Discovering the Power of Quality Over Quantity

Ebby Antigua of Ebby Magazine interviewed Diana for their September print issue. Below is a recap of their conversation.Diana LoMonaco has always had a passion for fashion. She has dedicated her career to creating stylish, affordable, and timeless clothing. After years of designing ad campaigns for Macy’s, Diana decided to take it one step further and start her own fashion blog. As she talked to fellow fashion lovers, it became clear that many women were overwhelmed by the choices and accumulation of clothing in their wardrobes. With the vision to create a brand that encouraged quality over quantity, Diana founded Classic Six to help women build an accesible, fashionable, and practical wardrobe. Through her expertise and knowledge, she helps busy women create versatile wardrobes that allow them to express their sense of style without breaking the bank. By providing timeless pieces made with quality fabrics, Diana has created an easy way for anyone to curate a personal style. Learn more about Diana’s inspiring journey and the unique vision of Classic Six.

What inspired you to start Classic Six? It was a moment of my own overwhelm that planted the seed. I was endlessly shopping and buying clothes to use in styling this blog that I was working on and realized I had become the walking cliche of “a closet full of clothes and nothing to wear.” In those moments of overwhelm, I said to myself, ‘I can’t be the only one feeling this over­ whelm with the amount in my closet and the amount of choice in stores.’ I often talk about the experiment I did with myself at that time.

I basically created my own little capsule ward­ robe. I chose a handful of my favorite pieces that I would always reach for, took them out of my closet, and hung them on a rolling rack. Some were vintage, some I had designed for myself over the years, and some were just those favorite classic pieces I bought years earlier and could never find again. Everything else I shoved in my closet, closed the doors, and didn’t look at them for months. I wanted to see how I felt with a smaller wardrobe. Was it easier to get dressed? Was I forced to become more creative in my styling because I had less? ALL YES. And that is when I knew I had an idea.

How did you balance running your graphic design business with starting Classic Six? I wouldn’t say it was easy, but like you mentioned, I was always one to have a side hustle, and Classic Six came about when I needed a new one. I think my creative energy needs the “other project.” My graphic design business started as a side hustle to my full­-time job. When I left the corporate world to work on my graphic design firm full-­time, I needed a new side hustle. Enter the blog. When the blog became something I didn’t find joy in doing, I sat with my free time for a bit and then decided I was ready for another side gig. Classic Six became that. It was my new client while I worked on graphic design projects for other clients. It fueled my creativity in ways I never even expected. It was only until last year that I closed the doors on Diana LoMonaco Design, andClassic Six became the priority. Now that I am not running two businesses simultaneously, opening the store is the new side hustle. Maybe I need to find a better word because I’m thinking hustle doesn’t quite work for any of these scenarios. I love having something exciting to think about and plan for on the side of my main gig. What can we call that? Passion Project works.

What do you believe is the most important quality for a successful entrepreneur? I am still learning every day, so I like to preface this question with that, but at this point in my entrepreneurship, I would say flexibility. I think you have to be comfortable with the idea of taking risks and know before you jump in that nothing ever goes 100% as planned. Be ready to pivot at a moment’s notice. A rollercoaster is the best way to describe it. The ups and downs are never­ ending. Being an entrepreneur allows you the creative freedom you never knew was possible, but also levels of stress that require constant management. Also, organization—at least for me. My work revolves around a to­-do list that I have organized by year, month, week, day, hour, and sometimes minutes. It is ever-changing, but it allows me to compartmentalize work and life. At the end of the day, whatever needs to be done is taken out of my brain and put on this list; I don’t have to think about it when I turn off work mode. I swear my to­-do list is responsible for my sanity.

How do you ensure that the pieces in your collection are of high quality and thoughtfully designed? Thoughtful design is the easy part. I live and breathe it. It is what makes me tick. Quality is the hard part and also the most important thing to me with regard to this brand, so it is where the biggest stressors come into play because I am not fully in control. We have hundreds of people working on the construction of our garments in our factory, so I have to trust that I’ve put the right players in place to ensure the specs we have created are followed. We recently had an issue with our Katharine blazer where the buttons were not secured tight enough and customers were losing them. It’s moments like these that I am reminded that I am creating a business bigger than me. I try not to get myself into a tizzy because, at the end of the day, we are not curing cancer here. Instead, my immediate response is to spring into action. We had a new button machine in the factory within months. I had a tailor come into the warehouse to mend every in­-stock blazer one by one. For every email we got from a customer, new buttons were sent with a discount code for their next purchase, or a replacement was offered. I want to make sure our customers know that quality is a priority. We are still a relatively new brand working to make it the best possible, and I am constantly looking towards getting it to a place where we (I) have to worry less. That means making sure we have the right processes and people in place to produce at larger scales without sacrificing the quality and customer standards the brand is built on. It takes being in control but also letting go of control. I am still working on that. It is not easy for me.

