Men Used to Have Wives. Now They Have Stylists.

Jay Buys’s wife changed his life with 10 words: “You know, you don’t have to just wear band T-shirts.”

Shirts from Nine Inch Nails and Thrice—for years, this was the bulk of Buys’s wardrobe. Were they awesome ? Yes. Did they make him look like the CEO of a successful web design firm? Not quite. “If I looked better, I would’ve felt better,” said Buys, 44, of San Diego. So he hired someone to teach him to look better.

For most, the term “stylist” brings to mind a celebrity dresser putting Timothée Chalamet in a bombastic red carpet outfit. But there is also an industry of white-collar stylists helping hapless corporate types find the right shirts and trousers for their daily lives.

For Buys, that guy was Patrick Kenger.

Kenger runs Pivot, a personal styling service, charging as much as $5,000 to remake your wardrobe. Kenger’s job is part Marie Kondo, part therapist and large part a personal shopper. He helped Buys retire the band tees at work, subbing them with Suitsupply blazers and Bonobos trousers.

The switch had a Superman-bursting-out-of-the-phone-booth effect on Buys. “I look like I know what I’m doing.” Strangers seem to think so, too. He was startled when a random 20-something at the grocery store saw his leather John Varvatos jacket and chirped, “I like your drip, bro!”

Today, strivers in tech, law and finance are wealthier than ever, but corporate dress codes have collapsed. The hoodie-clad billionaire has become a cliché. In the C-suite, Loro Piana sneakers have trounced dress shoes. Fleece vests have vanquished ties. At the same time, we’re in a new era of boardroom boasting.

Executives crow about their pay packages, their workout routines (looking at you Mark Zuckerberg!) and the rarity of their sneakers. To look like you haven’t bought new clothes since we all clutched BlackBerrys is to risk being lapped on the corporate ladder.

So, if you’re sitting there confidently dressed and accepting compliments on how well your pants fit, congrats! But there are many men who lack the skills to piece an outfit together. Stylists say their work has ballooned in the past decade as the range of options on what’s office “appropriate” has waylaid even confident corporate leaders.

“Men are very confused right now with the dress codes that have blurred the lines of formality,” said Jacci Jaye, a white-collar stylist in New York City for two decades, whose services start at $3,800 plus expenses. Jaye, who works solely with executives, said that many of her roughly 50 clients knew what they liked in terms of style, but had no idea how to achieve that look.

“I looked sloppy and I didn’t want to look sloppy,” said Raj Nangunoori, 36, a neurosurgeon in Austin. He spent working hours in scrubs, but out of them, he was adrift. “Even shorts, like I was never great at picking out shorts,” Nangunoori said.

Around a year ago, he googled in search of a stylist and hired Peter Nguyen, a former menswear designer turned $10,000 stylist. Nguyen’s entrepreneur- and tech-type clients are long on money, short on time and scant on clothing knowledge.

Nguyen’s first step is a lengthy questionnaire: What music do you listen to, what are your hobbies, where do you vacation? “I view my clients like they’re characters in a movie,” he said. They give him their background and Nguyen’s job is to outfit that character.

The pair landed on a neat framework for Nangunoori’s new look: What would Ryan Reynolds wear? Prosaic tees were swapped for polo-neck sweaters and James Perse chinos were tailored to fit properly. Nguyen got Nangunoori into a pair of Common Projects minimalist $500-ish sneakers. Most importantly, he convinced him to ditch his shopping mistake paint-splattered jeans.

“I can’t pull off what Travis Scott’s wearing,” said Nangunoori, relaying all his hard-bought wisdom.

Like working with a trainer, some clients are wary of admitting they enlisted a fashion guru. One CEO I spoke with who hired a stylist told his business partner he had done so, only to be mocked. After that, he decided “I’m not talking to anyone.”

“I never had my own confidence in going shopping and buying suits or dress clothes or even my weekend stuff,” said Nate Dudek, 42, an executive at a software company living in East Hampton, Conn. A “technology nerd,” Dudek wasn’t born with a strong visual sense. “That goes from everything from picking a wall color in my house to the way I dress.” His tees-and-jeans wardrobe was as spicy as a glass of milk.

