavie Lieber

What are some unique issues you have with dressing older clients?

Victoria Hitchcock

Some of my guys in their 40s or 50s have big bellies. A big misconception they’ve been fed is that they can’t wear anything fitted. They are touchy about it too, because they are photographed a lot and are the public faces of a company. They don’t think they can wear T-shirts if they have a gut, and stick to button-downs instead. So it’s a lot of me finding clothes that work for their body. A lot of them have stayed away from nice denim, when really, they should have never been wearing Dockers. In reality, brands like Fidelity and James Jeans make really good denim for guys with bigger thighs. Zegna also makes really wonderful five-pocket pants that are very slimming.

Chavie Lieber

Are you ever wary about creating tech drones who all look and dress the same?

Victoria Hitchcock

I try to stay true to people’s personalities, or at least help them develop their taste. I have a baseline of how I want them to dress, but I also keep in mind very specific details, like if they’re getting a major promotion or if they are struggling with aging. I am also hyper-aware of styles that come with ethnicity and culture. My Indian clients, for example, have a specific style of their own that I wouldn’t want to mess with, but I can recommend better glasses or shoes.

Chavie Lieber

Do your clients ever seem interested in algorithm-based services like Stitch Fix or Amazon Style Echo?

Victoria Hitchcock

No.

Chavie Lieber

Well, that’s ironic, given that I imagine some of your clients work with algorithms. Why won’t they try it?

Victoria Hitchcock

I think those services are trying to get people to constantly be buying things, but my philosophy is about fewer, better things. I think those services are for people who want a big wardrobe and want to be trendy. My guys are trying to look like they don’t try.

Chavie Lieber

Do you ever help your clients with grooming?

Victoria Hitchcock

I do, and I’ve seen attitudes shifting toward it too. Five years ago, my clients wouldn’t be caught dead with a blow dryer, or using product, but today a lot of them do. Some of them who are going gray early will also dye their hair, except no one is allowed to know about it.

All of my clients want facial hair, which I’m fine with. I think it gives men an approachable look, but can also feel a little mysterious. And I happen to love scruff, especially when there’s a little gray showing. So I’m okay with facial hair, as long as it’s short and not an overgrown, curly beard — although men these days love to call anything a beard after growing it for 10 days.

Chavie Lieber

Is there someone in tech who you think needs your services?

Victoria Hitchcock

I think I could lend a hand to Mark Zuckerberg. I liked seeing him wearing a suit [to testify before Congress about privacy issues] because it showed effort. I really think he should try harder. In my opinion, he needs to really mix it up with more modern outfits and colors, instead of being a dinosaur. He’s always stuck with the same types of T-shirts and pants. I think he can experiment with V-necks, try a cooler boot or pants that aren’t denim. Especially now, if he’s trying to communicate that there’s an old Facebook and a new Facebook, then the guy from those two should differentiate themselves. One of them should be approachable!

Chavie Lieber

Is there anyone in the tech space whose style impresses you?

Victoria Hitchcock

Jeff Bezos impresses me. I’m impressed that he looks better and younger, which is something he’s clearly been working on through exercise. But also he chooses clothes that show off his neck and shoulders. Elon Musk is another. That man looks superb in a tux, and if I was his stylist, I would recommend he invest in better bomber jackets because they do great things for him.

Chavie Lieber

What are some trends you’re seeing floating around Silicon Valley now?

Victoria Hitchcock

People have moved on from the hoodie and are now obsessed with vests. They throw on vests like it’s a blazer. I personally am not a fan because I think it adds on weight, but it definitely is practical with the weather here.

Chavie Lieber

Do you have any die-hard fashion no-nos?

Victoria Hitchcock

Nobody should be wearing khakis. I don’t even care if you’re on the East Coast. There are other color options, like dark olive green. Also, I don’t ever, ever, ever want to see flip-flops. Period. Okay? I don’t care if they are rubber or leather, and I don’t care if you are “just wearing them to your friend’s barbecue on the weekends.” No, you’re not. You look ridiculous.

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