From Work, to Working It: Outfits that Go from “Day” to “Play”

By Erin Donnelly

You’re a single woman with an active social life—dates, pow-wows with the girls, and countless other extracurricular activities. But that doesn’t mean you’re slacking off in the career department. Though you’d love to have time to soak in a bathtub and try on every outfit in your closet before heading out again for the evening, the reality of your busy schedule means frantically dousing yourself in perfume and adding a fresh coat of lip gloss in the ladies’ room at work while praying that your pant suit doesn’t look too lame in a bar full of sexy singles.
Perhaps we can suggest a different approach. All a single woman needs to go from “work” to “working it” are a few strategic outfits that can be glammed out or suited up as the situation calls for it. A few choice accessories stashed in your bottom desk drawer will make the day to play transition complete. No more strutting around the office in scandalous knee-high stilettos, no more lugging supersized gym bags packed with a change of clothes, and no more dowdy date night outfits when your meeting runs late. Just don’t forget to take off your office security ID badge—that creep trying to buy you a drink doesn’t need to know your name.  
Black Halo Silk Chiffon & Tweed Dress
Who says tweed can’t be sexy? This frilly cami/tweed pencil skirt combo oozes a 1940s pin-up vibe that’s ideal for a woman with below-the-belt curves. A cropped black or gray pinstriped blazer with a cinched waist makes it workplace-ready and takes the edge off the ultra-feminine top. When you’re ready to go out, lose the jacket and add red patent platform heels and some bracelets to become a va-va-voom vixen. 
Norma Kamali Timeless All-in-One Short Dress
Norma Kamali deserves a medal for her genius, stress-saving collection of convertible garments, which can be easily transformed into a number of different styles. Her All-In-One Short Dress for Spiegel is the perfect work-to-play piece. By day, the knee-length dress can be worn to show off its sophisticated boatneck collar and drapey dolman-style sleeves.
Come nightfall, a quick readjustment can turn the dress into a sexy one-shoulder gown or halter dress that’s ready to paint the town red; it can also be paired with Norma Kamali’s other convertible garments to create more options, like a long tube dress. Amp up your accessories by swapping your sturdy briefcase for a glamorous clutch, and adding strappy metallic heels and dangling chandelier earrings. Nobody will have a clue that you’ve been pushing paperwork in the exact same dress all day—and that’s the point.
What’s more, the All-in-One Short Dress is as versatile color-wise as it is design-wise. Choose from black, bitter chocolate, steel, taupe, dark red, purple ink, and more.
Isabel & Nina Coachmen Pant Suit
A corporate ladder-climbing gal like you can’t stray too far from a power suit. Unfortunately, that means that the dates you meet after work often think you’re there to audit them, not flirt. Still, if you can’t lose the suit, there are plenty of ways to make it more chic and less pencil-pusher. Of course, it helps to start with a suit that boasts a figure-flattering cut and modern details, like this empire-waisted version from Isabel & Nina. Though it’s tasteful and sophisticated enough to make you a commanding presence in the boardroom, the suit’s fashionable design can easily hold its on own outside of the office.
Your nighttime transition: Ditch the blazer and replace it with a going out top, like this floaty Express Volume Sleeve Crop Top. The pants are hip and curve-hugging enough to work in the club (or wherever the evening takes you).  
Mara Hoffman Taupe Full Sleeve Lady Dress
A wrap dress is the working woman’s best friend—it’s figure-flattering, comfortable, effortlessly chic, and can easily be glammed up when your last meeting of the day drags on forever, leaving you zero time to primp before meeting your date. The irresistibly touchable (hint, hint) silk jersey fabric of this Mara Hoffman version adds a luxe finish, while the loose dolman sleeves and plunging neckline look modern and the appropriate amount of seductive. But if you’re worried that a glimpse of cleavage might send your senior partner into cardiac arrest, slip on a delicate white or off-white cami underneath. Less is more, after all, and you can always lose the cami later on before meeting Mr. Maybe Wrong But Definitely Handsome. This dress calls for a black envelope clutch and heels in the pm, with hair that’s worn down and hammered gold earrings.
Now, about those running shoes you’ve been wearing with your suit during your morning commute…

An Online Primer on Accessorizing…
SMW’s Whitney and Wyatt have created a fabulous video on how to accessorize.  Click here to see it.


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