In 2022, about one year before co-founding his own company, Dudek “set out to invest in myself” by hiring Cassandra Sethi, a New York stylist behind the company Next Level Wardrobe whose services currently start at $5,500. Dudek’s wife, who has “killer style” and occasionally shopped for him, took some warming up to the idea. “She was like, ‘Why? I’m so good at buying you clothes!’”

But Dudek wanted an objective outside advisor—someone who didn’t know him as intimately as his wife—to overhaul his closet. (His wife has come around, and is relieved to not be his unpaid personal shopper.)

He never even had to meet her in person. Sethi shipped him boxes of clothes and over a three-hour Zoom session they deduced what suited him best. The transformation, Dudek said, “was fairly obvious.” Colleagues commented that he was carrying himself differently in his new grey Ted Baker blazer, and Save Khaki United’s trim tees. “I felt it too,” he said.

It is a cliché—but a factual one—that in many relationships, the wife or better-dressed husband is the begrudging fashion consultant. Supreet Chahal, a personal stylist in Oakland specializing in tech guys, says many clients come in saying “my girlfriend tried to help me, my wife tried out on me, but she keeps dressing me the way she wants me to look.”

Marco Rodriguez’s former girlfriend didn’t shop for him, but did steer him towards Nguyen a few years ago. “She was like, ‘Hey listen, I know you hate shopping,” said the 39-year-old musician and entrepreneur in Austin.

And oh, he did. Rodriguez could never find pants that fit his “interesting physique.” When he needed new clothes, he had to force himself to buy them. His style was directionless. “ I knew what I wanted but I just didn’t know how to get there.”

With Nguyen’s assistance, Rodriguez landed on a sort of “Soho boho, I hate to say rockstar” look of low-key Justin Theroux-style leather jackets, Chelsea boots and pieces from Parisian label Officine Générale. The experience “got me out of my comfort zone,” Rodriguez said.

The mindlessness that comes from working with a stylist is enticing to efficiency-obsessed tech workers. “I don’t want to spend a lot of time thinking in the morning,” said Michael Peter, 53, a principal architect at Google in cloud technology. Previously, he dressed like your standard tech worker—jeans, tennis shoes, the odd Batman tee—but a lightbulb went off during one meeting when he watched a better-dressed colleague take charge.

“He walked in the room, he had gravitas,” said Peter. Striving for that same effect, he hired Sethi of Next Level Wardrobe. She directed him toward a “refined elevated casual look” of slender-but-stretchy Vuori pants (which accommodate his gym-rat legs) and James Perse polos. Rather than his girlfriend telling him what to buy, he says, she’s stealing his clothes “all the time.”

To be sure, all of this comes at a cost. Businessmen I spoke with view the hefty fees as an investment, like renting a well-appointed office.

“The cost didn’t faze me a bit,” said Aaron Preman, 48, who owns a roofing company in San Diego, and hired Kenger at around $3,500.

“He taught me a lot in a short amount of time,” Preman said. He discovered that wintery colours suit his olive complexion and that he really likes Theory suits and Zegna ’s $990 triple-stitch sneakers—he now owns several pairs. The cost of everything—the guidance, the clothes—has been worth it to Preman. “He could’ve told me $10,000 and I would’ve said, ‘Okay, when are you coming over?’”

Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.

This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.

Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.

Here are three strategies useful for functional families.

Intrafamily loans

It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.

But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.

If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.

To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.

In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.

If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.

Asset gifts

Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.

The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.

Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.

However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.

These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.

But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.

Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.

The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.

Sellner doesn’t worry about his children using the funds for another purpose.

“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.

Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.

Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.

Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”

Disclaimers

A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.

Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.

Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.

Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.

Men Used to Have Wives. Now They Have Stylists.

Strong family financial planning can help reduce taxes and support younger generations. From intrafamily loans and asset gifts to inheritance disclaimers, strategic cooperation can create meaningful financial benefits—when families have the trust and structure to make it work.

Intrafamily loans

Asset gifts

Disclaimers