BEFORE

Neil, a 28-year-old web developer, describes his style as “basic” and “easy” and likes to shop at Target and the Gap. His girlfriend, Brandi, a 28-year-old attorney, envisions a wardrobe that is professional but not dowdy. She doesn’t wear any makeup—and is looking for a new way to style her curly hair.

Photograph: Lisa Predko

WORK

NEW HAIR

NEIL’s stylist focuses on snipping the sides and cutting into the wave at the top. She sends him home with one product: Number 4 styling cream, which he is supposed to rub in for texture after he towels his hair dry.

BRANDI’s stylist conditions her hair with Moroccanoil products, then gives her a slight trim and straightens her hair with a round brush and hair dryer.

WORK CLOTHES

NEIL wants to get out of his rut of dark dress pants and collared shirts but doesn’t know how. The team decides he needs to inject color, texture, and a layer or two into his look. “I chose a purple shirt because it’s the new blue for men,” says Kate Shifrin, who added a blue sweater on top that “brings out the color of his eyes.”

Sweater, $188, shirt, $125, and trousers, $78, all from J.Crew. Oxfords, $295, from To Boot New York.

BRANDI has been hiding her size 2 figure under baggy mix-and-match separates that are comfortable and color blocked. The style team agrees that she could use a great print—in this case, a strapless dress—and builds a court-friendly outfit around it that silhouettes her figure. “The leopard-print belt gives it a twist,” says Shifrin. She picks a matching pair of leopard-print pumps.

Blazer, $178,shirt, $59.50, dress, $148, belt, $39.50, necklace, $98, all from J.Crew. Tote, $298, from Coach. Pumps, $265, from Charles David.

A MAKEUP TRICK

“Most women of color need to use more than one foundation to match their undertones,” says Laura Weathersby, who blends Becca Espresso and Becca Almond—two of her favorite foundation colors.

A NEW COLOR COMBO

Men often stick to dark colors; the style team suggests Neil should venture out and experiment with a more vibrant palette.

Photograph: Lisa Predko

WEEKEND

WEEKEND STYLE

NEIL tries on a pair of black and brown driving shoes from Billy Reid, and all agree that they will go with everything he owns. The same thinking applies to a gray jacket, which gives a basic striped shirt a trendy twist.

Jacket, $448, shirt, $88, both from Elie Tahari. Belt, $34.50, from J.Crew. Loafers, $325, from Billy Reid.

BRANDI is immediately drawn to a sparkly silver and white skirt from Club Monaco. “Wear what you love,” says Shifrin, who declares the skirt should be the building block of the ensemble. She combines it with a classic nautical-inspired top, which Brandi can wear with other items in her closet, and Charles David oxfords, since the couple often walks to restaurants and shows on nights out.

Shirt, $39.50, from J.Crew. Skirt, $179, necklace, $119, both from Club Monaco. Oxfords, $230, from Charles David.

A TOUCH OF CLASS

This flirty necklace looks old, but it’s actually Club Monaco. For a great vintage-inspired chain, rummage through your grandmother’s jewelry box for costume jewelry.

A TIP FOR MEN

Rolling up jeans is casual and fitting for mild weather—roll them down and pair with great boots for winter.

A SURPRISING SHOE

Not sure what shoes to pair with a flirty mini? Try oxfords—they’re unexpected and casual, and they ground the look.

A SEXY SHIMMER

The makeup artists give Brandi a smoky eye using black eyeliner by Prestige on her upper and lower lids. For sparkle, they apply a silver shadow from Makeup for Ever on her lids. They finish with Alcone lip palette No. 1 and Black Opal lip liner in Cinnamon for melon-tinted lips.

A QUICK DO

For a simple but glamorous look, the style team puts Brandi’s hair up in a simple twist and uses a flat iron around the edges for a sleek, clean look.

OUR PANEL

Brandi’s hair
Marissa Schmitt, Studio 110, 110 E. Delaware Pl.; 312-337-6411

Neil’s hair
Brooke Ingram, Studio 110

The brows
Tina Rosado, Studio 110

The makeup
Laura and Chevette Weathersby, dripbook.com/lauraweathersby

The wardrobe
Kate Shifrin, a personal shopper and style consultant; 773-281-5283, kateshifrinstyleconsultants.com.
All clothing was sourced from the 900 Shops, 900 N. Michigan Ave.

Photograph: Lisa Predko