Choosing what to wear to work while still expressing your personal style is hard. Throw an after-hours date into the mix and it can feel like an impossible feat. Unless, of course, you have a personal stylist. That’s why we tapped Laurie Brucker, a certified image consultant and stylist, to break down the dreaded desk-to-date outfit debacle.

First things first, versatility is key when it comes to a successful post-work date outfit. “I love when you can take one look or piece and translate it into multiple looks,” Brucker says. “Versatile pieces are ideal for women on-the-go because they allow her to transition seamlessly from one thing to the next.” Depending on your personal style, this could mean a classic little black dress, a power suit, or some high-waisted trousers and a lace-trimmed camisole.

Whatever you choose, there are a few staples Brucker believes every woman should have to make these looks a cinch. “A conversational clutch, a pair of sexy heels, some statement earrings, and your favorite shade of lipstick are all you need to jazz up any work look and shift gears for date night,” she says. Her favorite styling technique, however, is something she calls the “single item switch.” Read on to discover how to transition your outfit from a day at the office to date night.

post-work date outfit


Swap your blazer for a motorcycle jacket

Option one: Switch your sophisticated blazer for a laid-back leather moto jacket. “This will instantly transform your outfit for a more casual, edgier look,” Brucker says, noting that you can layer it with pants or a dress. “Pair with lace-up booties, a fringe clutch, and your bold lip — and you’ll be ready to make an entrance.” 

Above: Blank NYC Suede Moto Jacket ($198;

post-work date outfit


Swap your trousers for skinny jeans

“Half-tuck your blouse, keep the blazer, and add some sexy heels,” Brucker says. Feeling extra feisty? Go for a faux leather or animal-printed pair of skinny jeans. 

Above: Liverpool Jeans Abby Highwaist Ankle Skinny Jeans ($98;

post-work date outfit


Swap your blouse for a silk camisole

A lacy silk camisole can be layered under a serious blazer to bring some boudoir-inspired sizzle. Wear it under your blouse during the day, and then on its own at night. 

Above: Cami NYC The Racer Top ($148;

post-work date outfit

Swap your sweater for a denim jacket

Ditch the cardigan for date night. A denim jacket instantly makes an office appropriate outfit more casual. It even works over a suit, Brucker adds.

Above: ELOQUII Boyfriend Denim Trucker Jacket ($100;

post-work date outfit

Swap your pumps for statement booties

Slip out of your work heels or commuting flats and into a pair of chic booties to instantly step up your look. Brucker suggests a sexy lace-up pair for date night.

Above: Archive Shoes The Delancey Boot in Eggshell ($258;

Want more ideas?

Keep scrolling for some desk-to-date fashion essentials to make your next post-work date outfit a breeze to style.