HOLLY PENIKAS > 29
> Author of the style blog covetouscreatures.com, Penikas is a creative dresser. You’d never know she was wearing a sexy black Emily Ryan minidress under this bright yellow parachute-inspired skirt (by local designer Emily Muller). Stepping out of the skirt, Penikas goes from artsy to va-va-voom in seconds.
> Though slim and chic, Penikas is petite at just 5 feet tall, so the long charm necklace (from the gift shop at the Fairmont Copley Plaza) emphasizes the vertical and gives her the illusion of more height.
> Sure, Penikas could wear black heels, but they wouldn’t make the bold personal statement she gets from these funky Jeffrey Campbell lace-up booties from Thom Brown.
FAVORITE STORES: Stel’s, Rescue (“for designer pieces I couldn’t otherwise afford”), and Artifaktori
FARRELL MCCLERNON > 24
> Though a black coat would have been dressier, the elegant brown tweed has a softness and timeless appeal that really works with the outfit. The top-of-the-line Ralph Lauren classic was a castoff from a woman for whom McClernon baby-sat.
> It’s a gutsy choice to pair a sheer blue top (from LF on Newbury Street) with a bold orange skirt, but McClernon pulls it off. By tying the blouse instead of tucking it in, she echoes the vintage vibe of the skirt.
> The skirt’s tight silhouette and length may be classic ’50s (think Rizzo in Grease), but the neon orange color definitely says modern.
> To complete the head-to-toe retro feel, McClernon went with high-heeled Mary Janes. “We have a liberal work dress code,” explains the account manager at a technology start-up.
FAVORITE STORES: LF, TJ Maxx, AllSaints, and Anthropologie
NAJEEMA HOLAS-HUGGINS > 28
> The white shirt is like sherbet at a fancy meal — call it a palette cleanser. (It’s a J.Crew classic that Holas-Huggins got at a clothing swap hosted by theswapaholics.com.) “There’s only so much my boss will let me get away with,” says the marketing manager at a nonprofit agency.
> The bright-orange scarf (made in India and a gift from Mom) draws the eye, balancing the bold print on the bottom.
> Holas-Huggins’s Tory Burch splatter-print pants (she scored them on eBay) would be a cool focal point for any outfit, looking mod or boho depending on the top.
> Boring black shoes would kill the look. Holas goes for another color pop instead with these hip Jeffrey Campbell red heels from TJ Maxx.
FAVORITE STORES: Forever 21 for fun jewelry, H&M, and Zara