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Conversations with the Inspiring Dasha Guyton

Today we’d like to introduce you to Dasha Guyton.

Thanks for sharing your story with us Dasha. So, let’s start at the beginning and we can move on from there.
Five 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 Chik-Fil-A but the barista’s 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. Now I’m 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.

Eventually, I started modeling for brands, writing for print and online publications, and speaking on panels about blogging, entrepreneurship, and feminism. 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 content.

Has it been a smooth road?
The only obstacle I’ve had is myself because I have a bad habit of spreading myself too thin. So, my advice to you is learn to say no more often than you say yes. You must protect your brand by aligning only with companies and individuals that you think will represent you and your brand in a positive way. But don’t limit yourself to working with other bloggers and brands, think bigger. Join local blogging, writing, and small business groups as you look for photographers, videographers, makeup artists, performers, caterers, event planners, and public relation professionals to add to your tribe.

So let’s switch gears a bit and go into the fact that you I have two brand stories, Feminist Speakeasy and Windy City Wardrobe. Tell us more about the business.
There are tons of people you can go to for wardrobe styling, but they don’t have my background in self-love and body positivity. Most stylists work with brands and sample size models so they lack empathy and experience dressing larger bodies. I’m known for helping people with special events and transitions in life that require a new wardrobe.

Also, I run one of many feminist gift shops, but mine globally helps bridge the wage gap plus it’s intersectional. Every purchase in my shop support multiple women owned businesses. At Feminist Speakeasy, we believe that real change can only happen when we all come together to dismantle racism, sexism, homophobia, xenophobia, transphobia, ableism, and classism. The products I offer and conversations I lead on our Facebook Page are indicative of the spirit of inclusion and people want to be part of that resisterhood.

For good reason, society often focuses more on the problems rather than the opportunities that exist, because the problems need to be solved. However, we’d probably also benefit from looking for and recognizing the opportunities that women are better positioned to capitalize on. Have you discovered such opportunities?
As long as women aren’t treated fairly and paid equally we will continue to create new economies. We see proof of that in blogging, brand ambassadorships, and influencer work. Women have always been good at influencing others people’s purchases and habits, now we’re just getting paid for it.  Women are well positioned for the rapidly changing terrain of the internet because whatever a woman has become known for in her social circle she can now monetize the skill through social media.


  • All feminist gifts are below $40

Contact Info:

Image Credit:

Michelle Cox Photo,  Levine-Moore Photo, Feminist Speskeasy

Getting in touch: VoyageChicago is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

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