I’m faced with choosing between looking a bit tarty at the office or a bit frumpy at my post-work event of the day. I usually choose the former. I’ll do anything not to look frumpy. Really though: what can you wear that’s appropriate for a business casual environment that’s also appropriate to interview a former supermodel for instance? —Andrea, New York

Finding an outfit that can transition from the office to a nighttime event isn’t as tricky as you think. It’s all about layering and accessorizing. I’ve created four day-to-night outfits using four versatile items from my wardrobe: a pencil skirt, jumpsuit, shift dress and sparkly top.

Look #1: The Pencil Skirt
Pencil skirts are sexy enough to wear at night, yet still appropriate for day when you’re dressed conservatively up top. For the office, I’ve covered a cami with a button-down shirt. I’ve also worn my necklace as a bracelet to avoid looking too sparkly at work. Before leaving for an event, I could take off the top layer and add the necklace.
Karen Millen skirt, Theory button-down, Jimmy Choo sandals, Etro tank, lia sophia necklace

Look #2: The Jumpsuit
Cardigans are your best friend when it comes to transitional dressing. Here, I’ve belted my cardigan to disguise the plunging neckline of my jumpsuit. It looks like I’m wearing a wide-leg pant. For night, I’ve turned my necklace into a bracelet to show off the dramatic cut.
Forever 21 jumpsuit, Forever 21 cardigan, Bebe belt, vintage pearls, Prada pumps

Look #3: The Shift Dress
Shift dresses are the easiest way to go from the office to an event. Wear flats to work but store a sexy pair of heels in your drawer to slip into later. A brooch makes the dress more business-like while a gold belt and bling bracelet prepare you for cocktails.
Moon Katz dress, vintage brooch, London Sole ballet flats vintage belt, Moschino Cheap & Chic sandals, lia sophia bracelet

Look #4: Statement Top
A blazer instantly polishes an outfit. For work, I’ve buttoned my jacket so only a slip of my bright top pokes through. For night, I’d unbutton it and roll up the sleeves—or just leave the blazer at my desk and bring it home it the next day.
Plenty by Tracey Reese top, Forever 21 pants, Theory blazer, Prada pumps, Ritmo Mvndo watch

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