1. AFTERNOON CARPOOL
Stay-at-home mother Angela Walters, 37, left, needed to be convinced of khaki's coolness: "There's that stigma," she says. "You know, the mom in the khakis—I don't want to be that!" But these inventive tuxedo pants (Gap, $50), worn with a ribbon for a belt, are "a more stylish take" on chinos, she says. "I'd also wear them with Converse sneakers and a tank top."
Tee, Lands' End, $15. Wedges, Charles by Charles David.
"As far as I'm concerned, khakis should be the bread and butter of the closet," says 44-year-old sales executive Laurie Arron, right. A mix of trouser khakis (Banana Republic, $79), a bright trench (Burberry London, $795), a button-down shirt (Tory Burch, $210), and flats (Manolo Blahnik) works for both interior design scouting with her 3-year-old twins and an early alfresco dinner with her husband.
Hoops, Ten Thousand Things. Bracelets, Robert Lee Morris and Ted Rossi. Bag, MZ Wallace.
2. DATE NIGHT
"I never thought of khakis for evening," says 44-year-old children's clothing designer Iben Dismond, who wears the cheapest jeans she can find to her kids' playground by day and upgrades to fitted, cropped denim and heels at night. Here, she goes for a pair of rolled-up boyfriend khakis (Banana Republic, $70) with a sequined top (Gryphon New York, $365) and gladiator sandals (Giuseppe Zanotti Design). "This is how to do khaki—turn it into something special," says Iben.
Hoops and cuff, Robert Lee Morris. Ring, Ben-Amun by Isaac Manevitz. Clutch, VBH.
3. STAYING IN
"I've never been a khaki girl," admits Sandi Bass, left, who—still enviably lithe at 60—has always stuck to jeans or leggings. Now she's discovered that slim, cropped khakis (Loft, $60) feel lighter and easier for summer, especially paired with a peasant blouse (Ralph Lauren Blue Label, $345) and simple flats (All Black). "They're so comfy," says Sandi, "they'll help me get where I'm going a little bit faster"—like from her job as a model scout to daughter Christina's house to watch her grandchildren (Malea, 2, left, and Naima, 14 months).
Shell, Ralph Lauren Blue Label, $68
GIRLS' NIGHT OUT
Christina Copeland, a 29-year-old actress, right, steps out in a pair of cuffed cargo pants (Tommy Hilfiger, $68), a graphic blouse (Yigal Azrouël, $410), and platform wedges (Christian Louboutin). "This outfit is classy and funky," says Christina, who finds it a few notches above her usual jeans and tees. "I like it!"
Earrings, Gara Danielle. Bracelets, Gara Danielle and Diane Cotton Jewelry. On Malea: Dress, Ralph Lauren Childrenswear, $55. Shoes, Simple Shoes. On Naima: Onesie, Petit Bateau, $20. Roll-up pants, BabyGap, $20. Shoes, Converse.
4. WORKDAY MEETING
"I have a full figure, and I like to accentuate that," says Rose Donato, 53, a global project manager. Slim trousers (Talbots, $80), paired with a slightly darker safari-inspired shirt-jacket (Outback Red by The Limited, $60), emphasize her waist and lengthen her 51 frame without being too matchy. A leopard-print bag (Kotur) and studded sandals (Jinny Kim) give the outfit an edge while keeping it office-friendly. "I love animal prints," Rose says. "Especially with khaki, they just add a little drama."
Earrings, Noir. Bangle, Alexis Bittar. Ring, Gara Danielle.
5. WEEKEND BARBECUE
"I try to stay away from jeans. They're either too tight or too loose," says devoted khaki wearer Danimaris Fonseca, 28, a systems administrator. On relaxed weekends, cropped khakis with a cuff (Not Your Daughter's Jeans, $98) add just enough structure to a beachy tunic (Chico's, $89) to take her from the farmers' market to an afternoon barbecue with friends. The stretch sateen pants cinch Danimaris's curvy midsection. Capri-length bottoms always look best with a bit of a heel (wedges, Coach). Bangles, Ben-Amun by Isaac Manevitz.See more of the summer's most wearable trends, modeled by actress-comedian-mom Ali Wentworth