Meet Your Neighbor: Wendy Osborn, Chloe’s of Middleburg Boutique Owner, Shares a Fresh Perspective on Life and Fashion

By Summer Stanley | Photos by Jennifer Gray

“No winter lasts forever. No spring skips its turn,” wrote American author Hal Borland nearly 60 years ago, reflecting on his love of nature and the outdoors. Those words still hold true, after weeks of our walls seemingly closing in at times, and April now in bloom. It becomes easier to notice an abundance of cheerful details around us, perhaps overlooked before.

The blue butterflies permanently adorning the storefront sign at Chloe’s of Middleburg appear as if at any moment they might flutter away to land on a nearby flower. Store owner Wendy Osborn, who opened Chloe’s in July of last year, sees the butterflies as a sign of life, transformation, and hope, and for a women’s apparel boutique, there’s no better welcome than that.

Osborn’s path to Middleburg actually began in the Northeast. Raised in Princeton, New Jersey, memories of her childhood include traveling and going into Manhattan with her parents for the theater. “I’m grateful that they were able to provide so many experiences for me then,” remembers Osborn. “My family definitely shaped who I am today.” Remarking that her mother had fabulous taste and shared her love of butterflies, Osborn also takes pride in her grandfather’s history of running a successful restaurant in Princeton starting in the 1930s. “The entrepreneurial spirit is in my blood,” Osborn says. “I guess I had always wanted a little shop or business of my own someday.”

Osborn received her fine arts degree from Rhode Island School of Design, majoring in textiles and printmaking. After college, she wanted to be a part of bringing good design to the consumer and began working at the notable Betty Parsons Gallery in New York City. Parsons was a pioneer in advocating for the abstract expressionist and avant-garde art movement in America, running the gallery until her passing in the early ’80s. It was shortly after that when Osborn moved on to a career with Bergdorf Goodman, which was just across the street on 57th. Surrounded by designer labels, she spent only three months in sales before moving to a buyer role in women’s fashions. When she was approached by then Chairman and CEO Ira Neimark to ask if she’d be interested in buying for the gifts and stationery department on the seventh floor, Osborn quickly responded, “I can get excited about a pencil!”

Eventually finding herself in the Washington, D.C., area with Neiman Marcus management, she soon fell in love with the gentle kindness of Hunt Country after many jaunts to the countryside for the polo circuit and antiquing. “Love brought me to Virginia and it has kept me in Virginia,” Osborn says. Her family’s move to Upperville six years ago was also driven by the strong education opportunities available to her children. When her daughter, Chloe, prepared for a move to college, she was ready for her next creative venture. “I knew the timing was right when I saw the lovely vacant storefront on Washington Street waiting for me,” Osborn shares.

It’s not just her appreciation for consumerism and collecting things, but it’s how she notices the beautiful details in everyday life that really feeds her soul. “I sometimes look up and just marvel at the clouds, even pointing them out to my grown kids,” Osborn says. She decided to make daydreamed clouds another visible icon of her new store by using the artistic talents of her daughter, who beautifully hand-painted the clouds found in one of the storefront windows.

Osborn’s passions here are many — philanthropy, gardening, and when it comes to painting her own artistic vision, Osborn explains the store is her palette now. So just as a gardener would see fit, Chloe’s is a store for women of all seasons. “We see three generations shopping together — the daughter, mother and grandmother,” Osborn says. Make no mistake about it, the shop carries fashion forward items alongside the classics, but she makes sure only the best and most tasteful items of a trend are made available at affordable prices. “People are living and working longer with active lifestyles, so we’ve adapted when it comes to fashion. We’re all dressing younger in spirit,” Osborn says. “Our looks at Chloe’s are fresh and alive, a good value, and always appropriate.”

When looking for what to bring into the shop, Osborn joins the ranks of other businesses who attend the seasonal buyer markets, most recently in NYC and Atlanta earlier this year. “We’re all scouring the market to see what’s out there,” Osborn explains. There are hundreds of vendors and thousands of items to look through, as Osborn curates collections to bring home to Chloe’s and Middleburg. “I’m like a kid in a candy store when those deliveries arrive at the shop ready to open!” Osborn says. She receives new shipments a couple times a month, so it’s always worth a visit to see what’s changed on the floor.

At Chloe’s, you’ll find styles covering the decades, but the one trend that’s always coming back, whether in fall or spring, is animal print. The variations keep it fresh, such as the unexpected colors added to it this season, or how we’re seeing more snake print than before. Tie-dyes, ombre effects, and neons are also having their moment again, in addition to plenty of whites, pinks, and florals for all the spring feels. You’ll find some polka dots popping up at Chloe’s, along with new ways to incorporate leather into your look. Interesting sleeve details continue to be happening, like puffed or ballooned sleeves in blouses and dresses, as well as asymmetrical ruffles or tiers on the bottom of a maxi dress.

If you tend to shy away from bold trends but still want to have fun, Osborn offers this tip: “For the faint of heart who can’t do the neon dress, maybe choose an accessory like a scarf or bangle bracelet in neon or animal print.” While Chloe’s offers jewelry and bags for the accessory lovers, the real performing show-stopper has been their comfortable and breathable flats by Ilse Jacobsen. Women who end up living in them, come back to buy every color of the Danish-designed shoes. Chloe’s also offers some no-iron fabrics, which are great for business or travel, as well as an assortment of both imports and “Made in America” labels.

When you’re shopping for others, you’ll find plenty of gift options like soaps, hand lotions, or sachets that are easy and affordable tokens to pick up on the go. Of course, Chloe’s keeps their equestrian friends and spectators covered, too. A Middleburg themed private-label blanket, designed by Osborn herself, is perfect as a keepsake or for tailgating, and large enough for snuggling.

Osborn is always on the hunt for quality and fun items that bring a great balance to the boutique. She wants women to leave the store feeling empowered and confident, and that’s just what’s happening at Chloe’s. What sets them apart is their excellent customer service. It excites Osborn to be able to style her clients, but she and her team are easygoing. “Some customers know their styles and exactly what they want when they come in, but we are always ready to give personal attention, whether to visitors just passing through, or to the locals,” Osborn says. “The team knows my customers as well as I do, and we all work together to create a great shopping experience.”

It’s truly Osborn’s positivity that spreads this social butterfly’s kindness out into the world. “I always ride the wave, stay upbeat, and look for the positives,” Osborn says. “I don’t let things bother me. We keep Chloe’s a happy place to be, and for our customers, too.”

Come in and say hello next time you’re walking around Middleburg, or if you see the Chloe’s pop-up tent at a local event. Follow @chloesofmiddleburg on social media and visit chloesofmiddleburg.com for more information. ML

This article first appeared in the April 2020 issue of Middleburg Life.