Wardrobe Do's and Don'ts for Looking Successful and Trustworthy

“Men should absolutely pay as much attention to their image, clothing and presentation as women do,” Dara Lamb, a leading custom tailor and manufacturer, tells ThinkAdvisor in an interview. “It’s a very critical part of gaining a client’s trust.”

Lamb designs for women exclusively, mainly leaders in banking, top financial advisors and upper and middle management.

But the Custom Tailors & Designers Association board member is also an authority on wardrobe strategies for men in finance.

In the interview, she serves up advice for both male and female financial professionals and warns of dressing blunders they’re apt to make.

“Wardrobe has the power to profoundly influence both your career and your audience. If you dress [strategically], it can almost pull you along to your goals,” says Lamb, who has helmed her own company in made-to-measure and bespoke apparel for more than 35 years.

Her designs are classics with “a modern element,” as she puts it, and equivalent in price to high-end designer fashions.

In our conversation, Lamb, a frequent speaker at such events as Barron’s summits and institutions including Harvard Business School and Columbia Business School, provides wardrobe techniques to generate trust from prospects as well as revealing women’s clothing choices that trouble male colleagues.

ThinkAdvisor recently held a phone interview with Lamb, based in Long Island City, New York, and Westport, Conn.

Her main wardrobe message to men in finance is: “Stay away from anything making a statement that somebody will either love or not like at all.”

Here are highlights of our conversation:

THINKADVISOR: How much thought should men in finance give to their business wardrobe?

DARA LAMB: Men should absolutely pay as much attention to their image, clothing and presentation as women do. It’s a very critical part of gaining a client’s trust.

Meeting their expectations [of your attire and look] gives them a comfort level so they can open up, enabling you to have a realistic conversation to understand how you can be an effective advisor for them.

Now that in-person meetings have resumed, does wardrobe matter more?

It’s a second chance to make a first impression, except now we know a lot more about the people we’re meeting for the first time.

When you meet a client, you want to understand their expectations. If you’ve had conversations with them on Zoom, you’ve already developed a relationship and can assess [them] much better.

So now is a really great [chance] to dress for opportunity.

You use the term “strategic wardrobe.” What does that mean?

Wardrobe has the power to profoundly influence both your career and your audience.

You have to take into account what you want to achieve and how you want to influence. [Especially for women], it’s almost like developing a strategic marketing program for your personal brand.

If you dress [strategically], it can almost pull you along to your goals.

How long does it take before a prospect takes note of your appearance?

Before you open your mouth about their risk tolerance, they’ve already formulated an impression of you.

A very famous investor said, “I make up my mind about a company as soon as the [leader] walks through the door. I know whether or not I’m going to invest in them before we shake hands.”

Another very high-level person in wealth management told me, “Men and women need to spend much more time on the proper fit of their clothing and invest in the right kind.

“It will tell people they’re experienced and have the confidence to manage someone’s money and make decisions for them.”

If a man is wearing a garment that’s too tight or too loose, other men will notice that. Men are extremely attentive to fit.

To look like you’ve been a success for a long time, invest in very fine fabrics because if you’re presenting to a wealthy, successful person, they’ll recognize that, since they’ve probably seen a lot of those fabrics and know their cost.

That said, I wouldn’t go overboard and wear something that makes you look like your fees are too high.

No 1 is to aim for [attire] that isn’t going to offend.

What type of clothing would convey, “Trust me with your money”?

It’s always best to err on the more formal side until you know someone.

And when times are difficult and challenging [like now], people tend to dress more formally.

How can a wardrobe create impact and influence?

In an advisory position, where someone is giving you a great portion of their money to invest, they have to trust you.

If you dress in a way that’s not authentic to you, they’ll see through that immediately.

Is the attire of male leaders in finance more flexible nowadays? Or is proper dress still the traditional suit, shirt and tie?

Wardrobe has become more flexible, but you’re always trying to thread the needle, in custom clothes especially, between what feels authentic to the wearer and what meets the client’s expectation.

You can put on a fancy suit; but if that doesn’t feel right to you and if a really causal outfit makes you feel you’re not buttoned up enough to make a good impression, you’re not being authentic.

How about male leaders in technology who wear casual outfits — often, t-shirts and hoodies. Have they paved the way for a looser wardrobe for advisors in finance?

It’s important for both men and women to research what the client’s expectations are for your attire.

You can look at how a company’s CEO or CFO, or their accountants, lawyers and consultants are attired; see what the COO wears to earnings calls.

What if you’re unsure of the expectation for the way you’re dressed, but the company’s wardrobe is casual? What’s appropriate?

For men, a nice pair of trousers, a pressed shirt and a sport coat will work really well.

A really good color for a sport coat is blue — not navy but a brighter blue. It’s a color that people don’t have a problem with, and it’s very popular today.

Don’t wear a plaid or pattern going in to see a client for the first time because you don’t know how they feel about that, and their reaction to visual things is going to be pretty much instantaneous.

What if the expectation is for you to dress casually — mirroring the firm? Suggestions? 

If you wear a polo shirt, wear a white one or a neatly pressed white cotton shirt.

I wouldn’t wear a solid pink shirt because some people don’t like that color. But you could wear a blue or white shirt with a colored stripe.