[citation needed] While at secondary school at the Liceo Scientifico Leonardo da Vinci in Milan, Armani aspired to follow a career in medicine, particularly after reading A. J. Cronin's The Citadel.

[1] After serving in the military for two years, Armani became a window dresser and sales clerk at La Rinascente, a department store in Milan in 1957.

In that same year at the store, he was responsible for showcasing the earliest garments of the innovative Finnish textiles, clothing, and home furnishings company, Marimekko.

His skills were in demand, and for the next decade, while continuing to work for Cerruti, Armani also freelanced,[3] contributing designs to as many as ten manufacturers at a time.

In the late 1960s, Armani met Sergio Galeotti, an architectural draftsman, which marked the beginning of a personal and professional relationship that lasted for many years.

This led to a period of extensive collaboration, during which Armani worked as a freelance designer for several fashion houses, including Allegri, Bagutta, Hilton, Sicons, Gibò, Montedoro, and Tendresse.

The international press was quick to acknowledge Armani's importance following the runway shows at the Sala Bianca in the Pitti Palace in Florence.

The information provided by The Museum of Modern Art gives an example of how in 1990 Armani supported the New York show, Pier Paolo Pasolini: The Eyes of a Poet.

Although, Pasolini was known for a plethora of things, knowing that he created works mostly in the form of film or writing shows another side of Armani demonstrating an example of his appreciation of the arts.

Armani established an innovative relationship with the fashion industry, characterized by the 1978 agreement with Gruppo Finanzario Tessile (GFT), which made it possible to produce luxury ready-to-wear in a manufacturing environment under the attentive supervision of the company's designer.

Armani's concern for the end user culminated in the development of a more youthful product with the same level of stylistic quality as his high-end line, but at a more accessible price.

These included television spots and enormous street ads, together with a house magazine that was sent out by mail to consumers, and faithful Armani Eagle wearers.

In 1980, Armani was involved in the costume-making of the film American Gigolo, specifically for actor Richard Gere who played the main character Julian Kaye.

After the frenetic expansion of the 1990s (sportswear, watches, eyeglasses, cosmetics, home, and new accessories collections), 2000, the twenty-fifth anniversary of the brand, saw a flurry of investment activity, including stock sales and the acquisition of new manufacturing capacity intended to increase Armani's control over the quality and distribution of his products.

An example is the Guggenheim Museum in New York hosted an exhibition of Armani's work – a first for a living designer – with an average attendance of 29,000 a week.

[8] In 2011, Armani became the first luxury designer to accept Livia Firth's Green Carpet Challenge to highlight sustainable fashion created out of recycled plastics and fabrics.

The 2022 "Josephine" collection, inspired by Joséphine de Beauharnais, incorporated paisley motifs with chalcedony and grey diamonds.

[11][12] His fine jewelry has since been worn by celebrities, including Sophia Loren, Brie Larson, and Brooke Shields, at high-profile events.

The Armani Hotel was opened in Burj Khalifa on 27 April 2010,[20] comprising the bottom 39 floors of the supertall skyscraper in Dubai, United Arab Emirates; it has 160 guest rooms and suites, and 144 residences.

[27] Armani also designed and introduced the EA7 range, a brand inspired by Ukrainian footballer Andriy Shevchenko, who at the time played for A.C. Milan and wore the number 7 jersey.