Dressing Up with Jenny Walton: The Vintage Fashion, Jewels and Unexpected Antiques She Adores

By Stephanie Sporn

W atching Jenny Walton thumb through her candy-colored garments by Dries Van Noten and Miu Miu in her charming Nolita apartment, I have a hard time imagining her donning the baggy basketball shorts she insisted was her standard childhood getup. “I was very much a tomboy who was into whatever was the comfiest,” Walton tells Sotheby’s. My, how times have changed. Now a globetrotting fashion illustrator and rising style icon admired for her feminine mix of retro silhouettes and whimsical accessories, Walton invited us into her home, shared with fiancé Scott Schuman and two picture-perfect dogs, to play dress up with her fabulous wardrobe and pieces from Sotheby’s Jewels Online auction. As the mastermind behind street style blog The Sartorialist, Schuman lent his expertise by photographing Walton for this shoot. Ahead, discover more about the evolution of Walton’s personal style and see the jewels from our sale that most caught her eye.

“I tipsy-bought this Dries Van Noten sweater and skirt last season in Paris after having a glass of wine with lunch. I love these colors and think they pair perfectly with gold jewelry. This double-face bracelet-watch may be my favorite piece in the auction.”

What are some of your earliest memories of collecting and discovering your love of antiques?
My mom is the most thrifty woman. She would take my sisters and me to flea markets and estate sales and give us $5 to spend however we wanted. When I was around ten I actually collected old man smoking pipes. I loved their shape and thought they were beautiful, and they were often really cheap because they were filled with tobacco and basically cracking. Because people thought it was funny that a little girl wanted a smoking pipe I could get them for 50 cents or a quarter, so my $5 would go very far. I also started collecting 1950s kitchenware when I was little. I began appreciating older items that were more unique than what the kids around me growing up would typically get at the mall or places like that.

Were you always as interested in jewelry as fashion?
My sisters and I watched old movies with our mom, and I think my idea and love of fashion came from women like Joan Crawford, Bette Davis and Barbara Stanwyck in glamorous gowns. Looking back I feel that jewels were definitely a part of that. Because a lot of the movies were in black and white, the jewels needed to sparkle like crazy and be high contrast. Jewelry added this whole element to the stars’ personas.

“This is my evening jewelry look where we mixed silver and gold with my Jacquemus dress.”

What is the story behind your vintage engagement ring?
Scott and I go to Milan a lot for Fashion Week, and it’s our favorite of the different cities. There’s a beautiful little jewelry store there called Gioielleria Pennisi, and when we started talking about getting engaged I told him that we could only buy the ring from there. We got engaged at the Armani Hotel next to it, so I loved the idea of the different elements of our marriage and courtship being based in a city that we love so much. Each time we were in Milan for Fashion week we would visit Pennisi, and it took at least a year to find this ring. It’s a toi et moi ring from about 1900, and it’s probably Austrian.

There’s nothing like these small antique jewelry stores in America, especially not in my small hometown in New Jersey. These amazing tiny storefronts that have a curtain in the window and a little buzzer. I’m equally intrigued by the displays of jewels in their original boxes. The crushed, faded velvet in beautiful blues and greens and reds. Now packaging is often just thrown away, but these pieces have been preserved and cherished for so many years.

"I really love jewelry that has a floral motif, so I was immediately drawn to these Seaman Schepps earrings and Chanel bracelet-watch. The earrings have a vintage feel that complements this Victor Costa dress that my mom bought for me at an antique store."

What are some other jewels you wear regularly?
I generally like jewels from the Edwardian, Georgian and Victorian eras, and I also like pieces from the 1950s for something more modern and fun. I have a pair of screw-back crystal stud earrings that I wear almost every day. They bring out the brightness in my eyes. Lately I also wear a 1950s enamel daisy bracelet. Even though the paint is chipping away, it's a piece that makes me really happy.

Inspired by your hair pin tutorial, do you have any jewelry styling tips handy?
I have one or two really long necklaces that I wear as belts. I collect and wear a lot of 1950s mid-century enamel flower pins, and I recently wore one to help close the bottom of a top. You can wear them in so many ways. Another thing I do is stack vintage wristwatches. None really work, but I think that’s kind of funny.

“I love and collect vintage compacts. They are such a chic accessory to have in your purse, especially if your phone dies, and you need to see if your lipstick looks okay.”

Do you have any favorite vintage or contemporary jewelry designers?
I am friends with Roxanne Assoulin, and she does such a great job making modern jewelry that’s still very fun. Her hashtag and concept is “uncomplicated indulgence.” Miu Miu also does fun costume jewelry. Most of my vintage is unsigned, but I do have some Lea Stein foxes.

Given your background in fashion design and illustration, do you think you would ever create your own line?
Yes! I am enjoying rediscovering design with jewelry and hair accessories, and hopefully in the next couple months you will see some of my own pieces launch.

Stay informed with Sotheby’s top stories, videos, events & news.

Receive the best from Sotheby’s delivered to your inbox.

By subscribing you are agreeing to Sotheby’s Privacy Policy. You can unsubscribe from Sotheby’s emails at any time by clicking the “Manage your Subscriptions” link in any of your emails.

More from Sotheby's