Some of the reasons why Steve Jobs always dressed the same are...

• Recognizability: Jobs wanted to have a distinctive and easily recognizable appearance. By wearing the same outfit every day, he not only became an iconic figure but his look itself became a symbol of his brand, just like his products.
  
  
• Psychological Effect: Wearing the same outfit can also have a psychological effect – it can help strengthen and solidify one’s identity. For Jobs, it was part of his personal brand and self-image as an innovator.
  
  
• Simplicity and Minimalism: Steve Jobs was known for his love of simplicity and minimalist design, both in his products and his personal style. He believed that a simple life, free from unnecessary distractions, could lead to more creativity and efficiency.
  
  
• Inspiration from Zen Buddhism: Jobs had a deep interest in Zen Buddhism, and this influence was also reflected in his mindset. Zen Buddhism teaches that less is more, and avoiding excess can lead to a clearer and calmer mind. This was also mirrored in his minimalist clothing style.
  
  
• Setting an Example for the Team: Jobs also wanted to serve as a role model for his team. Through his conscious choice of a minimalist look, he could show that it wasn’t about external appearances but about the work and spirit of innovation. He set an example for his employees that substance matters, not style.

Hairstyle & Beard

His hair was neatly trimmed and kept short, complementing his clean and professional appearance. Steve Jobs frequently sported a three-day stubble, which was always well-maintained, giving him a relaxed yet refined look.

Glasses

His glasses are the "Classic Round" and are made by the southern German manufacturer Lunor. It is a handcrafted product, "made in Germany."
The price for the Lunor Classic Round is 339 euros.

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It took a while for Steve Jobs to discover his Lunor glasses. He is said to have found them in 1998 in New York, by which time the Apple co-founder was already in his early forties. Apparently, it was love at first sight, and above all, with eternal attachment. According to the manufacturer, Steve Jobs wore the model "without exception for 14 years" – a truly remarkable period of time.

He was so impressed by the craftsmanship and quality of the glasses that over the years he bought additional pairs (Antique Silver and sometimes 18-carat white gold), said Sophie Fux, the chairwoman of the Lunor supervisory board, in an interview with the magazine "Spectr" (May 2021 issue, available on Readly). After Jobs passed away in 2011, the global demand for the Lunor Classic Round exploded, as Lunor board member Michael Fux reports: "It felt like everyone wanted the Classic Round. We began selling our frames in countries we had never supplied before.

Black Turtleneck
Clothing brand St. Croix suggested it played a role in the Apple CEO's iconic black mock turtleneck, while revealing that sales of the $175 shirt, which Jobs reportedly favored, had risen by 100%.
According to St. Croix owner Bernhard Brenner, Jobs would buy two dozen turtlenecks annually. He also mentioned that the Apple CEO personally contacted the company to share his gratitude for the shirt.
It was a myth that was swiftly debunked by a pre-published snippet from Walter Isaacson's biography of Jobs, which uncovered a previously little-known story about the friendship between Jobs and Issey Miyake.
The true creator of the iconic turtleneck was Japanese designer Issey Miyake.[www.thecut.com]
In the 1980s, Jobs visited Sony, and during a meeting with Chairman Morita, he asked why Sony employees wore uniforms.
Morita explained to Jobs that after World War II, many people had no clothes, so companies like Sony provided uniforms for their employees to wear at work.
It became a way to strengthen the bond between workers and the company.
Jobs wanted to create a similar sense of unity at Apple. He called Miyake and asked him to design a vest for the company.
Employees disliked the idea of everyone wearing the same clothes as part of a corporate uniform. So, in true Jobs fashion, he took the concept of a corporate uniform and made it his own personal style.

In 2017, Issey Miyake Inc. released something that could be described as an homage to the original turtleneck retired in 2011, though certainly not a reissue. The $270 Semi-Dull T was designed by Miyake protégé Yusuke Takahashi.

Seiko Quartz 6431-6030

In 2016, Heritage Auctions auctioned a Jobs watch, with the price rising to 42,500 USD.



In 2017, Seiko reissued the watch in a limited edition.
Unfortunately, the watch is only supposed to be available on the Japanese market.

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We can’t ask the late Steve Jobs now, but it is fun to imagine that the watch somehow influenced his design values. At the very least, it is safe to say it is representative of them – even though he was not known particularly as a “watch guy” and was often seen with bare wrists later in life. He possibly stopped wearing it when his own products became a more convenient and accurate way of checking the time. There are actually some Apple Watch clock faces that are close, if not identical, to the Bauhaus design of the Seiko Chariot’s dial, but a specific tribute to it would also be cool.

Levi´s 501

The Levi’s 501 is known for its classic, straight cut and durability – qualities that aligned well with Jobs' philosophy of simplicity and longevity.

99X line by New Balance

New Balance Chairman Jim Davis claimed that the original design concept came from Jobs himself, and the 992 was the late Apple co-founder's favorite.
But before that, he wore the 991 for years and only switched to the 992 in 2007. He initially mostly wore the New Balance M991GL Classic Grey.
New Balance sneakers are commonly called "dad shoes" due to their comfort and long-lasting quality. Their design is understated and practical, with neutral colors that don’t attract excessive attention.

Steve Jobs by Walter Isaacson (ISBN 978-1-4516-4853-9) původně napsal:

"I'm about fifty-fifty on believing in God," he said. "For most of my life, I've felt that there must be more to our existence than meets the eye."
He admitted that, as he faced death, he might be overestimating the odds out of a desire to believe in an afterlife. "I like to think that something survives after you die," he said. "It's strange to think that you accumulate all this experience, and maybe a little wisdom, and it just goes away. So I really want to believe that something survives, that maybe your consciousness endures."
He fell silent for a very long time. "But on the other hand, perhaps it's like an on-off switch," he said. "Click! And you're gone."
Then he paused again and smiled slightly. "Maybe that's why I never liked to put on-off switches on Apple devices."

R.I.P. Steve Jobs

I highly recommend the book "Steve Jobs" by Walter Isaacson. As a big fan of Steve Jobs, it truly inspired me. The book not only highlights the positive aspects of his life and career but also delves into the difficult and less perfect sides. It provides deep insight into his personality, his visions, and the challenges he faced in making Apple what it is today.