What were the main obstacles you faced while leaving a corporate job to launch your own business? For me, it was the guilt factor. When you have your own business, you have a flexible schedule, which is both a blessing and a curse. Granted, I started my first business in 2011, so the idea of a flexible schedule wasn’t even a thing then. I was, like many people at that time, conditioned to a structure of 9 to 5, 3 weeks of vacation, three sick days, etc. When I started my first business, I found myself able to leave my desk at 11 a.m. to go to the gym. I could take a 2­hour lunch if I worked later at night. I could take time off to travel and only check my computer in the morning for anything pressing. It felt like freedom, but also like I was playing hooky. I felt guilty when I was doing anything else but working. It took me a while to get out of that headspace and adapt to a new life where I made my own schedule and was responsible for getting everything I needed done according to my own timeline. Now I look at time off as a gift I deserve and less of a guilty pleasure. Work hard, play hard, right?

What have been some of the biggest challenges you’ve faced while running your own business? I think the supply chain crisis during the pande­mic was one of the biggest challenges for me. I am a planner, so like I said above, I like to have a plan in place before I share mostly anything. Looking back, even though we had to pivot, I am so thankful for that plan. I revealed our products and launched a pre-sale for our mailing list right before the start of the pandemic, thinking our production run was going to arrive just in time for our February 2020 launch. I found out in January that my factory in China had shut down indefinitely. I had all of these people waiting for the product they bought and no way to get it to them. I am so thankful to all of our first ­time customers for their patience and understanding. I often say those are the people who built this brand—the sales we made in that original pre-sale paid for our first production run. To make a long story short, I decided to fully launch the brand without any inventory in stock. I had all of this amazing content ready. I was eager to have more than my mailing list learn about the brand. So on April 1, 2020, a time when people were glued to their social media, I had the opportunity to start telling our story. By the time our product came out in July, people were excited and ready to shop.

How has your approach to fashion changed since starting Classic Six? Before I started Classic Six, I was an avid fast­ fashion shopper. The blog was all about high and low styling. I loved a bargain and still do. You can often find me in a thrift store, searching for gems. Though, since starting Classic Six, my focus has become more on being conscious of how I shop. I know that buying quality clothing is a privilege, but I also know now more than ever that setting the foundation of your wardrobe with a handful of quality pieces is setting yourself up for success. And I don’t just mean quality in construction. I mean quality in design. Is it thoughtful? Can you style it in lots of ways? Is it timeless enough that you won’t want to pass it on in a year? I take these moments now, before I buy something, to think about how I will wear it. Will this piece work with the classic foundation I have set? I say all the time that buying less and being more conscious about what we buy is really the only sustainable option.

What did you learn from your experience launching Classic Six? Where do I begin!? LOL I think the biggest thing I learned about myself is that I can do anything I put my mind to. I did not go to school for this, but I wanted it and made it happen. I’m praying now that I can keep it going! There are so many resources out there today that we can use to our advantage when starting a business. I was on YouTube every day, watching anything I could on the business of fashion; I joined entrepreneurial groups of other people starting fashion brands; I read article after article, all right at my fingertips because of the internet. It was all free information. I would tell any entrepreneur to never doubt their abilities. The “but you never went to school for that” shouldn’t even be a narrative. We are so lucky to be living at a time when resources are plentiful. You can make anything happen if you have the passion and the drive.

What was the biggest obstacle you faced when trying to collaborate with brands? We did a lot of collaborating with accessory brands early on. Styling is a huge part of our DNA. We want to show the customer endless ways to wear one piece for different times of year and different occasions, and accessories and shoes are important. Our uptown girl is wearing the white Donna very differently from our downtown girl. How can we show all the ways that classics transcend style types? We are not just selling the pieces; we are selling our styling of them, so the customer walks away with not only a great piece of clothing but also the styling ideas so they don’t wind up sitting in her closet, never worn. I digress. The biggest obstacle to this sort of collaboration was the bandwidth. The brand outreach was a full­-time job in itself. The initial pitch includes choosing from available products, coordinating the products being sent, the follow­up, the shoot­ing specifics, and the packing and shipping to send the product back. I would need to hire a team to ever go that route again. It made plann­ing our shoots extremely hectic. Now that I find small brands I love, I buy the pieces for the shoots and reach out to the brand after we have these amazing photos of their product. If they want to share, they can, and they most often do!

What are your future plans for Classic Six? Oh gosh. I have BIG plans that go beyond even fashion. I think consumers want someone to cut through the clutter for them in so many categories because the options available to us are truly over­ whelming. They want to hear, “We’ve narrowed it down for you; we did the research; we designed what we know you are going to want; you don’t have to spend hours of your life searching; here is what you should buy, and here is why.

How do you feed your body, soul, and mind? Pilates and acupuncture, both of which I have yet to do since moving, are things I need to get back into asap. I notice the difference when I don’t make it a priority. This goes back to what I said earlier about the stress of business requir­ing constant management. Self­ care needs to be a way of life. Add it to your payroll.

Have you found your purpose? If so, what is your purpose? I don’t think so. It’s still a journey for me. I do think everything I do is leading me to finding it though, so it is exciting to think about.

What kinds of things are luxurious for your soul? Catching up with old friends, exploring the world, the beach, live music, candles, clean crisp sheets, good food, a glass of wine, a hot hot shower…if I sat here for longer I could probably make a list a mile long.

You can learn more or shop at and on instagram @classic.six