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How the Modern Man Should Dress, According to 6 Professional “Wardrobe Fixers”

We asked style advisors their fashion do's and don'ts, as well as their staple pieces for a clean-cut, professional look.

Taff Bakali Photography by Terri Glanger
Taff Bakali, a gentleman’s personal shopper at Stanley Korshak in Dallas.

A-list celebrities have stylists who dress them for everything from film premieres to their walks from the car to the airport terminal (yes, really). But who can civilian men of means turn to for their own personal clothing conundrums? A new breed of “wardrobe fixer” has arisen in recent years to hack the closets of financiers, tech moguls, entertainment executives and other elites.

Today, thanks to social media, C-suite execs who once went incognito are expected to be public-facing representatives of their companies, which means having plenty of judgmental eyeballs sizing up not only their business acumen but also their sartorial choices.

In other words, ill-fitting clothing and square-toed shoes are no longer acceptable. To make matters more confusing, the days of the suit as a trusty go-to are over—the nebulous term “business casual” rules the day, leaving many brilliant minds scratching their heads when it comes to dressing their bodies. So Robb Report asked a few of the country’s leading style advisors to weigh in on how a man of accomplishment should dress in today’s world. Here’s what we discovered.

Victoria Hitchcock

Victoria Hitchcock

Photography by Alanna Hale

Victoria Hitchcock Style, San Francisco and the Bay Area

Years in the Business: 25

Services: “Excavation,” or editing a closet; “Rejuvenation,” which is focused on building a wardrobe from the ground up; and “Lifestyle Optimization,” a full style upgrade.

Fee: $2,000 to $25,000

What makes you successful at your job?

“I don’t work with people’s posses,” says Hitchcock, who insists on dealing directly with clients. “I’m not a ‘yes’ person. I’m here to help you show your authentic self.”

What is the number-one mistake that men make?

“Getting bedazzled by brand name or price tag; these measures do not necessarily equate to quality. Also, men’s shirt lengths are always off. The cuff is too long, or on short-sleeve shirts it’s almost to the elbow. Some guys are still wearing a polo too wide, almost like a golf shirt.”

A car coat from Giorgi Armani

Photo: Courtesy of Giorgio Armani

Loro Piana’s Stafford jacket. ($5,995)

What’s the most common advice you give your clients?

“I ask people, ‘Why are you looking to upgrade? Are you going through a midlife crisis? Is it because you’re single and you want to step it up? Is it because you work with people who all look a little cooler?’ Figure that out. And no matter what you buy, make sure it’s comfortable and functional.”

What does every guy need in his closet?

“A cashmere version of a car coat or a peacoat, something soft and elegant—think Giorgio Armani, Loro Piana. Also, a leather jacket—every guy wants one. Everybody should have a really crisp, white shirt with a great collar that’s fitted, trim, in good-quality cotton.” As for shoes, she suggests a Chelsea boot. “Saint Laurent’s have been iconic since the ’50s.”

Saint Laurent's Iconic Chelsea Boot

Photo: Courtesy of Saint Laurent

Saint Laurent’s iconic Chelsea boot. ($945)

What are items that men in Silicon Valley, in particular, need in their closet?

“Hoka Bondi shoes: They are really cool but may be fashion-forward for some people. They’re insanely comfortable, like walking on a cloud of air. Plus, they add an inch or two in height!” Other stylish but subtler items Hitchcock recommends are sneakers from Maison Margiela, Lanvin or Golden Goose; Frame denim jeans; a Moncler puffer jacket and a Maurizio Baldassari vest.

Andrew Weitz

Andrew Weitz

Photography by Dane Deaner

The Weitz Effect, Los Angeles

Years in the Business: Officially five; pro bono, more than a decade

Services: Everything from a one-off “getting started” program for those who’d like “a taste of the services” to an annual retainer program.

Fee: $500 and up

You were a Hollywood talent manager and an agent at William Morris Endeavor; how did you get started in fashion?

“I was always known as the best-dressed agent, and it was because I wanted a competitive edge.” Clients and colleagues took note, and a new career was born. “It’s about standing out in the right way, minding your details, and appearing smart and in control of yourself. You’re branding yourself.”

