Balancing your work and social lives can be a hassle. Our daily schedules are often tight and leave little transition time between the workplace and our evening plans––plans that might even include a date with a significant other. But there’s a better way to go from workday to date night than running home and frantically trying to piece together a new look from scratch. The outfit you wear to work can be stylish, comfortable, and more than appropriate for an evening date.


More casual attire is becoming increasingly accepted in the workplace. So, next time you hop from boardroom to boardwalk, ditch the pantsuit and try some of these work-to-date ideas instead.

Make a Casual Dress Classy 

A dress that makes you feel cute and comfy is always the right choice. To keep it casual, try a relaxed t-shirt dress. You can amp up the professional look by adding a blazer or another tailored jacket. It can always be swapped out later in the evening for a denim or leather number or even a military-style jacket. Even a mini-dress can be made appropriate for work if you pair it with some tights or leggings. The convenient thing about these is that you can remove them later to show off some extra leg for your date.


  • Extra Tip: Ankle boots are perfect for any dress length, and they are as practical as they are professional.

Pair a Button Down and Dark Jeans

Nothing is as universally flattering as a buttoned blouse and dark-wash jeans. A button-down is the perfect transition piece. At work, you can keep the buttons up high and modest while tucking in the hem. For date night, unbutton two or three buttons (or however many you’re comfortable with) to show some skin. To relax the look a bit more, keep it untucked and scrunch up the sleeves. Pairing this with black heels will make you a total knockout.


  • Extra Tip: Though more workplaces allow jeans these days, you can also swap them out for black slacks or a dark midi skirt. Something straight down or form-fitting is best to balance out the looser fabric of the shirt.

Save Your Bottom Layer for Later

Another spin on the button-down method is wearing a fitted tank top underneath a shirt or blouse. Keep it buttoned, or mostly buttoned, at work. When it’s time to hit the town, unbutton the shirt completely to show off the top underneath. Leave it hanging loosely like a jacket, or tie the ends of the shirt around your waist to create a cinching effect. Alternatively, shed the shirt completely and show off your shoulders.


  • Extra Tip: A more chic alternative to the tank top is a silk or satin camisole; one with a bit of lace on the hem is feminine and charming.

Make a Statement With Your Outer Layer

While wearing your date outfit underneath your professional layer is one way to go, sometimes you can begin with a businesslike base and step up your style in the evening with your best piece on top. A plain black dress, or a blouse and slacks, can make an excellent canvas for a statement jacket that you throw on later. Make it cool and comfy––like an oversized sherpa fleece––or bright and flashy––like a holographic bomber jacket. This outfit choice may be bold, but so are you.


  • Extra Tip: Add some earrings for an extra pop of color and complete the look from head to toe.

Spruce Any Outfit With a Blazer

After a long day of work and a date coming up after, what you really might be looking for is something comfortable. In that case, there’s no reason you can’t switch out the button-down for a soft, breathable shirt instead. If the shirt on its own feels too casual, a blazer is all you need to bring it up to workplace chic. To get these two pieces working together, roll the sleeves of the blazer up just slightly. Pair this with curve-hugging pants for practicality and allure. After work, ditch the blazer for a motorcycle jacket––or none at all––and you’ll be good to go.


  • Extra Tip: A polished pair of loafers or two-toned oxford shoes are a cute addition to this look, as they are stylish yet practical.

Show Off Your Figure in a Turtleneck 

Nothing says sophistication like a nicely fitted turtleneck––and nothing says comfort quite like one either. A snug turtleneck is a great way to cover up and remain work-appropriate––not to mention warm––while still flattering your figure and showing off some curves. Draping a black or brown leather jacket over the top brings this further into that classic trendy autumnal look.


  • Extra Tip: Add boots with a slight heel and you’ll turn heads in and outside of the office.

A Midi Dress Is Always Appropriate 

Perhaps a shirt and slacks feels a bit too slick for you, and you’d like something more on the breezy, romantic side. In that case, you can’t go wrong with a midi-dress. This kind of dress typically ends just below the knee, making it perfectly office-appropriate while adding a touch of femininity. While at work, you may want to pair the midi-dress with a slight heel; for the date night, however, you can keep it easy and ground the look a bit more by swapping out the heels for sneakers. If you have no plans of taking off your sweater, a mini-skirt is great, too.


  • Extra Tip: Platform white sneakers are a great look with a midi-dress because they complement most colors and give the legs a slightly elongated effect.  

Pair a Crop Top With Highwaisted Bottoms 

Rocking a crop top at work might seem risky unless you’re a lifeguard or a belly dancer. But in a more casual work environment, there is a method to get away with it. Simply wear bottoms that have a waistband high enough to reach your belly button (or wherever the hem of the crop top is) to avoid having skin peek through. If you’re able to pair this with a belt and tuck the crop top in, even better––now you’re creating an hourglass shape. Add a chic layer––like a cardigan or boxy tweed jacket––to finish off the look. After work, simply shed the layer and flaunt your figure.


  • Extra Tip: Pants that flare out at the bottom are a fun way to turn this into a retro look as well.

Use Accessories To Go From Dapper to Glam 

Sometimes, all you need to bring your outfit to the next level is a few key accessories. Wear your usual work outfit, but keep a couple of pieces handy for later: Think your favorite lipstick, necklace, and heels. You can always swap out a backpack or briefcase for a stylish clutch purse. These are very simple and subtle additions that can nevertheless change the whole impression of the look.


  • Extra Tip: Just remember not to go overboard. Limit yourself to one piece that draws the eye, and others that simply complement it.

Overall, the best thing to keep in mind when styling transition pieces for work and date night is leaving room to mix and match. Even workplace guidelines can’t stop your style from shining. Simply swapping out one layer or accessory for another can change the entire nature of a look. Blazers can be ditched for bombers, and kitten heels can be hung up for sneakers. Which combinations you come up with depends ultimately on your taste and, of course, the date-night activity.


So whether you’re heading to a fancy dinner or a drive-in movie, don’t get stressed about your outfit. We hope these tips give you some style inspiration.



How a Casual Dress Code Can Help Attract Top Talent | Indeed

Not Just Fridays: More Companies Embrace Casual Dress Codes | NPR

Professional Appearance in the Workplace | Simply Hired