This body-skimming, rose-patterned shift (Kate Spade, $345) is balanced by a swingy coat that you don't have to diet to get into (Elie Tahari, $798). "Grace Kelly was iconic, and I think my character wants to emulate that," says January Jones, who plays Betty, the wistful wife of philandering advertising executive Don Draper on Mad Men. "Grace and Betty both have the same stoic melancholy."
Necklace, Subversive Jewelry by Justin Guinta. Clutch, Michael Kors.
It's in the Details
A comfortingly slouchy "boyfriend" sweater (Gap, $68) thrown over the shoulders is a chic way to relax between takes. The straight silk skirt (Paul Smith, $965) features a hint of black lace at the hem—a tongue-in-cheek detail that makes it look as if her slip is showing. A bolder, less-repressed take on the '60s is on view in January's new movie, The Boat That Rocked. A comedy, out next year, it's about a pirate radio station off the English coast. (It co-stars Philip Seymour Hoffman and Kenneth Branagh.)
Turtleneck, Gap, $42. Brooch, Carolee Lux. Watch, David Yurman. Rings, Diamonair.
Look Smaller in Skirts!
Big, crisp skirts make your waist look tiny, flatter broad hips, and produce a satisfying swish. Try one in floral taffeta (Jason Wu, $1,300), but keep it casual with a fitted turtleneck in a coordinating stripe (Vince, $85). Mad Men costume designer Janie Bryant is a stickler for historical accuracy, so January's character is polished on the outside—"She dresses up to go to the market!"—and authentic right down to her undergarments (her bras have tips for a pointy effect).
Complement this casually sophisticated look with fresh, flawless skin and bold, matte lips. To get a creamy complexion, brush on either a matte-finish liquid foundation (try Shu Uemura Face Architect Smoothing Fluid Foundation) or a mineral powder (like CoverGirl TruBlend Pressed Mineral Foundation), says Christy Coleman, the makeup artist for this story. For a Grace Kelly mouth: Outline your lips with a liner that matches your natural lip color, and then blend to soften the edge. Finish with a matte, coral-tinted lipstick (like YSL Pure Lipstick in Rosy Coral).
What Would Grace Do? Dress Your Waist
An impressive 34-24-35 during her years as a star, Grace highlighted her measurements with clothes that accentuated her waist. You can channel Lisa Fremont, her high-society working girl character in Rear Window, and wear a belt to cinch your midriff.
You Can Do Trends!
This marvelous dress mixes two fabrics: a silk crepe satin bodice with distinctive cutouts and a wool blend skirt (3.1 Phillip Lim, $595). The faux-fur jacket (Juicy Couture, $478) should be worn nonchalantly, tossed over the shoulders and paired with everything from jeans to a gown. The glamorous aura of these clothes reminds January of Grace's "phenomenal" wardrobe in To Catch a Thief: "It was a time in film when everyone looked like $3 million."
Bag, Jimmy Choo. Ring, Dana Rebecca Designs. Watch, Seiko. Shoes, Michael Kors.
Sheer femininity prevails as January powders her nose in a ruffled blouse (Milly, $340) and pencil skirt (Calvin Klein, $98). The design of Grace's celebrated Hermès bag dates back to 1935, but in the '50s it was redubbed the Kelly because she carried it constantly, even using it to conceal her pregnancy from the press.
What Would Grace Do? Don't Forget the Accessories
Grace was the queen of accessories (remember the elegant Mark Cross overnight case she pulls her sheer chiffon peignoir out of in Rear Window?). This fall, gloves, a charm bracelet, and sunglasses (to give mystery) add Hollywood glam.
Mixing Then and Now
French twists are looking stylish again, especially with a sweater and pearls—all Kelly trademarks. Although the camel pullover is classic (Lauren by Ralph Lauren, $100), the necklace explodes into a dazzling bib of pearls and Swarovski crystals (Tom Binns).
A retro-active wool blend sweater jacket (Dressbarn, $40) has everything going for it, including a double-breasted shape that lets it stand in for a blazer. Try it with a pencil skirt for work or with cropped pants and flats on weekends—the sort of elegantly casual outfit Grace relaxed in.
Ring, Jennifer Miller.
The Shirtdress: Reinvented
The reinvented shirtdress in brown silk wool (Tadashi Shoji, $950) has short sleeves that knot and tie instead of roll up. It can be worn either cinched with an embossed leather belt (Michael Kors) or left open for when you want a looser feel. Necklace, Janis by Janis Savitt.
Bracelet watch, Van Cleef & Arpels.
Unmatched pieces can look as finished as a suit—like this silk wool floral shell and skirt (Michael Kors, $995 and $950) and swing coat (Rebecca Taylor, $520). The Kelly-esque bag (Tod's) is less structured than the original. January loves vintage but avoids '60s styles because "people will think it's silly, like I'm very Method, staying in character in outfits from work!"
Bracelet, Diane von Furstenberg by H.Stern. Shoes, Michael Kors.
Pop with Spiced Up Jewelry
This gray flannel short-sleeved shift dress (Liz Claiborne, $199) has an accommodating shape that can handle a real body. A distressed-leather belt (Marni) evokes the waist-conscious '60s, while the eclectic necklace (Janis by Janis Savitt) links gold motorcycle chains with an antique-looking brooch—a playful take on the sedate jewelry that was a Kelly signature.
Shoes, Claudia Ciuti.
Simple Yet Stunning
The ladylike drape of this delicious cream wool sheath (Louis Vuitton) reminds us that serious tailoring ruled in Grace's day: Quality clothes were painstakingly sculpted, twisted, and tucked into a structure that fit exquisitely (and often improved the look of the body underneath). This dress has slimming vertical seams and a flattering open neckline that invites a striking Art Deco–style brooch (Louis Vuitton). January likes it with simple, pulled-back hair and minimal additions: "The amazing detail speaks for itself."
Bracelet, Janis by Janis Savitt.
What Would Grace Do? Make the Best of Any Situation
Grace was scheduled to meet Rainier III, Prince of Monaco for the first time in May 1955 at his palace in Monaco. That morning the electricity went out at her hotel, and she was unable to dry her hair. She toweled it off, pinned it up in a chignon, and chose a distracting floral dress.
The Golden Age
Gold brocade, like this covetable knee-length dress (J.Crew Collection, $328), is unforgettable. "It's my Evita moment!" says January, poised on a balcony. In the '60s, magazines photographed stars at home with perfect discretion: "You didn't know every single dirty thing about every celebrity," January observes. "There's something to be said for a bit of mystery and reserve."
What Would Grace Do? Keep a Sense of Humor
According to her friends, "Gracie" had a delightful sense of humor that offset her patrician beauty. On March 9, 1981, Lady Diana Spencer (who had just become engaged to Prince Charles) met Princess Grace at a charity event in London. She reportedly asked her advice about marrying a royal. "Don't worry, dear," Grace is said to have told her with a smile, "it will get worse."