Giorgio Armani's double-breasted blazer in checkered serge.

Photo: Courtesy of Giorgio Armani

Giorgio Armani’s double-breasted blazer in checkered serge. ($3,095)

What is the number-one mistake that men make?

“Old shoes that are worn out, or square-toed shoes. I see a lot of ill-fitting blazers that don’t sit on the shoulders right or are a little too long. Men who wear jackets from their suits as blazers, which is a no-no. Tailoring is the most common problem. People think the bigger the clothes you wear, the more you’ll hide your flaws, and that’s not the case.” The right tailor, Weitz notes, can elevate an item from looking off-the-rack to made-to-measure.

Tom Ford jeans.

Photo: Courtesy of Tom Ford

Tom Ford slim-fit white jeans. ($650)

What’s your favorite example of how fashion helped change a client’s life?

“I had a guy whose wife thought he was having an affair because he looked so good, yet she was also more attracted to him than she ever had been. And a month after working with this one executive, who was a messy guy but good at what he did, his ROI [return on investment] was 20 percent higher.”

Bill Bolling

Bill Bolling

Photography by Mark Mann

Sales Associate, Boyds, Philadelphia

Years in the Business: 40

Services: Personal shopping services at home; in-house tailoring.

Fee: Complimentary

Is there a piece of advice you give to every client that seems to work?

“Buy clothing that you’re not only physically comfortable in but mentally comfortable in as well. I don’t recommend wearing something that’s not a reflection of you or your personality just because someone else is wearing it.”

A classic dark Ermenegildo Zegna suit.

Photo: Courtesy of Ermenegildo Zegna

A classic dark Ermenegildo Zegna suit. (2,895)

What are the key pieces you think every man should have in his closet?

“My top five go-to items include a dark suit—I prefer charcoal; a solid-colored blazer or patterned sport coat; a pair of dark slacks; beige or white linen pants; and a nice jacket—three-quarter length, long enough to cover a suit. I like Zegna’s full line; it’s a brand that is classic in its appeal but with a modern touch. I also like Scuderi, a private label that we carry. It’s high-quality at a reasonable price point.”

A Brunello Cucinelli deconstructed jacket.

Photo: Courtesy of Brunello Cucinelli

A deconstructed Brunello Cucinelli jacket.  ($2,995)

What do a lot of men need in their wardrobes but don’t already have?

“Most men—especially younger guys— tend to not own outerwear. They think coats are worn strictly to avoid being cold. But in a professional environment, a coat is a ‘finishing garment.’ To me, this reflects someone’s thought process in business.”

Faran Sheikh

Faran Sheikh

Photography by Alanna Hale

Style Advisor, Wilkes Bashford, Palo Alto

Years in the Business: 18

Services: Personal shopping, in-house tailoring.

Fee: Complimentary

How do you start to make over a man’s closet?

“I say, ‘Let’s fit one shirt, let’s fit one jacket, one suit, the pants. Let’s make sure everything fits perfectly.’ They always want it fast, but I work with Kiton, and I have to tell them, ‘We don’t rush. This is a handmade garment.’ You need to make sure everything’s right, first.”

Versatile five-pocket trousers from Kiton.

Photo: Courtesy of Kiton

Versatile five-pocket trousers from Kiton. (1,095)

What do you order?

“Navy suit, blue suit, gray suit. White shirts. Kiton has seasonal fabrics that I use to make them suits and jackets for going out and having fun. Then I build out the looks from there. If a man doesn’t need a suit for work, I’ll give him five-pocket pants and put them with a nice sweater—a nice V-neck or crewneck. And a beautiful, elegant loafer.”

Do guys in Silicon Valley wear sneakers?

“If my clients do, they have to be really dark and understated—navy, gray, black, like barely black. No color, though, not even white. For running, yes, but not every day.”

Brunello Cucinelli dark sneakers.

Photo: Courtesy of Brunello Cucinelli

Brunello Cucinelli dark sneakers. ($795)

What’s your best piece of advice for men?

