THE CHOSEN ONE
Kacie Starr Triplett
St. Louis Alderwoman
Adam Says: "A wool camel coat is a foolproof investment: Buy once; wear over everything. Forever."
"This double-knit dress is worth every penny—the stretch fabric and color blocking instantly make you look a size smaller."
Kacie Says: Whether advocating for the homeless or helping to bring in $80 million to revitalize the city's downtown area, Triplett embraces a grown-up wardrobe of classic sheath dresses in vibrant colors. "As a public official, I don't make a lot of money, but I do believe in buying quality fabrics," she says. Triplett, who recently turned 30, wants to be taken seriously but still likes to dress her age. This affordable double-knit dress transitions from meetings to evenings out with friends; a camel overcoat is sleek and professional.
Deal Maker's Instinct
"I don't pretend to know all the answers, but I have some natural reflexes. I can be aggressive when the need arises. My community didn't elect me to be a wallflower."
Dress, Alfani; $89. Overcoat, Talbots; $399. Earrings, Melinda Maria. Ring, Kara by Kara Ross. Shoes, Manolo Blahnik.
Next: Pants that resist wrinkles and a dressed-up peacoat
Jennifer Rudolph Walsh
Worldwide Head, Literary Department, William Morris Endeavor
Adam Says: "A sequined peacoat is such a modern way of dressing: Day meets evening, plain meets fancy."
"These pants are made from synthetic silk, which is less prone to wrinkle. They won't live at the dry cleaner's."
Jennifer Says: For Walsh—who spends her days making deals for big-name writers and her free time hanging with her three children—shopping means plowing through department stores in a "practical, almost forensic" manner, grabbing up easy-wearing basics that go with everything. A splurge like this silk crepe cowl-neck shirt will look as good with her favorite jeans as with a pair of fall's trendier pleated trousers, especially when layered with an embellished peacoat and finished with strappy sandals. Walsh understands the value of a little glitz: For her 40th birthday she bought herself "a gorgeous pair of diamond earrings that I earned and will pass on to my daughter."
Deal that Got Away
"The Time Traveler's Wife is one of my all-time favorites. A few years ago, I met the author and said, 'Oh my God, I love your book so much.' She said, 'Really? Because I sent you a query letter and you rejected it.' That was devastating, but obviously she did just fine without me."
Cowl-neck shirt, Donna Karan New York; $895. Pleated trousers, Club Monaco; $129. Embellished peacoat, Tommy Hilfiger; $698. Sandals, Dolce & Gabbana. Rings, Martin Katz, Wendy Mink Jewelry.
Next: A dress that can take you from the boardroom to an edgy rock club scene
Cochairman and COO, Atlantic Records
Adam Says: "These days every brand is doing statement jewelry. No matter how much (or how little) you spend, it looks great piled on."
"There's no need to shell out for a high-fashion shoe you'll wear to death for just one season. These are only $55."
Julie Says: "Monday to Thursday, my outfits need to transition." This sexy gray dress is the kind of piece that can take her from the boardroom to the "dirty little rock clubs" where she checks out bands. "For day I'd wear it with a jacket or funky jewelry, and some really sick shoes," she says. "Later I'd add more eyeliner and I'd be ready to go!"
"Signing Death Cab for Cutie. They were a cool indie band, and for them to sign with a major label showed fans and critics we're interested in helping artists sell more music. It was important not to mess it up."
Dress, Obakki; $334. Earrings, Rachel Rachel Roy. Bracelets, Simply Vera Vera Wang, Ann Taylor, and Loft. Ring, V by Eva. Shoes, Aldo.
Next: Your new go-to jacket, plus a dress you can wear to work and then out at night
Alexandra Wilkis Wilson & Alexis Maybank
Founders, Gilt Groupe
Adam Says: "The luminous woven cotton and unusual color make this jacket extremely versatile."
"If time is money, searching online for precisely what you want can save you both."
"Nude pumps are a must. They elongate the legs, make you look thinner, and can be found at every price."
Alexandra and Alexis Say: "In the fashion community, it's important to look the part," says Wilson (far left). When she and Maybank greet customers at events, they "dress to the nines!" Of course, that requires a little planning: Says Maybank, "I'm partial to dresses I can wear to work and then out at night," like this one by Richard Chai. "And I always have high heels, plus a pair of flats for running around." Wilson dresses up black pants with sexy sandals and a Hugo Boss jacket that she'll shed come evening.
Art of the Deal
"In negotiating, you need tenacity and a big smile," says Maybank. "I don't take no for an answer," adds Wilson.
