Learn more about our process & goals: Sustainability Plan

Meet Gabby Kirschberg – Founder & Curator of Dapper Tomboy

Meet Gabby Kirschberg, founder and curator of Dapper Tomboy, whose style blog and Instagram celebrates "people breaking barriers of gender biased fashion." Read about her work "Whether you represent as someone who is gender-bending, androgynous, alternative, or a tomboy this blog is to help you be yourself."
gaby kirschberg


When I started Kámen Road – I never set out to design masculine bags. I don’t design for one style type or one type of customer. When I met with retail buyers, many of them would say beautiful but too masculine. 

I did an Internet search for “masculine style” and and there I found it — the world of WildfangDapperQDapper Tomboy. Finally, the shoe styles that I loved – the SUITS. 

Today, I am excited to introduce Gabby Kirschberg, founder of Official Dapper Tomboy, who will talk about her work and her experience in fashion.

Kathleen Murphy: Tell us how you came to create your company. What did you want to achieve?

GK: I started Dapper Tomboy five years ago as a blog to share all the styles I liked and outfits I was wearing at the time, which happened to be a lot of ties and bow ties. People got attached to the blog pretty quickly and had asked to share their style as well. Once that happened, it grew into a community of individuals all looking to each other for style ideas and advice.

I was hoping to create a space for people who dressed the same way as me. Basically to show the normalcy of it. There are so many women all over the world who feel the same way about fashion. Everyone is looking for an outlet or space to express themselves and Dapper Tomboy gives them that.

Photo: Gabby Kirschberg, Founder of Dapper Tomboy

KM: Can you describe dapper tomboy style?

GK: To me, dapper tomboy means expressing yourself through fashion while dressing outside the gender norm. Fashion is put in a strict “Men’s” and “Women’s” box and it’s time to break out of that.

I think what makes being a dapper tomboy unique is the pride behind wearing an androgynous outfit. I love that people are so happy to share their outfits and are so welcoming of one another. 

KM: Are style definitions important to you? Your followers?

GK: I am not sure if I feel definitions are important. I think it’s more about identifying with the same thing, whether that be androgynous, tomboy, or LGBTQ.  It creates a community. 

KM: How do you think definitions of style get created?

GK: I think media has a big part in it, whether it be in a magazine, tv show, or movie.

KM: Do you wish that you didn’t have to define it?

GK: I do. If being a “tomboy” was seen as “normal,” there wouldn’t be a name behind it.

Dapper Tomboy
Photo: Gabby and Natasha, Dapper Tomboy Team

KM: I saw a recent Instagram post from Cameron Esposito. She wrote: “took me a long time to feel comfy trying on “masculine” items in stores so if that’s u, me too.”

I read a lot of the responses that were painful. Many people commented that they can’t try on clothes that they want because of a definition that has been put on them. 

Can you talk about this reality?

GK: I can say that it’s something I’ve experienced. It took me a long time to get myself to not linger from afar but just walk straight to the men’s section. I think since we are subjected at a young age to what is “boy’s” and “girl’s” or “men’s” and “women’s” clothing, and if we don’t fit in those categories then we don’t fit in at all. I remember recently looking at baby clothes and seeing a firefighter onesie then seeing the tag that said “boy.” It made me so angry because it’s so unnecessary. I’m fortunate enough to live in a place like NYC, where I don’t get judged often while shopping where I want, but I know others aren’t as lucky.

Tomboy Fashion

KM: How can we change this as brands?  

GK: I think it can just be as easy as adding more options for everybody. When it comes to something like a t-shirt, if brands wanted it to be unisex, it’s as simple as adding several different cuts like straight, curvy, slim.

KM: How does Dapper Tomboy support the LGBTQ+ community and LGBTQ+ rights?

GK: People who follow Dapper Tomboy come from all over the world. They really express themselves through fashion. These people have so much courage since some countries frown upon dressing like a tomboy. LGBTQ still has such a long way to go. LGBTQ fashion is something I hope can be part of the normalization. 

KM: I am raising a daughter. When my daughter and I shop, I find myself asking her all the time: “Who is this designed for?” “Do you truly love it?” Why? These very specific “beauty” images get into girls’ heads very early, and I want to encourage her to question as much as possible without taking away what is great about clothes and shoes and that is self expression.

I know that I asked earlier about style definitions but can you talk more about your experience with the connection between media and fashion?

GK: The connection between media and fashion is kinda a huge one. Media definitely tries to control the actions we all take. I feel we are lucky right now because I think women’s fashion is changing in media. We are seeing actresses in big movies wearing suits, like Cate Blanchett in Ocean’s 8 and Blake Lively in A Simple Favor. We also see women like Janelle Monáe, who have been breaking these barriers for a long time, finally getting recognition. My mom never truly pushed any gendered fashion on me. I remember at 8-years old wanting to wear only boy’s underwear and she was always willing to buy them. 

KM: What are you working on now?

GK: Dapper Tomboy just shot an amazing video with HOOKmedia! They are an incredible duo, Director Tess Forestieri and Cinematographer David Siciliano. We are so excited about it. It’s a fashion video that we are hoping will bring more visibility to the androgynous community. It really broadcasts the confidence and passion behind dapper tomboy. 

Video Credits
Concept: HOOKmedia – IG @hookmedianyc
Director / Producer: Tess Forestieri – IG @foresttess
DP / Editor: David Siciliano – IG @sicilianod
Suiting: https://thetailorynyc.com/
Location: Mosaic Astoria – @mosaicastoria
Music: Black Sheep by Gin Wigmore – IG @ginwigmore

KM: What inspires you the most?

GK: My family and friends really inspire me. Everyone is so supportive of me and each other. We are all are fighting for our goals and standing beside one another in this rough social/political climate. Also, the people who submit to Dapper Tomboy really inspire me. I just love receiving messages from people who realize they aren’t alone and that Dapper Tomboy helped them express themselves!

KM: Is there anything that you want to talk about that I didn’t ask you?

GK: I would like people to know that everything is a journey and takes time. Fashion identity is one of those things. Take your time to find out what makes you feel most comfortable.

KM: Thank you Gabby. You inspire us!

Androgynous Fashion


Start Your Journey

Wool Felt Laptop Sleeve

Premium wool felt & upcycled leather for this everyday essential

Made to Order:

Crossbody Bag

The quintessential leather handbag for size & strength

Made to Order:

Stay Connected

Sign Up for the Kámen Road​ mailing list. Join us in the Slow Fashion, Slow Travel Journey. Let’s learn, discuss, and contribute together!

This website uses cookies to improve your user experience and allow for proper administration. Read our Privacy Policy to learn more:  Privacy Policy