“I have to see the person, to see what size he is. If he’s a big guy, it’s one thing, and if he’s small, it’s different. I like to see the character of the man, what job he has. What is his social life like? I need to know what color his hair is, what color his eyes are, his skin tone. That’s how I pick the best colors for him. Everything is connected to the client’s personality.”

Bob Mitchell

Bob Mitchell

Photography by Mark Mann

Co-CEO, Mitchell Stores, Westport, Connecticut (and Eight Other Locations on Both Coasts)

Years in the Business: 28

Services: The store, family owned since 1958, offers house calls and will send over selections from your favorite brands or host VIPs before or after store hours.

Fee: Complimentary

Is there a big trend you’ve noticed lately?

“We are selling a lot of sneakers, but in the $300 to $3,000 range. Guys wear them with everything from jeans to suits. Something sleek from Lanvin or Cucinelli.”

Sneakers from To Boot New York.

Photo: Courtesy of To Boot

Sneakers from To Boot New York. ($350)

Is there some piece of advice you find yourself giving over and over?

“Fit is the most important thing to looking current. I think there’s a lot of misconceptions out there, like bigger guys thinking they can’t wear skinny pants, but they actually look better. Or we get guys who buy skinny pants, but they still want to buy a coat that’s really long, and it looks ill-proportioned.”

What should every man have that he doesn’t already own?

“You know the five-pocket jean style? We’re selling a lot of wool dress pants in the five-pocket style. I’m wearing a Cucinelli one today; Zegna does one. Also, very soft sport coats that feel like you’re wearing nothing. It’s an element of being dressed up but in a casual way. Don’t be afraid to buy something timeless and high-quality. Another thing on my list every man needs is a piece of Loro Piana outerwear. Our number-one coat for five years is a three-quarter-length waterproof navy cashmere. When people first see [the price, $4,595] they’re like, ‘Man, this is crazy.’ It’s an investment piece! You’re going to wear it 100 times more than anything else in your closet.”

Loro Piana outerwear.

Photo: Courtesy of Loro Piana

Loro Piana outerwear. ($5,145)

Is there a common mistake you come across?

“Length of pants. As the bottom of pants has gotten narrower, it should be shorter, or it just stacks on itself.”

Taff Bakali

Taff Bakali

Photography by Terri Glanger

Gentleman’s Personal Shopper, Stanley Korshak, Dallas

Years in the Business: 25

Services: House calls, doing closet assessments and sometimes bringing in a tailor to give items that extra little tweak.

Fee: Complimentary

What does every man need in his closet?

“A navy blue suit, and a charcoal one is a plus. A beautiful lightweight cashmere blazer you can wear all year round. A selection of white shirts—I have 20 or 30, because anytime I don’t have time to think about what I want to wear, that’s where I go. I love Kiton, but it’s an exclusive brand for a certain client.”

A Kiton formal jacket.

Photo: Courtesy of Kiton

A Kiton formal jacket. ($9,995)

Any advice for guys when they’re shopping?

“Bring your wife along, if you have one. I love to have wives’ opinions: If she says it’s beautiful, boom, it’s a done deal.”

Is there a must-have for guys in Dallas to wear?

“Honestly, it’s a blue blazer—from the new kid who just graduated to the guy who’s running a hedge fund. What matters is the quality of the blazer, though. You can have it in vicuña, but that can be as much as $25,000. I’ve noticed that people have been buying jackets in the color Bordeaux. The problem is that once you wear it one or two times, it’s been seen. You have to put it away for a little while.”

Marol white shirt.

Photo: Courtesy of Marol

Marol white shirt. ($850)

What’s the biggest change you’ve noticed in men’s tastes over your career?

“There was a time when no guy would touch a flat-front pant; now 90 percent of our store—all of our pants, really—are flat-front. And guys want tapered pants. When I started at Ralph Lauren, people wanted them bigger and fuller. And everyone wants to wear sneakers now. Cucinelli makes a cool one. Keep in mind they’re like $950, and customers will say, ‘Wow, that’s expensive,’ but they wear them almost every day.”

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