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Conversations with Jennifer Giles

Today we’d like to introduce you to Jennifer Giles.

Hi Jennifer, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
Absolutely! I’ve always been interested in fashion since I was younger. I really never knew you could get paid to style everyday people. Sure, I knew celebrities had access to things like that, and I never really believed it could be a reality of mine – until 2014 when I was on Instagram and somehow I found celebrity stylist Shun Melson. I started following her and learned that she had grown her own personal styling business, and at that point I knew that my dream could definitely become a reality. I didn’t know how or when, but I knew I had to make it happen.

Fast forward to October of 2017, I started Sassy & Classy Styles. I would start off with dressing my close friends, helping them pack for trips, advising them what to wear, etc. Slowly, I started to add different services based on the work I had done with my friends. I added closet organization, which is surprisingly my favorite business task. I had always had a passion for helping others, and with the growth of social media and women feeling like they needed to conform to “the Instagram model,” my t-shirt line came into fruition. My first shirt was “Match my Confidence,” which is a simple yet loud statement, in my opinion. I want these women to indeed Match my Confidence and know that they look great just the way they are! I truly believe there is inner confidence in everyone and that if they dig deep enough, they can tap into it and unleash the powerful woman they are all meant to become. My close friends joke with me often about how I unapologetically live my life and I put that same energy into my business. My second shirt is called “Your Opinion,” which reads, “Your Opinion doesn’t FEED or FINANCE me.” Basically meaning I really don’t care what you have to say, I’m going to do me and do it well!

In 2019, I packed up my life and moved to Atlanta, but HQ is still in Florissant. I still have clients at home and I come home quite often for business-related things. During the pandemic, I knew I wanted to grow my business, but I didn’t know-how. I already have services and shirts, so I decided to add jewelry to the mix. That did great, so now I am gearing towards an online-based boutique while still offering my stylist services. I have a blog on my website, which I provide helpful styling hacks, shopping tips, etc.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
I’m going to be completely honest. Starting a business isn’t hard, but you definitely need to have a plan in place. I pretty much learned things as I went. At first, I thought, well, I have an LLC now, so this should be easy. No. That’s not the case. There’s a lot of research that needs to be done on your end. I am still learning to this day. I started off making so many mistakes with pricing, shorting myself, not knowing my worth when it came to my business. I would get so disappointed when some of the people I would consider friends wouldn’t support me. You learn a lot when you own a business about support. I’ve also wasted so much money.

One particular story I always tell one of my best friends is great, so I’ll share it here. She has been one of my biggest supporters when it comes to my shirt line. I would get the payment for the shirt, which would be $20. I would take that same $20 and go get the shirt made – actually, it would be around $25, so I would lose money! LOL! I came and got so many shirts made, the employees were like, hey, so why don’t you do a bulk order, that way you could save money. I’m just glad someone told me! I had no clue about shirts, I just knew I wanted to do them at the time! I am a big advocate now for gaining education on your business, specifically in your niche, so you can learn what to do and what not to do from those who have been there before.

Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
My business is an online boutique. I sell jewelry, my t-shirt brand, and beauty headbands. I also offer personal styling services, virtual consultations, packing assistance, and my all-time favorite, closet organization. I’ve done a lot of closets and for me, it’s super therapeutic. What you see as an overwhelming task, I see it as an art project. I would say closets are my specialty. I am proud of all my closet work. I enjoy helping women gain their confidence, but it’s something about organizing a closet that gives me joy.

What sets me apart from others is that I spend a lot of time with my client when it comes to the organizing stage. Most times, the client isn’t there, but I want them to be completely aware of what’s going on when I’m in a closet. You’d be surprised at how hard it is for people to get rid of clothing that’s been sitting in their closet for years, never being worn. I also like to donate the clothes that we get rid of, as long as they are in good condition. I’m always looking for suggestions of places that need gently used clothing to help the less fortunate.

Who else deserves credit in your story?
Do you know how people say “It takes a village”? Well, that’s definitely true when it comes to a business and owning a business. There are so many people who have helped me over the past four years. My close friends, Danielle and Adeesha, always support me when it comes to purchasing merchandise. They also tell others about my business or my website and give me different ideas I can implement. Danielle has let me organize her closet and always calls me for style help. My mom is my biggest cheerleader as well, she’s always supported my dreams and didn’t think my business was too crazy or out of reach. I’ve taken business classes and I want to send a special shout out to all the business teachers I’ve encountered over the years – I definitely couldn’t have done it without the instruction I’ve received.


  • Jewelry anywhere from $3-15
  • T-Shirts $15-$20
  • Free Shipping over $20

Contact Info:

Image Credits

Main Picture, JaiKal Photos, Athens GA

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