DANIELLE REGO and
NICOLE SHOCKLEY
THE OWNERS OF JOSEPHINE
1405 North Wells Street, 312-274-0359; josephineonline.com.
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Rego and Shockley opened their shop only five
years ago, but they share a sense of style that seems to go back to the womb-perhaps because they are twins. They continue to evolve their offerings each season with shoes that are sexy, sleek, and, yes, ladylike.

IN THE BEGINNING DR: “When we were little girls, like two years old, we disappeared during a family party, and everyone was frantic until they found us in a closet. We had taken all the shoes out of their boxes.” NS: “No one lets us forget that!” MAGNIFICENT OBSESSION NS: “I remember obsessing about shoes in grade school.” DR: “I don’t think age matters; everyone is obsessed with shoes. Whether women are ten or 80, they are just as excited and love feeling pampered when they are trying them on.” SEASON’S BEST DR: “I cannot wait for the Giambattista Vallis to come in. They are spectacular.” NS: “Chic, with an edge. Giambattista designs for a lady, but he is using plaids, flannel, and suede, with a hidden platform in a stacked heel and a stiletto. I am also excited about Tania Spinelli’s collection. This is her fifth year designing, and every year she gets better. Her heel is very comfortable, and most of our customers come back for more.” LET IT SNOW NS: “I love snow boots. You don’t have to be in a funky clodhopper of a boot-we have two styles by Frye with a thick heel and a rounded or square toe, in dark purple or slightly distressed chocolate brown.” DR: “We also have a Jil Sander in charcoal or black, lined in shearling with a lug sole, and you can wear it pulled up high or roll it down. It’s very cool-looking, like a motorcycle boot.” MIX OR MATCH? DR: “I have always loved matching shoes and handbags. That doesn’t mean I always match, but I’m a sucker for the look.” NS: “It boils down to personal preference. It’s not as if there are a lot of rules in fashion these days.” OTHER THAN BLACK NS: “I wear all black, so my shoes are the spot of color, usually gold or red, but I also love a good black shoe. I have a zillion in my closet but never feel I have the right one.” DR: “There is a lot of patent leather for fall in all colors-plum, charcoal, black, and deep red. Patent is year-round, day to evening. For black tie, patent is absolutely fine.” GET WHAT YOU PAY FOR NS: “If you set out to buy designer shoes, you need to be prepared to spend $450 and up, and winter boots will be more. At the higher end, everything is made in Italy, and when you see the craftsmanship, you start to understand.” DR: “We are very conscientious about our price points. We can sell out of a full-price Rene Caovilla boot that is over $1,000, but the same customer will also demand something more practical.” WHAT’S THE BEST A SHOE CAN DO FOR YOU? DR: “They can make you feel thinner, taller, sexier, and better about everything.”

SCOTT STARBUCK
THE OWNER OF CITY SOLES & NICHE
1566 North Damen Avenue, 773-489-2001; citysoles.com.
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Starbuck, who opened his adjoining stores in 1996, continually swims against the tide in his choices of styling for men and women and even of locations. But in the end, he is rewarded for his prescience with a devoted line of followers, including a celebrity or two.

IN THE BEGINNING “I was 18, and all of my middle-class buddies were at Kansas University [Starbuck is from Kansas City], with new cars, apartments, and wardrobe allowances, and I was moving around, working, buying for a shoe store, and learning quickly how to succeed or fail. By the time those guys graduated, I had my own business.” RULE BREAKER “I go with my gut and buy the opposite of mainstream, and sometimes I get burned. But I learn. For example, normally I would turn away from ballet shoes, but they’re a great product for us. We buy the original Repetto French ballet flats; they are expensive, but the Chinese versions can’t compare in comfort, fit, or construc-tion.” WOMEN ARE FROM MARS “Women feel defeated if they have to shop too fast-they want to see the whole gamut of a style, and guys will come in and say, ‘Do you have it in brown?’ and be done with it.” HIGH STYLE “Every shade of brown sells for us-tan, cream, beige, espresso, chocolate-but for high-fashion colors, nothing stands out like a rich, dark green. Color for shoes is still important, like a burgundy or a wine, and color gives the consumer a reason to buy. Come on, everyone has five pairs of black shoes.” RISKY BUSINESS “Guys have gone from ath-leisure Pumas to dressed-up versions to wear with slacks or a sport coat. Right now the trend is British-brogue styles and wing-tippy looks to wear with jeans. People aren’t trying to look crazier than they are; it’s hip now not to be junked up with piercings, tattoos, and trashed $400 jeans.” FIRST UP “We have helped pioneer lines, and sometimes they outgrow us. For example, we were the first to import Chie Mihara from Spain, and now it has started to sell to department stores. It had phenomenal military-influenced boots that were very understated, with worn brass buttons up the side and a small granny heel. They were $500, but for us were a winner. Ten years ago, I also knew that a busy corner like [Damen, North, and Milwaukee] would be a great location for walk-in traffic.” COOL OR UNCOOL? “No matter how cool we think we are, we still sell four pairs of everyday black or brown shoes for every pair of yellow patent leather ones.” FAMOUS FOLLOWERS “We don’t have a super A list but a handwritten note on the wall of famous people who have shopped here-Liz Phair, Jeremy Piven, Dennis Franz, the Real World cast from Chicago. But sometimes, one of the kids will say, ‘Dude, that’s the drummer from God-smack’ or something, and I won’t have a clue.” WHAT’S THE BEST A SHOE CAN DO FOR YOU? “Get you laid.”

