A glimpse inside the voguish closets of one of Chicago’s most fashion-forward couples

Photography: top Anna Knott,
all others Gillian Koenig

Amand and Gregg Shipp of Chicago
Gregg and Amanda Shipp touch base in their Wicker Park living room.
Gregg Shipp's favorite shirts
Two of Gregg’s top choices

Amanda Shipp, the Chicago It girl and public-relations whiz, is sitting with her fitness-guru husband, Gregg, in their seventies-inspired loft in Wicker Park discussing one of their favorite activities-shopping. “Our first real excursion together was to Barneys in New York,” Amanda says with a laugh. “Gregg forced me to buy a pair of Dolce & Gabbana clogs, which I still have.”

Both now 36, they married last year, and a passion for design and each other has translated into shared success for this savvy couple. The effortlessly chic mix of new and vintage pieces spilling from their closets provokes wardrobe envy like few others. Gregg’s bold and singular approach to fashion-he frequently wears pants designed for women to flatter his slender frame and openly supports the male purse-helped win him a spot on CS magazine’s men of style list. He also garnered a sponsorship from the high-end apparel line Lululemon Athletica, and Time magazine recently acknowledged Gregg and his twin brother, Drew, for their success as the owners of the HiFi Personal Fitness Studio in Lincoln Park.

A New York native, Amanda is an alumna of Cornell’s renowned School of Hotel Management, the former sister-in-law of the celebrity chef Wolfgang Puck, and a past host of the Emmy Award–winning restaurant-review show Check, Please! This much-photographed woman about town, who describes her style as bohemian chic, is now the vice president of the Experiential Agency, a public-relations firm. She represents high-end clients such as the James Hotel and Jake, a boutique with locations on Rush Street and Southport Avenue. “I’m always around media and clients,” explains Amanda. “So I definitely have to keep up my appearance.”

Gregg Shipp holds up a tee-shirt
Gregg Shipp's boot
Amanda Shipp's gold shoe
leather pants
favorite shirts belonging to Amanda Shipp
Amanda Shipp holds up a favorite outfit
The mod pod: (from top) Gregg shows off his T-shirt collection; his Cloak boots and Amanda’s Yves Saint Laurent platforms; his custom-made leather pants; his Alice + Olivia slacks; her frocks by Matthew Williamson and Pucci; and her favorite outfit

To show me the highlights of their wardrobes, the Shipps take me upstairs to the master bedroom, where Gregg’s custom-made closets fill an entire wall. His collection of Dsquared2 T-shirts and brightly colored Alice + Olivia pants hang in one closet, while jeans, silk shirts, and vintage jackets-including a denim stunner by the rock star favorite Henry Duarte-line the other. The first thing Gregg pulls off a hanger is a pair of black leather lace-up pants. “They’re custom made, from a store in L.A. called Lord’s on Melrose,” he says, folding over the waistband to show me the silk lining. But what excites Gregg the most are a pair of tattered Ron Herman vintage jeans.   “They’ll never go out of style,” he says, pointing to an intricately stitched giraffe on the front and an elephant on the back.

The guest room serves as one of Amanda’s dressing areas and houses a collection of heels by Yves Saint Laurent and Gucci, as well as an armoire full of dazzling dresses. Among the standouts are a rose-and-cream Louis Vuitton dress that she wore to her wedding, a bright silk Matthew Williamson frock that she wears everywhere, and a long pink-and-black-print dress from Givenchy.

Amanda’s favorite outfit? “My Sass & Bide skinny jeans with my Doo Ri halter-top, an Yves Saint Laurent belt, and a shrunken jacket.” To finish it off, she throws on her high white boots or Yves Saint Laurent chunky gold heels.

The key to pulling off any look? Confidence, says this well-assembled couple. That is the true definition of style.

He Says:

“Invest in some good shoes. One pair of funky sneakers and at least one pair of dress and casual shoes that can take you from day to evening occasions.”

“The Dior skull necklace with diamond teeth that Amanda got me for my birthday. I love Dior-its jewelry is phenomenal.” • JB Classics white patent leather sneakers-“They come with their own certificate. Only 240 pairs were made, so I’ll wear these only in a controlled environment.” • Ron Herman vintage jeans-“I still freak over these. They’re the coolest ever!”

Cloak boots.

Ron Herman, Tsubi, Earnest Sewn, Ever.

Dsquared2- “Their T-shirts fit well.” • Lululemon Athletica-“For fitness clothes, because they’re spun with real silver, which has an antibacterial property.”

“Men need to get over the stigma of carrying a man bag. Cell phones, BlackBerries, keys, and wallets look horrible stuffed in guys’ pockets.” • “Rock your accessories. Hats, scarves, or key chains hung from belts pump up an average outfit.”

She Says:

“I love combos-just change a few elements, and you have a whole new look or outfit.”

“My mom’s vintage Fendi shopper.” • “Gregg’s mom’s collection of eighties boots that are perfect to wear over skinny jeans-they’re in pristine condition.”

Yves Saint Laurent, Pedro Garcia.

Sass & Bide, Nudie, Serfontaine.

Sass & Bide. • Matthew Wil-liamson. • “Any Missoni I can find at Filene’s Basement-they have a good stash!” • Doo Ri.

“Layer, layer, layer! A white tank with a sheer top, then a jacket.” • “Blend different designers-dressy and casual and vintage and new.”