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Career Corner: Founder of Dress Downs, Simone Magee

We all have to make a living—why not do it while #livingLIVELY? Welcome to Career Corner, where we interview badass women blazing trails across all types of industries. Here, we chat about their daily hustle, how they found success, and why they love what they do. Come for the career advice; stay for the inspiration.

Today, we chat with Simone Magee, founder of Dress Downs.


What is your business and how did you come up with the idea?

Dress Downs is a fashion solution I created after having an embarrassing Marilyn moment while walking in downtown Chicago a few years ago.

As an entrepreneur, what do people assume you do?

People always assume I’m in the tech field, since that field is highlighted more when it comes to innovation and entrepreneurship. It's funny because I’m the least "techy" person, #teamadroid.

Now, tell us what you actually do.

Simply put, I work all day proving a market. Whether that’s through online efforts, at events, or through emails. It’s hard to remember a time before Spanx or Fashion Tape, but someone had to tell you they were solving these common fashion mishaps before they became a staple in your wardrobe. 

What does a normal day look like?

I wake up at 6am to head to the gym first before diving into my to-do list. My list can range from creating content, shipping international orders, and making sure the backend of different platforms is running smoothly. After that I answer and send a few emails. I landed my first national retail deal so that process can be tedious for new vendors and it can be a lot of back and forth. By the afternoon, I’m on the phone with my manufacturer making sure everything is still on schedule and that we’re further improving the product.

What was it like starting your own business and what did it take to get here?

I didn’t personally know any women or men my age who invented their own product or service, so I had to learn as I was going and from reading. There’s no perfect roadmap for being an entrepreneur so it’s been an uphill journey. It’s taken a lot of sacrifice and pure determination.  

What sort of skills or experience do you need in order to succeed in your role? When and how did you get those skills?

You must learn how to handle rejection or criticism well. “No” is and always will be a part of any entrepreneur’s journey. It’s impossible to avoid. For me, that came with time. In the beginning, when someone told me “No” it would knock me down for a bit, but now I just shrug and keep going. 

What’s your favorite thing about your job?

No day is ever the same.

What’s your least favorite thing about your job?

It’s almost as bad as mansplaining, but having to read a man’s comment on a product they would never use. Or worse, them saying I’m ruining something they enjoy seeing happen to women. Although I will say, the majority understand the issue for women.

How has your job changed over time?

I’ve completely bootstrapped Dress Downs so I have always done everything when it relates to the company. From the manufacturing process all the way to customer service, and that hasn’t changed, but now I have one bad ass intern who plans out social media. It has been such a huge relief to know that on those tough days when I’m tapped out mentally on the creative side, she has it covered.

How did your expectations of being an entrepreneur differ from reality?

The only expectation I had as an entrepreneur was the freedom that would come with it. In some ways it has been better than what I could have imagined. I make my own schedule, can never be micromanaged, and can set the bar as high as I want. But, that freedom came with a cost. The financial security I gave up when I quit my full-time job meant I had to give up things I didn’t realize were luxuries before.

What’s the best piece of advice you’ve ever received?

 Failure is only final if you allow it to be.

What are some of the challenges you’ve faced, either in your current role or throughout your career? How did you work through them?

I always felt underestimated by the work I was or wasn’t given in my previous roles. I knew my worth (and added tax) so it was more than frustrating. Especially since I worked in environments that did not encourage employees to speak up. Me working through that was quitting and moving on to something better. For me, that was Dress Downs. There are companies out there who will see your worth and potential. You shouldn’t be miserable at the place you spend much of your time. I hope I get to create the company that I always wanted to work for.

Was there one defining moment you can point to that put you on the path you’re on?

I used to help create children’s promotional products for Kellogg’s, Burger King, and Girl Scouts. We took our ideas from paper and made them into physical objects. I didn’t know it at the time, but it was the final piece I needed to create Dress Downs.

What’s one piece of advice to give to people who are interested in entrepreneurship?

You’re going to have to learn as you go so don’t worry if you don’t immediately have the answer for everything. 


Fave LIVELY pieces?

Being an entrepreneur, I get to work from home a lot, so when I do have to get up and actually wear a bra, the only one I want to wear is my soft pink Long-Lined lace Bralette. It feels as if I’m wearing nothing. When I’m dressing up though, it’s The Lace Strapless. That’s the first strapless bra I’ve ever worn that stays in place. 

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