TAMARA MELLON
THE FOUNDER AND PRESIDENT OF JIMMY CHOO
63 East Oak Street, 312-255-1170; jimmychoo.com.
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Mellon garners international headlines for her glamorous globetrotting as much as for her
elegant style. She set off a frenzy when she stopped in to say hi to her fans at the opening celebration of her Oak Street store earlier this year.

IN THE BEGINNING “My first shoe memory was in Paris-I was five and on a trip with the nuns of my convent school when I saw a tiny pair of cowboy boots in a store window. They were so cute, and I made such a fuss that the nuns had to buy them for me. They were expensive, and I know they dreaded telling my mother about them.” U.S. INTRODUCTION “It usually takes European brands 20 years to translate properly to the American market. But within a year of opening the company [in London ten years ago], we had a store in Los Angeles, and the global publicity of young Hollywood made us an immediate hit.” THE BIG DIFFERENCE “The quality is amazing. We work on the details of the last [the shape] and the balance. That makes our shoes comfortable, and a woman is able to wear a higher heel than usual. Shoe trends always change, but a Jimmy Choo should never date, and many of the designs can take you from jeans to a black-tie event.” GETTING USED TO HEELS “I always tell women, If you’re not used to walking in high heels, buy a pair and practice by doing the Hoovering in them.” FALL’S MUST-HAVE “An ankle boot crosses all fashion trends and looks wonderful with a skirt. Ours hit just below the ankle, in a flattering place on the leg; you have to be careful so the vamp doesn’t cut you off. Wear them with dark hose-black or brown-not a flesh color. We also have a pump called Sweden that’s a modern take on a plain pump. I’d go for that in black.” CALLING THE TRENDS “We worked on a lot of wet looks, patterned leather done soft and slightly wrinkled. There are interesting finishes, and buckles are back in gold. We have an ankle boot with three gold buckles up the side, with a heavier, thicker heel-it is very chic.” WHAT’S THE BEST A SHOE CAN DO FOR YOU? “It completely modernizes your outfit. If you don’t want to buy new clothing, modernize with new accessories.”

LORI ANDRE
THE OWNER OF LORI’S DESIGNER SHOES
824 West Armitage Avenue, 773-281-5655, and other locations;
lorisshoes.com.
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Nothing will keep women away from Lori’s Designer Shoes; in fact, a blast of bad weather-or good-is always great for a new season, and for the business of one of Chicago’s true retail phenomena. Andre now has six shops in the city and the suburbs.

