Aureta Thomollari Blogger and president of D&A Luxury Consulting
What stands out: Her collection of vintage designer clothing, obsessively detailed on her fashion blog.
What She's Wearing: Red silk minidress ($5,950) and clutch ($2,195), both by Valentino at Saks Jandel (5510 Wisconsin Ave., Chevy Chase; 301-652-2250). Thomollari is wearing her own black leather slingbacks by Christian Louboutin.
Michael Kahn Artistic director, Shakespeare Theatre Company
What stands out: His recent 30-pound weight loss freed the theater legend’s inner Don Draper.
What He's Wearing: Kahn’s own Façonnable tuxedo, Armani shirt, and Bally shoes; silk-and-rhinestone black tie by Vitaliano Pancaldi, $395 at Saks Fifth Avenue Men’s Store (Mazza Gallerie, 5300 Wisconsin Ave., NW; 202-363-2059).
Kay Kendall Advisory-board member, Washington Ballet
What stands out: Kendall channels the easy glamour of Michelle Pfeiffer.
What she's wearing: Red wool dress by Ports 1961, $476 at Muléh (1831 14th St., NW; 202-667-3440); earrings ($138) and necklace ($75) at Charm Georgetown (2910 M St., NW; 202-298-0420); Valentino pumps, $775 at Neiman Marcus.
Michael Pickrum Chief financial officer, BET Networks
What stands out: Few of Washington’s suit-wearing money guys look this cool.
What he's wearing: Black wool suit by Ermenegildo Zegna ($2,795), white shirt by Giorgio Armani ($225), purple silk tie by Gianluca Isaia ($295), and black silk pocket square ($45), all at Saks Fifth Avenue Men’s Store.
Cheryl New Divorce attorney, New & Lowinger
What stands out: She prefers sleek, minimalist high-fashion separates over standard-issue Ann Taylor suits.
What she's wearing: Beige leather jacket ($3,990) and pants ($3,980) at Saks Jandel; brushed-silver earrings by Paula Mendoza, $300 at Charm Georgetown. Katsuya Fukushima Chef, formerly at José Andrés’s Minibar
What stands out: While his everyday attire is celebrity-chef grunge—red footwear and tattoos—Fukushima has a soft spot for cool designer fashion.
What he's wearing: Black-and-white cotton shirt ($135) and purple silk bow tie ($55) by Saks Fifth Avenue, jeans by 7 for All Mankind ($189), sneakers by Prada ($295), all at Saks Fifth Avenue (Tysons Galleria, McLean; 703-761-0700).
Shirley Gordon Hairstylist/owner, Strands Hair Studios in Wheaton
What stands out: Fearless beauty choices—spiky blond hair one day, auburn tresses the next—and a trendy wardrobe separate her from the typical Washington woman.
What she's wearing: Green jacket ($1,060) and white shirt ($415), both by Junya Watanabe; tweed skirt by Proenza Schouler ($695), all at Hu’s Wear (2906 M St., NW; 202-342-2020). Gordon’s own Christian Louboutin boots.
Johnny Wright Hairstylist to First Lady Michelle Obama and at Immortal Beloved salon
What stands out: The Chicago native favors comfortable clothing by edgy designers to complement his high-voltage personality and schedule.
What he's wearing: Necklaces and bracelet by David Yurman (Tysons Galleria; 703-245-3515). Wright is also wearing a S’exprimer T-shirt, Marc by Marc Jacobs pants, Barneys Co-op jacket, Bally shoes, and Louis Vuitton watch.
Eric Felten Jazz singer and trombonist
What stands out: The swing-style bandleader wears his Humphrey Bogart–like sophistication with natural ease.
What he's wearing: Felten is dressed in his own custom-made ivory double-breasted dinner jacket by Polo Ralph Lauren.
Betsy Lowther Digital strategist, Ogilvy Public Relations Worldwide What stands out: The former fashion editor’s fearless devotion to 1950s-style dressing.
What she's wearing: Abstract-animal-print silk dress by Lanvin, $3,990 at Saks Fifth Avenue (5555 Wisconsin Ave., Chevy Chase; 301-657-9000). Lowther’s own belt, Fragments bracelet, and Diana Broussard shoes.
Shom Chowdhury Management consultant, Navigant Consulting What stands out: The Hindu-goddess tattoos. The 6-percent body fat. The simple-is-sexy uniform. What he's wearing: Chowdhury is wearing his own Prada button-down, Diesel jeans, and Gucci loafers.
Mori Taheripour Managing director, Innovative Health Solutions
What stands out: Taheripour has beauty, brains, and a second job most guys would love—teaching pro athletes business and negotiation skills at the Wharton School of the University of Pennsylvania. What she's wearing: Purple silk one-shoulder dress by Yigal Azrouël, $335 at Saks Fifth Avenue in Chevy Chase.
Joshua Cogan Photographer and videographer What stands out: Cogan combines scruffy informality with a hipster’s laid-back edge.
What he's wearing: Plaid jacket by Etro, $1,445 at Saks Fifth Avenue Men’s Store; white cotton shirt ($125), Levi’s 501 jeans ($98), and cotton plaid tie ($59.50), all at J. Crew.
Naomi Davis Dance instructor and blogger
What stands out: Her va-va-voom sex appeal comes from knowing how to mix modest vintage attire with Bettie Page–style red lipstick and bangs.
What she's wearing: Ivory silk top by Beyond Vintage, $180 at Cusp (3030 M St., NW, 202-625-0893; Tysons Corner Center, McLean, 703-288-1940); gold necklace and ring, both at Charm Georgetown; wool skirt, $118 at J. Crew. Davis’s own J. Crew belt and Steve Madden shoes.
Josh Davis Banking associate What stands out: He takes a banker’s straight-shooter approach to vintage dressing by collecting well-made tweed sport coats, silk ties, and argyle socks.
What he's wearing: Davis is wearing his own clothing: a vintage jacket bought at Meeps (2104 18th St., NW; 202-265-6546), a Charles Tyrwhitt shirt, an Upper French tie, Paper Denim & Cloth jeans, and Allen Edmonds shoes.
Paula Mendoza Jewelry designer
What stands out: The playful, elegant Colombian is the best model for her contemporary creations.
What she's wearing: Black wool dress by Martin Grant, $1,685 at Hu’s Wear; gold necklace ($1,400) and bracelet ($900), both by Paula Mendoza at paulamendoza.com. Mendoza is wearing her own hat.
Branko Boskovic Midfielder, DC United
What stands out: He’s a hot soccer player. Enough said.
What he's wearing: Black leather jacket by Dsquared2 ($1,875) and cotton T-shirt by Diesel ($45), both at Saks Fifth Avenue Men’s Store. Boskovic is wearing his own jeans.
Lindley Thornburg PR consultant, Heather Freeman Media & Public Relations
What stands out: Her girl-next-door demeanor complements a taste for clean-cut American sportswear.
What she's wearing: Printed MicroModal minidress by Torn by Ronny Kobo, $368 at Intermix (3222 M St., NW; 202-298-8080).
Kristin Guiter Public-relations director, Corcoran Gallery of Art
What stands out: Guiter’s enviable collection of cocktail dresses and her glossy black, bobbed hair.
What she's wearing: Sequin-and-feather dress by Badgley Mischka, $715 at Neiman Marcus (Mazza Gallerie, 5300 Wisconsin Ave., NW; 202-966-9700); earrings by Charm Jewelry ($80), bracelet ($310) and crystal ring ($95) by Courtney Lee, all at Charm Georgetown.