The gender-affirming style coach spreading trans joy – one empowering look at a time 

As a style coach with more than 20 years experience working with the LGBTQ+ community, Annaliese Cherry knows a thing or two about crafting an empowering and gender-affirming look that goes further than simply the clothes you wear. 

“A lot of my clients are women [who] are transitioning later. So they’ve been thinking about it a lot and they don’t know how to translate it,” Cherry tells PinkNews. 

For Cherry, style is the key word here, rather than fashion, which she feels is what is being “dictated” by brands rather than individuals themselves. 

“I don’t promote ‘buy this for this trend’ ever. It’s more, ‘Buy this because it’s practical and you’re gonna look hot, amazing and gender affirmed’.”   

The founder and head stylist of AnnalieseStyle, Cherry launched her business – now based in Los Angeles – in San Francisco in the 2000s and began by supporting the gay and lesbian community. 

Around 2016, people began asking her for help crafting looks which affirmed their gender – such as presenting as more masculine or finding something that expressed their non-binary identity. 

Her shift into working more with trans clients happened “organically within the community”, she says and offered her “another next level of how [she] can be of service” to queer folks. 

‘They look at themselves in the mirror and see the possibility‘

For trans people, the clothes they wear, the way they do their hair and makeup and the accessories they choose are an important way of expressing their authentic self to the world.  

While clothes are just a small fraction of the trans experience, the joy felt when an outfit just clicks is undeniable.

The road to that perfect look is not always easy, though. As Forbes has pointed out, gender-affirming lingerie is hard to come by in mainstream shops, while Sartorial Magazine‘s Liam Hill has noted how clothing is designed and cut with cis people exclusively in mind. 

This means finding clothes that offer a euphoric moment of self-expression can be tricky for those who are transitioning and they may be buying certain items for the first time. 

Orange Is the New Black even touched on the topic in its first season, when a pre-Litchfield Sophia – played by trans icon Laverne Cox – tried on a feminine outfit she bought in front of her wife, Crystal. 

The sparkly top, denim skirt and cowboy boots combo made Sophia look like Hannah Montana, Crystal told her. Sophia replied that this is what happens when she “shops for [herself]” because she “never got to be a teenage girl”. 

Crystal then said: “And you never will be. You should be dressing like a classy, grown-up lady,” before proceeding to offer her a form-fitting purple dress to try on. 

“Holy s**t, I look hot,” Sophia said, seeing herself in the mirror.  

Cherry is sometimes only the second person a client has told they are trans and she is “honoured” to be allowed to witness that self-actualisation.  

“They’re trusting me so deeply,” she explains. “We meet up and maybe I have got a whole fitting room of clothing for them or we’re meeting at the salon for the first time.

“There’s that moment of transformation, where they look at themselves in the mirror and they see the possibility, or they see their true selves, and it’s pure joy. 

“It’s why I do this work. It feeds my soul.”

Cherry is surprised that more stylists don’t offer similar services to clients in 2023. A lot of people she works with have previously used a salesperson at a department store to help them, but “that can only get you so far”, as a transitioning person might not feel comfortable using a public changing room and the sales staff will not know what they have at home. 

“Having somebody who really can guide you is everything,” Cherry says, citing the importance of having stylists out there who are either part of the community or true allies.

Trans people are ‘warriors’ 

Cherry’s work with and her commitment to the trans and wider LGBTQ+ community, comes amid growing anti-trans sentiment across the United States and wider world. 

In recent months, states across America have sought to crack down on the freedoms and rights of trans people, with politicians invoking legislation banning gender-affirming care, toilet access and participation in sports based on people’s gender identity. 

The legislation is part of an increasing panic which seeks to remove trans people from all facets of public life and paint them as criminals and child abusers. 

In the wake of this “toxic, frightening and horrifying” situation, Cherry says it is 100 per cent her mission to spread trans joy and support the community in any way she can. 

“Now more than ever people need just one person, or a couple of people, in their lives to say: ‘I see you. You’re beautiful. What can I do to help you feel the most authentic?'” she says. 

Outside her day job, she also offers styling lessons at LGBTQ+ centres and universities and holds clothing-swap parties for trans people as a means of further supporting the community.  

To her, trans people continuing to live their lives in truth and authenticity, despite the onslaught of political, emotional and physical attacks, are warriors. 

She explains: “We’re just go about our regular days, having a bad day at work, having to pay our taxes or our car breaks down. But we don’t have to think ‘Oh my God, my hormones are off’, or ‘My surgery got cancelled’ or ‘My whole family has shunned me’.

“They’re next-level humans, next-level warriors of just what it is like to be so aware and having to synthesise their feelings all the time. 

“I want to do everything I can to support, empower, uplift and create trans joy.”