IN THE BEGINNING “When I opened 24 years ago, Armitage Avenue wasn’t a fashion mecca. Across the street from our first location was a shack where you could get your tires changed. I felt like we needed a guard dog then! It was seedy and unsafe, but we brought in pretty, unusual shoes that had not been seen in Chicago. The concept of the styles, the shoes out on the floor, and do-it-yourself service really appealed to people.” PUMPING IT UP “We have always sold a working-girl pump. The style changes ever so slightly each season, with a kitten heel or a thicker, straighter heel. Girls used to come in asking for navy shoes to go with their navy suits, and now we have trained them to wear black patent or brown with their navy.” ON THE TRENDS “It’s never good to be too early with the trends, but we’ll get the edgiest styles that we think will sell. This season, purple and gray are colors we think will do it.” WINTER WONDER “I love it when people try on $400 leather boots and ask if they can wear them in bad weather. I tell them to find winter boots that are waterproof-we carry Aquatalia and La Canadienne, which are fashionable and functional.” PERSONAL FAVORITE “Riding boots; stylistically they have such sophisticated elegance. Typically they are flat, with a rounded toe and a clean shaft [the leg]. Pair them with a great jacket, a white blouse, tuck in your pant legs, and throw them on with everything.” MORE FAVORITES “I love high-heel, pointy-toe slingback pumps. This season I am buying a nutmeg-colored patent Mary Jane version, that and a basic black.” ON THE LOW DOWN “People are still digging flats; some people still want a loafer or a driving moccasin, but this season is strong on dresses, and as long as there are dresses, people will want ballet flats.” WHAT’S THE BEST A SHOE CAN DO FOR YOU? “Make you feel great and worry less about your weight.”

SHERRIE OPPENHEIM, LORI MILLER, and BRANDI SECHER
OPPENHEIM IS THE OWNER OF SHIRISE,
AND SHE AND HER DAUGHTERS, MILLER
AND SECHER, ARE THE BUYERS.
341 Park Avenue, Glencoe, 847-835-2595; shirise.com.
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Oppenheim brought her daughters up surrounded by the shoes that she lovingly chose for her groundbreaking North Shore store, which she opened in 1985. Now they help her buy not only shoes but bags, jewelry, and other fashion essentials.

IN THE BEGINNING SO: “The name ‘Shirise’ sounded fancier than ‘Sherrie’s Shoes.’ My parents had a clothing store, but I really learned about shoes at Neiman Marcus.” BS: “Where she was the number-one salesperson in the whole Neiman Marcus system.” SO: “Well, I could remember everything in my customer’s closets.” LM: “She would stay at work late and go out of her way, calling because she had found what they were looking for.” SUFFERING FOR STYLE? BS: “Absolutely not! But I will go up a size if it is a great shoe, like a handmade, embroidered Emma Hope that I really love.” SO: “Taryn Rose is a foot doctor turned shoe designer who cares about fashion but was tired of her feet hurting, and we have been with her since she started. I wear a lot of her shoes and three years ago had to have surgery on a femur fracture, and they were still comfortable.” WALK ON SO: “If you are trying to spare your feet, don’t wear a pointy toe. Wear lower heels, or a thicker heel for support. Don’t buy the 100-millimeter-it’s four inches. Go a little lower, even if it’s just to 90 millimeters. There is a big difference. Fall’s shoes put the platform on the inside of the shoe, so the pitch is less, but it still looks as if you are walking on a three-inch heel. Actually, it’s just two and a half because of the platform.” LM: “Our customers can take a shoe home on approval and walk around on their carpet and get a feel for it.” THE NEW BLACK SO: “Gray-or any shade of metallic gray. It looks good with denim, and the pewter tones are neutral.” BS: “Black patent and snakeskin in shoes and handbags, or pony. We push people to buy other than black; we get tired of it, and it’s too much the norm.” FAVORITE LABELS BS: “Robert Clergerie, Elisa Ferare’s shoes with stones-not too zaza but sophisticated-and I love Pedro García, and Chloé and Emma Hope for a really pretty shoe.” SO: “I wear Jimmy Choo for evening, and I do like Elisa Ferare; she is very fashion-forward, and she mixes suede with metallic trim. Her shoes are unique, and even look kind of handmade.” SHINE ON BS: “Metallics are never going to go out of style, since they work with too much. With a long black dress, I’ll bring in a bronze shoe and a turquoise wrap. Accessories don’t all have to go together.” LM: “Metallics update your wardrobe. Your figure changes, and maybe the season’s skinny black pants or jeans are not for you, so update with a beautiful metallic.” CLOTHES CALLS LM: “We like it when customers bring in their outfits so we can help them with the right shoes.” BS: “Our customers seem to need to match, but I don’t believe in it. We help them pick something different that works.” LM: “So choose metallic gray or winter white to go with your black suit.” WHAT’S THE BEST A SHOE CAN DO FOR YOU? SO: “Make the whole outfit. The right outfit and the wrong shoes don’t work, as far as I’m concerned.”

Photography by Jeff Sciortino