In 1969, Abington moved to Newmarket, New Hampshire[6] and focused on producing waterproof boots made with injection molding, capable of withstanding the winters of the region.

[19][20] The New York Times reported on the fashion phenomenon in 1993, stating, "Seemingly overnight, Timberland and companies like Carhartt Inc. and North Face, which have made their reputations on manufacturing authentic outdoor and work apparel, have, in the parlance of the street, become ‘dope’ and ‘phat’.

[24] Prominent artists who featured them in songs or music videos included Wu-Tang Clan, Mobb Deep, Nas, Tupac Shakur, The Notorious B.I.G., Busta Rhymes, Dipset, Rihanna, Drake, Kanye West, and Jay-Z.

[25][21] In a 1993 The New York Times article about "outdoor" clothing brands' cross-over appeal to Black and Hispanic inner-city youth, Jeffrey Swartz downplayed the importance of the urban youth market in Timberland's success, saying that the company concentrated its advertising on its core customers, "honest working people", adding that the urban market was not "sustainable".

[26] In an editorial in The Amsterdam News, Swartz denied the charges of racism[27] and met with Black cultural leaders to explain Timberland's position.

[29] The company's Path of Service program, first established in 1992, allows employees to take up to a week per year of paid leave to engage in local volunteer projects.

[33] In 2022, Timberland introduced the Timberloop product take back program, which gives customers the opportunity to return used footwear or clothing to be recycled or refurbished for resale.

On Earth Day 2022, Timberland launched the Timberloop Trekker, a boot designed to be fully disassembled and recycled at the end of its life.