Dasha Guyton on running a feminist business


Dasha Guyton wears many hats. She’s the woman behind Windy City Wardrobe, a fashion blog and personal styling service that empowers women to create a personal wardrobe that they love. She’s also the founder of Feminist Speakeasy, an intersectional feminist gift shop that helps you channel your outrage at Trump’s America into something positive. Every purchase you make with Feminist Speakeasy supports multiple women-owned businesses because Dasha collaborates with women makers and designers to create and curate her selection of gifts. We had to learn more.

Tell us about yourself. Who are you and what is Windy City Wardrobe?

I'm a wife, sister, daughter, feminist, friend, entrepreneur, and by trade, a legal assistant specializing in intergovernmental child support law.  Six years ago, my wife and I left everything and everyone we ever knew in Oklahoma and moved to Chicago.

To keep some sense of normalcy in a new city, I started my days with coffee and breakfast at Starbucks or Chick-Fil-A but the baristas refused to take my order before getting answers to their questions about my hair, clothes, and makeup. Since I’m a “but first coffee” kind of girl, Windy City Wardrobe was created as a solution to this problem. After that, I was able to hand people a business card instead of having my coffee held hostage. What started as an outfit of the day blog, quickly grew into a styling business as well as a platform for body positivity and self-love.

I think what a lot of people don’t realize is that a large part of Windy City Wardrobe is, not just through photos but also through styling sessions, helping plus size women past barriers in fashion. What I realized was that I couldn’t help women figure out the wardrobe if I couldn’t help them unpack all of the baggage they had about looking how they are. It doesn’t matter how nice your new clothes are if you don’t have any confidence to put inside them.

Money is a powerful thing so it’s important to take the time to ensure you’re upholding your own personal values.
— Dasha Guyton

What’s broken in the blogging industry and what are you doing to change it?

There aren't many "organic" bloggers left. By that, I mean people who blog for the sake of blogging and giving people honest answers to everyday life problems. These days, people start blogging because they want in on the perks or they're simply looking for attention and fame. I do my part by keeping it real. I turn down 90% of the offers brands make me because I take my influence seriously and because of that I won't ever make my blog a source of full-time income. I don't think it's possible to stay on brand and give people the expertise in your niche if you're trying to be everything to everybody and pay your bills.

I don’t edit my photos. I don’t use photoshop. If this is what I’m looking like today, this is just what I look like.

So, in addition to Windy City Wardrobe, you run Feminist Speakeasy. What motivated you to launch this brand and how has that experience been different from launching Windy City Wardrobe?

It kind of started with the growth of the self-love and body positivity topics. It was beginning to be too much for Windy City Wardrobe to handle.

With such broad topics, it became necessary to launch another brand and that’s when Feminist Speakeasy was launched. Here, I get to use my point of view as a multi-racial lesbian and intersectional feminist to curate and create conversation-starting pins, shirts, jewelry, and events. With Windy City Wardrobe I took a photo and pushed a few buttons and bam I had a blog, but launching Feminist Speakeasy was a lot harder because it wasn't on a whim. It's an idea I thought about for a year then strategized to bring to life for another year.

You can’t just keep giving everybody all of you for free. I have lots of opportunities to make money with Windy City Wardrobe, but it wasn’t what I wanted to turn it into. So I purposefully left Windy City Wardrobe as my hobby, my project, something I do, but not trying to make a profit. Whereas Feminist Speakeasy was and still is about profit as well as community.

Although this idea was already ruminating, what really lit a fire under my ass was honestly just Donald Trump winning the presidency. I have never been more devastated and it kind of changed how I do things. It was like, okay, not later, now. Because apparently things are worse than I thought they were.

What do you love most about your customers?

This business gives me just as much back as I give to it and there's so much I love, but what I love most is how deeply customers connect with each other, with me, and the products.

What I do notice, and I was happy when I started to see it happen, is that people often purchase the same product twice. They’ll keep one for themselves and give one to a friend. So when people started to do that, I knew that it was working. Because the whole point is not just for you to have the little things and for me to make the money off of it, it’s to start the conversations that we aren’t having. And to have them in real life with people we care about and not just random people on the internet who pissed you off.

There are a lot of large companies capitalizing on feminism in this moment to sell products. What’s your perspective on this trend and how can consumers support businesses that truly share their feminist values?

The internet can be a noisy place, especially for the continuing conversation about what Feminism really means and who is included in the dialogue. The idea that culture vultures will drown out inclusive Feminists keeps me motivated to do my part in advancing the movement and bridging the wage gap. My advice to consumers? Do your homework. It's easy to say what you stand for, but the proof is in their actions. Are their campaigns offensive? Do they support the feminist movement year round or conveniently around International Women's Day and other holidays? Do they employ women from diverse backgrounds? Money is a powerful thing so it's important to take the time to ensure you're upholding your own personal values.

I’m partnering with other women-owned businesses that are local, and that feels great, and that helps grow our local community. Because we’re all trying to do the same thing. We all believe in equality, and we’re all looking for ways to make things better instead of just letting these large corporations profit off of the movement that we’re all doing the hard work for.


Interview edited for clarity and brevity.

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