Aloha Rag opened its doors for the first time in 1991 on Kuhio Avenue in the center of Waikiki, Hawaii. The original boutique was humble in size and had a vintage American theme selling used clothing from classic American brands such as Levi's, as well as rare collectibles including toys and even candies. As time passed owner, Tatsugo Yoda decided to focus on clothing offering garments from brands such as Generic Costume, X-Girl and Milk Fed...which could be found nowhere else in Hawaii at the time.

Clips was established in 1993 in a retail space a couple of doors down from Aloha Rag in Waikiki. The goal of Clips was to offer its customers the best surfboards and surf products available. Clips also stocked a limited supply of skateboards and skateboard equipment.

With growth in mind, High Seas Incorporated was established in 1995 as the parent company to Aloha Rag.

In 1996, High Seas Incorporated ventured into the furniture industry by opening P Squared Showroom on Kapiolani Boulevard in the Blackfield Building. P Squared was founded with the intent to introduce Honolulu to truly contemporary furnishings, along side modern classics by the likes of Cappellini, Vitra, Herman Miller and Flos.

With a retail space opening up next to P Squared Showroom, Aloha Rag moved its boutique to Kapiolani Boulevard in 1997. The new location was more accessible for locals and tourists alike and was also more convenient for internal business operations being that High Seas' two storefronts were right next to each other. With the new location came new brands including high-end labels Martin Margiela and Comme des Garcons.

Along with the move of Aloha Rag's boutique, Clips also joined the row of stores on Kapiolani Boulevard.

In 2002, with an increase in the number of employees, High Seas Incorporated acquired and office space on the second floor of the Blackfield Building, almost directly above Aloha Rag and P Squared. In that same year, Aloha Rag also launched their e-commerce website– aloharag.com. Aloharag.com could now offer Aloha Rag's diverse selection of merchandise to customers abroad that were unable to travel to the physical boutique. The website was the first step in making Aloha Rag and international fashion destination.

With a steady flow of Japanese clientele, High Seas Incorporated established Hi-Press in Tokyo, Japan to aid in marketing and customer service in that region. Hi-Press also became the Japanese distributor for one of Aloha Rag's best selling jewelry brands Luis Morais.

In 2007, Aloha Rag tripled its floor space by taking over the retail space of P Squared and Clips. The newly renovated store became the Aloha Rag Honolulu flagship boutique that we know today, offering merchandise from famed fashion houses like, Lanvin, Yves Saint Laurent, Ann Demeulemeester and Dries Van Noten, along side cutting edge designers such as Alexander Wang, Henrik Vibskov and Golden Goose. The new look even included its own Balenciaga concept shop designed by the renowned fashion house themselves.

In 2008, it was time for Aloha Rag to open a second retail location. The obvious choice for expansion was New York City. The fashion industry lives and breathes in NYC and a New York boutique was always a dream of Aloha Rag's president Tatsugo Yoda. So, when the opportunity arose, Aloha Rag moved into a ground level space of an upper-class residential building on Greenwich Street. Many of Aloha Rag's designers had their own boutique in NYC so Yoda decided to feature what wasn't there...including Japanese brands Beautiful People, N. Hoolywood and Pester.

With demand for an in-house label, Yoda began designing the Aloha Rag Collection in 2010. The pieces were inspired by classic American basics and military garments, with the utmost attention being placed on materials and production. The collection debut for pre-fall/winter and gained recognition from international press.

While designing Aloha Rag's first collection, Yoda established the Aloha Rag Showroom/Atelier on Broadway, New York. The new showroom became a creative hub for Aloha Rag, offering an accesible space for photo shoots and meetings with other designers to work on collaboration projects. The showroom also represents Luis Morais jewelry and Pester clothing in the US.