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Sapphic Flagging: The influence of Timberland boots on sapphic style

Robyn Exton

Oct 03, 2024

Sapphic Flagging: The influence of Timberland boots on sapphic style
  • Fashion items have long been adopted by different subcultures to say something, to express who we are to the world. Activist slogans have been plastered on t-shirts at protests for decades. Badges and patches proudly represent biker gangs — hey there, Dykes on Bikes, I love you, by the way. Sometimes, fashion items, like a pair of Timberland boots, can offer a simple statement to signal to others: I’m queer as hell, and I want you to know.

    For sapphics, expressing this part of yourself without saying a word is called sapphic flagging, and we’re here to help you make sense of it all.


    How fashion can help with sapphic flagging

    Shop the latest Iconic Collection from Timberland here

    You’re probably familiar with some sapphic style staples: flannels, cuffed jeans, carabiners—you name it. And then, there are those lesser-known fashion trends that may have been associated with sapphics at one time or another, depending on your exposure to pop culture. So much can shape your understanding of these trends, from region and culture to socioeconomic status and the era you live in! 

    Before dating apps and social media, sapphic flagging was not only a means of self-expression, but of self-preservation. How could we sapphics communicate ourselves safely without the risk of discrimination? For many queer folks, the only way to find each other was at bars, through newspaper classifieds, or by spotting someone sporting the right combination of clues: a leather jacket or maybe even a simple carabiner clipped to their belt loop. Fashion was one of the few ways to communicate identity in a world that didn’t always have space for queerness, and it allowed sapphics to find their people without saying a word.

    Today, we’re focusing on one fashion item in particular: the role of Timberland boots in sapphic flagging.

    Closeup shot of someone wearing the classic Timberland boots, hanging over a rooftop railing with a city skyline in the background.

    Source: Timberland


    Timberland’s origins

    According to Timberland.com, the brand started off by “equipping workers to power through the toughest outdoor environments.” This really speaks to the fact that Timberland is really a worker’s boot. They’re no Louboutins, all right. The iconic yellow boot came to be in the 1970s and, much like Timberlands, lesbian women seem to embody that same blend of practicality and durability.

    A 2014 YouGov survey of over 1,100 people found that lesbian women lead the pack when it comes to DIY confidence. 77% are confident in putting together IKEA furniture, compared to 58% of straight men and 48% of straight women. And it doesn’t stop there — 87% feel capable of unblocking drains, and 81% are comfortable putting up shelves. They even outpace straight men on some of these tasks. It’s a kind of hands-on resilience that echoes the spirit of Timberland boots, breaking down stereotypes about who’s handy and who’s not.

    A line graph shows how lesbian women seem to be more interested in DIY projects than heterosexual counterparts.
    In 2014, YouGov performed a survey with over 1100 participants, both LGBTQ+ people and heterosexual people, asking about lifestyle – including attitudes about DIY projects.


    Source: YouGov

    Shop the latest Iconic Collection from Timberland here


    Hip-hop and Timberland’s cultural impact

    Over the next two decades, Timberlands went from being a reliable worker boot designed to withstand harsh conditions to becoming a cultural staple in the New York rap scene.

    In the book Buying In, journalist Rob Walker writes, “the legend goes that the first ‘urban’ buyers of Timberland boots were New York drug dealers—guys who had to stand on the street all night and needed the best possible footwear to keep them warm and dry.” There’s a lot to unpack here, from the racial undertones carried by the term ‘urban’ — hence the heavy use of quotes — to how this association between hip-hop culture and Timberlands developed.

    A close up of someone hiking while wearing Timberland boots, showing how resilient and practical the shoes are.

    Source: Adventure Magazine


    Why Timberlands can be a tool for sapphic flagging

    You might be wondering at this point, where do the sapphics fit in all of this? 

    Well, women and non-men have always been part of the rap scene, even if they didn’t receive the same mainstream attention as figures like B.I.G. Artists like Da Brat, for example, made waves in the ’90s. Though she didn’t officially come out until 2020, rumors about her sexuality swirled throughout her career. As one of the most prominent female rappers of the decade, with hits like “Funkdafied,” she carried herself with confidence and style — often including baggy clothes and, yes, Timberland boots.

    While Timberlands remain a staple of streetwear or hip-hop culture — they are also a tool for sapphic flagging within the queer community. Mignon R. Moore’s 2006 article, “Lipstick or Timberlands? Meanings of Gender Presentation in Black Lesbian Communities,” explores how Black lesbians explore gender through their physical appearance, often using masculine-presenting clothing to express identity and attraction. Moore describes how these styles signal belonging and help structure interactions within queer social spaces​.

    Fast forward to 2017, and this tension between masculine gender presentation and societal expectations is beautifully captured in Ari Fitz’s short documentary “My Mama Wears Timbs.” The film follows Frankie Smith, a pregnant masculine-of-center woman, as she reflects on her identity while preparing for her first maternity photos. Frankie’s choice to continue wearing traditionally masculine items like Timberland boots during her pregnancy highlights the ongoing negotiation between identity and visibility. For Frankie, Timberlands are not just about fashion but about holding onto her sense of self, even in spaces where her appearance and pregnancy may challenge expectations​.

    A New Yorker wearing Timberland boots stands on the sidewalk at a Brooklyn intersection underneath above-ground subway tracks.

    Timberlands can symbolize resilience, defiance, and pride. They offer a way for queer Black women — particularly those who are masculine-presenting — to maintain a sense of agency and self-expression in the face of societal norms that often seek to erase or marginalize them. 

    Shop the latest Iconic Collection from Timberland here

    So what’s next for Timberland? By understanding its place in the cultural zeitgeist, Timberland has embraced the communities that have long associated with the brand. Timberland campaigns are starting to spotlight queer voices — and we love to see it. Most recently, Kai-Isaiah Jamal, a queer, non-binary poet, activist, and model, has used their platform to speak on issues related to gender, identity, and queerness while fronting Timberland’s campaigns. Kai-Isaiah Jamal has many career highlights, but one that stands out is being the first transgender model to walk for Louis Vuitton. Jamal keeps breaking barriers, showing resilience in their journey — an attribute that aligns perfectly with Timberland’s ethos of durability. 

    As a New Yorker myself, this is the boot we associate with hip-hop and New York City. I’ve been rocking a pair of Timbs for 10 years now — well before I knew I was sapphic — and at this rate, I’ll turn them into a museum piece before I let them go. Maybe there’s a secret club of sapphic New Yorkers who feel the same — because let’s face it, maybe Timbs have a way of sticking with us, even when we don’t know we’re sapphic yet.

    But what about you? What’s your queer fashion? Just as Timberlands have come to symbolize hip-hop, Black culture, and Black lesbian identity, what do you think the future holds? Fashion has always been a way to communicate, and the possibilities are endless — how will you use it to express who you are?

    Robyn Exton

    Robyn is the CEO & Founder of HER. Find her on Twitter.

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