It’s Derby season! One of the best things about the Derby is the fashion—it’s preppy, Southern-inspired, just a bit loud, and a whole lot of fun. Two of our customers, Heath and Julie, lean on their stylist’s expertise to create their looks from scratch every year. The most impressive thing is that they travel over 400 miles from western Kentucky to our Chicago Clubhouse to get styled! Why go through all that trouble? Because when you throw a Derby party worthy of the winner’s circle, you have to look great doing it. Read more about Heath and Julie’s Derby party, and how their relationship with their stylist is what makes the whole process truly special.
What made you start coming to Chicago for Clubhouse appointments?
Heath: Our first trip to the Clubhouse was in 2014. Julie and I were looking for an after-tax-season getaway and decided to come to Chicago and visit the Clubhouse. I had been a customer for about a year and really enjoyed the service… Back then, Trunk Club only offered services for men, [but] as they added services for women and Julie became a customer, our Clubhouse visits have become an annual tradition. Given the timing so close to the Kentucky Derby, seeking out our Derby party outfits has become a major part of our Clubhouse visits.
What’s your favorite thing about shopping at a Clubhouse? Why?
Julie: I don’t have to shop! I have always been a buyer, never good at shopping. I love getting the chance to try on things I would have never picked for myself. We also look forward to seeing our “Trunk Club friends.”
Heath: When I shop for myself, I often feel overwhelmed with all the choices that I end up losing interest or motivation… Visiting the Clubhouse takes all that away. My stylist has already done the hard part and selected specific items for me. Going to the Clubhouse feels more like hanging out with friends than it does shopping. The bourbons that seem to magically arrive are also an especially nice touch.
Tell us about your relationship with your stylist.
Julie: [My stylist] felt a lot like family that lived out of town. She’s styled us for some of our favorite events, and we always wanted to let her know when we had on our favorite pieces.
Heath: I’ve been extremely fortunate to have worked with two amazing stylists. My original stylist quickly understood and adopted my perception of my style while gently nudging me out of my comfort zone… For me, the most important thing is the confidence I have in their sincere desire to help make me look my best. I completely and without question trust their opinions about my style, the clothes I choose, and how things should fit. If they say I look good in something, I trust them, and perhaps more importantly, if they say something doesn’t work for me, I trust that too.
How has your Trunk Club stylist become a fixture in your life?
Our stylists have helped us with outfits for so many fun and memorable events. Whether it be our annual Derby party, a vacation, a wedding, or an important work or community event, they have never failed to help us feel like we look our best. By extension, they’ve become a part of each of the memories made at those events. It’s almost like they are there with us. When we get compliments on what we’re wearing, we think about them and want to share it with them.
What details are must-haves in a Derby outfit?
Julie: The hat is the traditional answer, and that holds true for our house party as well. But it’s more about the way what we are wearing makes us feel. It’s the dress, the shoes, the hat, and feeling like I look my very best. Trunk Club and our visit here each spring helps make that happen for us.
Heath: I’m a hat guy, so that’s a must-have for my Derby outfit. It isn’t as extravagant as the ladies’, but I always wear some sort of straw fedora with a wider brim. I add a little flair with a hat pin and feather. A close second is a bow tie. Otherwise, it’s the overall look. My Derby outfit should be a little bolder than what I might wear to the office or to a wedding. It should be dressed up, but not formal.
This year’s shopping session definitely did not disappoint. Heath chose to go all-in on patterns with a light-blue check shirt layered under a royal-blue plaid sport coat. (Per usual, his straw fedora is donned with a hat pin and eye catching feathers.) Julie’s picks were just as striking, thanks to a bright red ruffled dress and polka-dot sun hat. And in case you didn’t notice, Heath’s bow tie matches Julie’s dress, while Julie’s earrings are a subtle nod to Heath’s blue-on-blue get up.
Let us help you create traditions of your own with our awesome personal stylists. If you’re in Boston, Chicago, Dallas, DC, Los Angeles, or New York, and are wondering what all goes into a Clubhouse appointment, you can read about it here.