We were lucky to catch up with Sydney Underwood recently and have shared our conversation below.

Hi Sydney, thanks for joining us today. Let’s talk legacy – what sort of legacy do you hope to build?

Our mission is to make people feel inspired & empowered. We started this business because we wanted to connect to others through self love, women empowerment, mental health awareness & body positivity. This is why we had the sayings that we have on our clothing, “More self love babygirl,” “Self love club,” “She is evolving.” When people put on our clothes they feel good. They feel seen. They feel loved. We also use affirmations instead of standard size names, to really emphasize that we are more than just a size. We are Capable, Deserving, Valuable, Enough, Worthy. We feel like the world has been so delicate over the last couple years. We’ve lost a lot of loved ones. people are struggling financially, the mental health of the general population has been incredibly fragile – it’s important to love one another & ourselves. It’s important to get these reminders as often as we can. We hope that what we’re doing feels like a hug. We just want people to remember how outstandingly needed they are here.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

We are a two woman business! We are two best friends who met playing volleyball in college & have been pretty much inseparable ever since. We have always been into health, fitness, & wellness which is where this whole idea started. We actually started by making digital content promoting self love, body positivity, mental health awareness & more via instagram. Eventually people started asking us for merch because they wanted to support us further — that’s when Boss Lady Apparel was born. We knew we were totally into the idea of creating apparel, but it was necessary for us to continue pushing our values through our clothing line. That’s when we came up with the idea to use affirmations instead of standard size names. That in itself, is by far is one of the coolest & most unique things about our brand. We also take a lot of pride in the fact that we are an inclusive brand, making this a safe space for all. We also design all our of pieces. We’ve been able to connect to so many people through this conversation of self love. So much so, we realized we have A TON to say about it, Which is why we also started our very own podcast called, Come As You Are. We talk everything self love, mental health tips, wellness tricks, body positivity and more. It’s been a great additional branch for us to connect with our community. We are big on community, as they’ve given us an incredible amount of support. We love to give back, we donate a portion of our proceeds to various local establishments that give back to women.
This brand really practices what we preach & we are very proud of that.

Can you tell us the story behind how you met your business partner?

Sydney here – so I am originally from Spokane, Wa. I ended up going to school at Whittier College to play volleyball. Corie, who is from Oregon City, Oregon, also ended up going to Whittier college to play volleyball. I will never forget, driving from Washington to California with my dad to retreat before school started to what was called “hell week” for our pre season volleyball camp. After the first day, Corie’s and I’s friendship was completely solidified. We clicked instantly. Literally became best friends within days. We have been through so many things together – we’ve lived together, went through the struggles of studying away from home together, did the entire college experience together. After college, I ended up graduating a year early and took a job in Walla Walla, Wa while Corie finished her last year of school. I think I had to have flown down to visit her at least 5 times that school year – no joke. She ended up taking a job in California after she graduated, when I actually got transferred to Portland, OR. As you can guess, we still remained best friends during that year as well. Well Corie decided to fly home (since she’s originally from OR) for the holidays in 2019. I will never forget, I went to pick her up from the airport and we had a whole week of activities planned for Christmas and New Years, we were walking through the parking garage and she yelled my name so I looked back all concerned, she had her phone out and was recording me. She said, “Are you ready for me to move back?” I was confused at first, since her and I had never lived in Portland at the same time. Then it hit me. She was moving back home to Portland.

The thing about Corie and I’s friendship, is every single detail about it has been God’s timing. It’s so evident he wanted us to be best friends. Anyways, I’m sure the story is much more heart touching to me, but we really are incredibly close, I’m incredibly thankful for her and I feel so lucky our friendship continues to get only better ever since we became business partners.  

How’d you build such a strong reputation within your market?

Not taking shortcuts. Your brand IS your business. We have, and still do, put our branding above anything else. We think about our brand before we do anything – collaborations, marketing, email campaigns. And we make sure that everything we participate in or put out is in alignment with us genuinely. In addition to this, being in this industry, I’ve learned you don’t have to do good business to be successful, but good business will always go the distance. We just try to be the best we can in every situation. We uphold the same customer service/return/exchange policy as Nordstrom, for example. Which is pretty crazy for a small business, but that’s the standard we want to set for our community. We look at this brand as though we are serving the community we’ve built, not just selling clothes to people. Business is always personal.

Contact Info:

• Website: bossyladyfitt.com
• Instagram: @bossladyapparel_
• Other: TikTok: @bossladyapparel Podcast: Come As You Are

Image Credits
Image Credits: Visuals By Vary Studio Credits: Cobalt Studios