“Jeans and a T-shirt can be as fashionable as an Oscar de la Renta dress,” says Simone Gensburg. “It’s all about wearing what you love.” In her elegant Hubbard Woods boutique, Simone shares her passion and knowledge of fashion with her clientele. As both a fashion consultant and friend to her customers, she perpetuates women’s irresistible love for clothes and accessories.
Photograph by Svetlana Eckhoff

When we first spoke to Simone Gensburg more than two years ago, she was a fledgling boutique owner. She has since established herself as a fashion expert along the North Shore, a title that is backed by the stunning and classic clothing in her elegant Winnetka shop. Carrying clothing lines by talented designers like Behnaz Sarafpour, Araks, and Nima, Simone is constantly on the search for the newest “It” designer, flying to studios in both New York and Paris. She conveys her fashionable knowledge not only through her store, but also via her personal relationships with her clientele.
Marla Wilneff of Glencoe has been shopping at Simone’s since the very beginning. “I was one of her first customers,” she boasts. She frequented the Hubbard Woods area for years, going to the nearby Kyoto Japanese Restaurant and running errands in the area, and was curious to see what would finally go into the storefront on Gage that had remained vacant for so long. Then one winter day, Simone’s appeared. “When I was walking by, I noticed her beautiful window, and when I peeked in, I thought it was really charming,” Marla remembers.
The two women bonded quickly over their love for fashion. While Marla enumerates all the fashion blogs and websites she frequents, Simone interjects, “Marla is really fashion-oriented.” But it wasn’t only their shared passion for clothing that attracted Marla to the store—it was also Simone’s personality. “Simone is very special because she’s very warm and very honest. She wants the customer to be happy and her store is a comfortable environment to shop in,” she explains.
When dressing up for a special occasion, Simone’s is usually a first stop for a beautiful dress. Sometimes clients will even tote over their own jewelry for Simone’s advice on how to wear it with the right ensemble. What many clients love best about the store is how timeless the pieces are.
Marla’s first purchase was a pair of black pants, which she still wears all the time. “Simone’s clothes are very classic and will take you anywhere…Even though [black pants] sound like such a basic thing to find, they fit perfectly and work with a lot of outfits,” she says. Likewise, she also bought a black cashmere poncho that she wears to death. “It’s a great piece—cozy, but it looks chic.”
She recently invested in a Ruffian black lace blouse from the shop, stepping a bit out of her usual comfort zone. But Simone showed her different ways to wear it that would make her at ease with the sheer fabric—under a blazer, with a black tank top, etc. “It was something I normally wouldn’t have bought here, but she gave me great fashion advice,” Marla says.
She also appreciates Simone’s willingness to adapt her store to her clients with ever-changing merchandise and designers. Originally, the store was filled with garments sized on the smaller side of the gamut, reflecting Simone’s own petite stature. As she got to know her customer base better, she expanded and got more sizes. She also changes the designers she carries in the boutique nearly every season—keeping things fresh and exciting.
But it is truly Simone’s classic taste in clothing that North Shore women like Marla appreciate and flock to. “It’s the simplicity of the clothes in here. They’re simple and elegant at the same time, and it’s an aesthetic that works for a lot of women,” she says.
Simone’s Boutique is located at 1060 Gage Street in Winnetka. For more information, visit simonesboutique.com, or call 847-446-9966.