On Wilson: Pants, Michael Michael Kors, $70. Sandals, Chanel. Jacket, Hugo Boss,(originally $795, now $319 on Gilt.com) JBracelet, Cara Croninger.
On Maybank: Dress, Richard Chai, (originally $1,175, now $299 on Gilt.com). Bangles and cuff, Robert Lee Morris. Shoes, Casadei.
Next: The power color that works as a neutral for day or night
President of History and Lifetime Networks
Adam Says: "When springing for pricier separates, make sure they go with at least four other items in your closet."
"Solids can be worn more often than distinctive prints. Put your money on timeless clothes that fit your figure brilliantly."
Nancy Says: "I didn't know I had a style—I'm usually just trying to get out of the house without Cheerios on me," says Dubuc, a mother of two. But she's learned to be more "strategic and thoughtful" about her purchases, choosing well-made pieces in solid colors that will take her to meetings on both coasts. This dove gray linen suit jacket and ruched jersey pencil skirt will feel modern for years, especially matched with simple pumps, like this patent leather pair by Yves Saint Laurent. "I'm 511, so I wasn't always a fan of heels," she says. "But a lot of people in my life are telling me to put them on."
Landing the Deal
"My job is to rally the troops to craft a vision, then let them do their thing. It feels great to get a project before your competition."
Suit jacket and pencil skirt, both Donna Karan New York, skirt, $795. Watch, Tag Heuer. Ring, Rarities by Carol Brodie.
Next: The power color that works as a neutral for day and night
Vice President of New Site Development, Teach for America
Adam Says: "Depending on accessories, this dress can go formal or casual."
"If you're playing with color, try red. It's now accepted as a neutral, even for day."
Ifeyinwa Says: "I have a favorite pair of red shoes I call my power heels," says Offor, whose negotiation skills have helped Teach for America raise nearly $40 million and expand to eight new cities in the past two years. "If I'm wearing something bright, I feel ready—so bring it!" Here, she goes for the bold, pairing a cap-sleeved dress with peplum ruffle and two chunky necklaces —a look equally appropriate for school visits and dinners with donors. "Black is a uniform," says Offor. "You have to spice things up every once in a while."
Let's Make a Deal
"Nothing gets done without building relationships. I'm willing to listen. If you want to rant and rave or feel like you just need to be heard, I can do that."
Cap-sleeved dress, Calvin Klein; $128. Necklaces, Ann Taylor. Cuff, Noir Jewelry. Heels, AMI Clubwear.
Next: A wild print gives some edge to a classic tweed jacket
Adam Says: "Tweed is a wise buy. It comes back every fall and works well with a variety of fabrics and colors."
"A little leopard goes a long way. First time wearing a wild print? Don't spend a lot; see how comfortable you feel wearing it."
Amy Says: "My clients need to know I'm reliable and intuitive, but also social and outgoing," explains Laurent. "I would never wear a full-on pantsuit. That's not me." A pencil skirt with an edge—like this very affordable leopard-print one—looks "cerebral but sexy" with a tweed jacket and a pair of oxford heels. "You can dress in a way that sends the message you're a professional and that celebrates being a woman at the same time," Laurent says.
"If someone thinks he's going to place an order for a blonde between 5'6" and 5'7", I think, This person needs a therapist, not a matchmaker."
Pencil skirt, Alfani; $59. Tweed jacket, Diane von Furstenberg; $385. Oxford heels, Escada. Tank, Coldwater Creek, $35. Belt, Loft. Ring, Wendy Mink Jewelry. Cuff, Noir Jewelry.
Next: A universally flattering skirt that combines style and comfort
Vice President, Halstead Property
Adam Says: "Great investment—jewel tones go well with neutrals, and the wrap style never goes out of fashion."
"A circle skirt is flattering no matter your size, and once the longer-length trend has passed, it's easy to shorten."
Nora Says: "Heels make me feel put-together," says Ariffin, who always wears them despite spending her days "on subways, in taxis, or in town cars," scoping out as many as 12 apartments at a time for her exacting clients. These over-the-knee suede boots (MaxMara) provide comfort and lift, and they'll last forever ("I'm not one who follows trends"). Says Ariffin of her prewrinkled wrap blouse (Donna Karan New York) atop a newly stylish long skirt (Jones New York Collection, $99): "If I went into a meeting or a showing like this, I would exude confidence."
Sealing the Deal
"I gather the facts and let my clients be the decisionmakers, because I don't want to force someone to make a purchase they don't love. My reputation is at stake."
Suede boots, MaxMara. Wrap blouse, Donna Karan New York. Necklace, Jack Vartanian. Belt, Bottega Veneta.
The workwear separates you need to keep you looking polished and professional