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A Word with Dapper Tomboy

Updated: Jun 27, 2020

For Gabby Kirschberg, clothes inherently have no gender. As the founder and CEO of Dapper Tomboy, a popular queer style blog, fashion plays a large role in her self expression. A self-proclaimed tomboy, she expresses herself through simple black and white outfits. The timid CEO enjoys mixing menswear and womenswear to create looks that disrupt gender norms. Her style partner in crime, Natasha Jahchan, sticks to bold and edgy pieces like skinny biker jeans and collared shirts. After meeting Kirschberg through the blog, Jahchan later joined the platform as an administrator and event planner. Although it was initially an online space for Kirschberg to express her personal style, Dapper Tomboy quickly became a collaborative Tumblr blog and Instagram account.

In the following interview, Kirschberg and Jahchan discuss a variety of topics, from style inspirations to the current state of the fashion industry.

Q: What does being a dapper tomboy mean to you?

Gabby Kirschberg: It means expressing yourself through fashion and dressing out of the gender norm. Fashion is put in a strict men's and women's box, and it's time to break out of that.

Natasha Jahchan: It means being confident wearing what you want to wear and not caring about what other people might think. It means being a role model for other people who may be afraid to express themselves.

Q: What kinds of styles do you identify with?

GK: I'm not gonna lie, I always see what male models, artists or gay men are wearing. Someone like Troye Sivan, Harry Styles, Tan France or models I love like Giotto Calendoli and Denny Balmaceda. Since my fashion is so menswear-based, I like to follow the trends they follow.

NJ: I always like more artistic styles. I follow people on Instagram who challenge gender norms in clothing, whether they are male, female, neither or both. It’s always so original. I like looks that are different and unexpected. I usually follow styles that I like even if they’re not trends yet.

Q: How important is personal style to you?

GK: It's very important to me since I always have used my fashion to express myself. Even back in my middle school days, while trying to fit in with all the other girls, I still kept wearing what I felt comfortable in. I never let society or other people's perceptions change what I'm going to wear. For example, you'll always see me in a suit at a wedding or in masculine clothing at work. That's what feels honest to me.

NJ: Personal style is really important to me, because it’s a means of expressing who I am to the rest of the world. It took so long for me to be comfortable dressing the way I do, so I don’t take it for granted. I feel like my style speaks about me when I meet people, and it makes it easier for me to show who I am.

Q: Where do you lie on the gender spectrum?

GK: I feel [like] I'm an androgynous female.

NJ: I definitely identify as a woman through and through, but in the way I look, I like to play around. I love men’s clothes, so I rock them. I think you can have masculine qualities without having to necessarily evaluate your gender expression. I love women and I love being a woman. I think we can redefine what a woman means when we challenge it through fashion.

Q: How do you view masculinity and femininity in terms of clothing?

GK: I don't necessarily view clothing as masculine and feminine. To me, it's more about how you choose to wear it. I buy men's clothing and wear it in a more feminine way as well as the opposite.

Q: What are your thoughts on the current state of fashion, overall? Is it evolving to be more androgynous or is gendered clothing here to stay?

GK: There are things I like and don’t like about the current state. As much as I can hope it'll go, I think gendered clothing will continue to be around for a long time.

NJ: It’s evolving. I don’t know if I like the commercialization of gay culture though, but that’s a whole different thing. Fashion is starting to take genderless clothing into consideration, but I’m afraid it’s just going to be a trend like boyfriend jeans. Or one men’s fashion week show that has women in it just to make headlines. It would be cool if all labels were just taken off of clothes and there were no men’s and women’s [categories]. I’d be interested to see how the majority of people reacted to that. Honestly, I’m a cynic about this stuff and I think everyone in the end just wants to make money. If ungendered clothing were to become more prominent, I’d hope it’s queer brands spearheading it and not major brands just capitalizing on a trend.

Q: How do you think fashion overall has changed in the past few years?

GK: I definitely think it's changing into a more androgynous state. I feel it's changed more for men than women. Men have embraced more feminine trends like crop tops, short shorts, fanny packs, and sling bags. As for women's clothing, I don't think it's evolved.

NJ: My perspective is skewed, because I live in New York [City] and mostly hang out with queer people. So, I think everyone in the queer community just keeps getting more comfortable expressing themselves, and that signifies a shift in fashion overall I guess.

Q: What is your ideal future for the fashion industry?

GK: I think in an ideal future there would be a thinner line between what's considered men's and women's, boys’ and girls’ [fashion]. I would love a future where blue isn't a boy, pink isn't a girl, a dress isn't a woman, and a suit isn't a man.

NJ: Badass, queer women in the frontlines, on magazine covers. That’s what I’d want to see.

Q: What do you think about other prominent queer fashion blogs like DapperQ or Qwear?

GK: I love them! DapperQ is amazing. I love the fashion show they put on every year!

NJ: I’m definitely excited to see the DapperQ fashion show again this year.

Q: Is there anything you want to add?

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.

Photos Courtesy of Dapper Tomboy

You can read the Dapper Tomboy blog at

You can also follow them on Instagram @officialdappertomboy.



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