The Clothes Successful Men Always Wear, From Expensive Athleisure Pieces To Designer Denim

Alo Yoga

Rob Biederman, 38, is busy. He founded Asymmetric Capital Partners in 2021, now works as the fund's managing partner, and was named a BI rising star of venture capital in 2023.

He also serves as chairman for Catalent Technologies, the pharma and biotech company he previously founded.

Whether he's sitting in an office or on the go for a work trip, Biederman has found the $128 Day and Night pants from Alo Yoga to be the most comfortable and work-appropriate option on the market.

"I'm actually wearing them right now," he said during an interview with BI. "I might wake up in New York, fly to Boston, fly to San Francisco, then fly to London. So, I need things that can do well across multiple days. They can't get wrinkled if I wear them twice."

In his experience, Alo's slacks fit the bill. They're sold in four neutral colors, and each pair has four pockets.

Buck Mason

"They're two brands that I find to be such undiscovered players," Biederman told BI. '"And it happens that both of their stores are really close to my apartment in West Village."

He describes clothes from both brands as classy, stylish, and crafted with quality. Biederman said they also hold up well after airplane rides and busy days.

Buck Mason is best known for its jackets, button-up tops, and thermal layering pieces. The brand's menswear items range from $45 to $1,498.

Billy Reid, on the other hand, sells elevated basics like lambskin jackets, printed button-ups, and peacoats, with each piece costing between $68 and $1,998.

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Paul Hill, the 25-year-old founder of the art-tech company Strada, describes himself as a "big uniform guy."

He spends his days operating a New York City gallery and developing workflow management software for the art industry. So he prefers to keep his wardrobe simple.

"I'm just like, let me pretty much wear the same thing as much as possible every day," he said with a laugh.

The base of his outfits is always a pair of jeans from one of two brands. When he wants a classic fit, he wears New York-based DL1961, which sells sustainably-made pants that cost between $158 and $258 each.

On days when he wants to go high-fashion, however, Hill turns to Andersson Bell. Designer pants from the Seoul brand feature patchwork patterns, oversize pockets, and unique washes. They cost upward of $306 each.

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Sasha Bratyshkin, 28, formerly worked as an engineer at Facebook and now serves as the cofounder and chief technology officer of Housing.Cloud, a platform that helps students find housing.

In the summer, he enjoys wearing designer pieces from Dries Van Noten and Jacquemus. The latter is known for its cropped jackets, statement button-up tops, and graphic hoodies. Its menswear pieces cost between $150 and $4,590 each.

But at the start of the year, you can usually find Bratyshkin wearing Acne Studios.

"They have great sweaters," he said of the Stockholm-based brand. "It's a cozy line."

The average knitwear piece from the brand retails for $620.

Ssense

Since the end of 2024, Bratyshkin has been using the e-commerce site Ssense to find designer pieces at discounts — specifically ones that keep him warm in the winter.

"I'm having a little cardigan phase, so I'm shopping for a lot of that stuff on there," he told BI.

The website sells brands like Bottega Veneta, Comme des Garçons, and Stella McCartney and occasionally offers discounts you likely wouldn't find on the retailer's website.

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Reed Switzer, 24, created the fintech company Hopscotch, which helps small businesses pay bills more easily.

He wears Buck Mason's $158 chinos for work most days. On his days off, however, he typically wears jeans from the New York City brand 3sixteen, specializing in Japanese denim. Pairs usually cost around $250 each.

"It's really, really solid stuff," he told BI about the brand's products. "I always had issues finding jeans that I really liked, and this brand just kills it."

As for tops, Switzer gravitates toward heavyweight, good-quality tees. He's a big fan of the $158 ones from designer John Elliott.

"I think they're really great, basic, plain T-shirts," he said. "And the cut on them is always really nice."

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"Any time I need to be a little bit more dressy, Loro Piana, I think, is classic," Switzer told BI. "You can't go wrong with them."

The brand's suits can cost between $4,200 and $6,825 and are favored by celebrities like Andrew Garfield.

Switzer said he also enjoys the designer's trousers for work days.

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"Regardless of whether I'm staying in the house or I'm going out, you'll always catch me in some form of a Lululemon outfit," Bryce Grandison, a 27-year-old former real-estate analyst, told BI.

Now studying to become a licensed agent in his home state of Georgia, Grandison doesn't have much time to focus on fashion. So, he sticks with matching sets.

He especially likes the brand's jersey pieces, which range in price between $58 and $98, the $128 ABC joggers, and the $128 half-zip sweaters.

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Reed Waldman, 30, is a dermatologist and the CEO of Veradermics, a biopharmaceutical company he founded. During each workday, he wears his personal uniform: a blazer and trousers or a full suit with a tie.

"I don't think I've bought any brand-new clothes in several years," he told BI. "I am an avid shopper of The RealReal. I primarily wear Cesare Attolini, Tom Ford suits, and Hermès ties."

He discovered the retail platform when he first entered the dermatology field with only one suit in his closet. A colleague suggested he try some designer pieces from the secondhand site.

"I think I bought some navy Brioni blazer for $70, and I was like, 'This is so much cheaper than going to Macy's,'" he said. "And people were like, 'This is a really nice blazer. You look really nice.' So then I started buying a lot more dress clothes."