The philosophy of HEYDAY Boutique simply put is “HEYDAY exists to provide joy, confidence and inspiration to our customers and team while making people’s lives better through our happy, playful aesthetic and incredible customer service experience where we connect and engage in meaningful, uplifting and real conversations.” Words that Jennifer Little and her husband, Ryan, have lived by and that their clients have experienced since they created the foundation of HEYDAY in 2015. This dedication to their new and current customer base has earned HEYDAY a reputation as a warm place to shop their amazing selection of high-quality curated offerings of women’s apparel, shoes, accessories and jewelry, as well as home and gift options. “We’ve also had so many customers ask us the question, ‘When are you going to come to Denver?’” said Jennifer. So, it’s no wonder their relocation serves well for their happy Denver clients and the new ones alike, who will experience the laid back, warm, charming and happy space that Jennifer and Ryan have made. HEYDAY is proving to be the go-to for Denver clients looking for one-of-a-kind offerings in woman’s apparel and gifts for your home. 303 Magazine sat down with Jennifer to talk about her journey in retail and her move to Denver.

303 Magazine: Why did you make the move to Denver and what are you looking forward to with this move?

Jennifer Little: Ryan and I were shopping the Fort Collins real estate market for additional ways to grow, but we were not finding the right fit. One of our amazing customers, Ashley Stiles, who worked for McWhinney at the time, reached out to see if we had ever considered a location in Denver. We’ve also had so many customers ask us the question, “when are you going to come to Denver?” and the timing and location made perfect sense. The Dairy Block is a community within LoDo, and we love being a part of the downtown life of Denver.

 303: What can people expect when stepping into HEYDAY and is there any difference between the Fort Collins store and the Denver store?

JL: Customers will experience a fun, fresh, playful, laid-back spot filled with a curated selection of goods for themselves and others. We offer a very welcoming vibe that instills confidence, joy and inspiration while certainly receiving an incredible customer experience. Although very similar, our stores have a different feel to them based on the history and location of the spaces. Our Fort Collins Jessup Farm location was once a 100-year-old farmstead while Dairy Block was home to Windsor Dairy and is nestled in the heart of LoDo and offers a more clean, modern, urban feel. At both shops, we offer a number of the same brands from clothing, shoes and gifts to apothecary and home, while incorporating unique pieces specific to each location.

303: What makes HEYDAY unique from other boutiques and why should people be drawn to shop at HEYDAY?

JL: We want everyone to feel welcomed, inspired and full of joy when they walk into HEYDAY. We are creating the best experience possible while engaging in meaningful conversations and finding the right items for each person. Our shop is curated to provide an engaging experience of sights, sounds and feelings. It’s important that our customers know they can pop in for a moment or stay all day. You will spend time gaining inspiration and building a community when coming to HEYDAY.

303: Growing up, did you always have an interest in working in fashion?

JL: I’ve always had an eye for design and style — something that I received from my grandmother. She was a master at creating a beautiful space on a budget long before it was a trend. My background is actually interior design and photography, and having been in those fields for a number of years, I was convinced that I could bring my passion to life through a boutique curated for those looking to be inspired. Regardless of medium, I love to implement color, texture and pattern in a fresh, clean, playful and unexpected way.

303: What inspires you when stocking pieces for HEYDAY?

JL: Happiness and joy inspire me. Great branding and great stories inspire me too. I depend a lot on how something makes me feel. I love a mix of high and low. It’s not always the most expensive item that you need, but sometimes the most expensive item is the most amazing item. It’s very confusing.

What I always strive for are products that are phenomenal and joy-filled no matter the price. Our customers love the mix of items in HEYDAY too because they take home items from all price points often in the very same purchase. It’s always about finding great unexpected items and juxtaposition. I’m always asking these questions: “Will our customers love it? Will it make them happy? Does it make me happy? Is it beautiful? Is it comfortable? Can someone wear this to express themselves? Is it different than what we currently have in the shop? Is it fun, playful, classic?” I am constantly observing things around me, looking for inspiration, paying attention to things that compare and contrast, looking at how people live and interact. Observe, observe, observe.

303: What do you attribute to the success and growth of HEYDAY?

JL: I attribute hard work, a magnificent team, incredible brands and welcoming, genuine customer interactions to the success and growth of HEYDAY. We spend a lot of time listening to our customers. We are listening through personal requests, what they buy, what they don’t buy, always listening. HEYDAY has always been an evolution. I truly believe HEYDAY has been evolving since I began paying attention to the world around me as a little girl in South Georgia. It will continue to be such. You have to be firm in who you are, what you do and why you do it, but you have to be flexible in how you make it happen.

303: If you could go back and tell yourself one thing before starting your career, what would it be?

JL: Walk through open doors. Opportunities are all around us. Be willing to seize them. Combat fear with gratitude.

303: Who have been your biggest mentors within this industry and what is the best advice they have ever given you?

JL: Jade O’Connor (Metal + Petal Design Firm), Allyson Conklin (Allyson Conklin Public Relations), Susan Sigman (Semester at Sea), Kyle Sheppard (my mom) and Ryan Little (my husband and business partner) have all been my mentors guiding me, encouraging me and holding me accountable every single step of the way. The amount of insight and advice these amazing people have given me over the years is countless, and each person provides a different perspective and strength. I am forever grateful, and we have all grown together.

303: What is a valuable thing you have learned while being a boutique owner for all these years?

JL: Surround yourself with an incredible team. Do everything that you can to take care of them, who will, in turn, do anything to ensure that our customers receive the same incredible service time and time again. I can’t be in each store every day and work with every single customer, but I can hire the best people possible who share my vision. We have a great team who wants to make every customer who walks into our stores feel special, joyful and inspired.

303: What are the challenges/setbacks with owning your boutique that you have experienced and how did you overcome them?

JL: Starting out, the time and energy it took to get things off the ground were extremely taxing. For the first six months, I was the only one in the store on a full-time basis, seven days per week. I had, and still have, an incredible support network at home, and I’ve built a great team. This allows me to be able to spend more time on the vision and direction of our stores while allowing me the opportunity to focus on curating the best possible HEYDAY.

303: What advice would you give to young women hoping to one day follow in your footsteps? Where do they begin?

JL: You need to be passionate about what you want to do. You need to truly understand why you are doing what you do. Most importantly, however, is you need to be willing to work very hard — harder than you can ever imagine possible. Find fellow business owners who are in the trenches too doing the work and talk to them often. Watch how they work. Pay attention to how they inspire their team. You have to care about your team and be willing to invest in their growth. You must be willing to get the smallest things right in order to make the big picture beautiful. Be original. If you have the courage and gumption to figure it out, you will be just fine.

 303: How will Denver impact the growth of HEYDAY and what more can be done to enhance the “shop local” aspect of the fashion scene within the city?

JL: We are excited to address a need and a request from our current customers who wanted to us to be in Denver, while at the same time, bringing an incredible option for those who have yet to experience what our stores have to offer. Denver is booming. That is certainly apparent. LoDo is seeing incredible growth both from a local and national perspective. Downtown has had a great history over the last couple of decades as a destination for dining, entertainment and other activities. Now we are seeing an opportunity to serve the area as a go-to local, neighborhood boutique. We are growing but want to maintain that “local” feel. We are honored to be a part of the Dairy Block which is complemented with both local and national retailers.

303: What advice would you give to anybody who wants to open up or just opened up a boutique and is hoping to make it in the industry?

JL: Work hard and believe in what you’re doing and why you’re doing it. Don’t be afraid to make changes when necessary and don’t be afraid to take those calculated risks. Go your own way and provide something unique.

 Photography by Karson Hallaway.