by Renae Virata
We received a question from one reader that we were totally all over: I’m going to dinner with my boyfriend, his boss, and the boss’ new wife. What do I wear?! When my boyfriend mentioned dress code to the boss he said, “Business casual or casual.” I’ll be flying in and going right to dinner so I’ll need something to last on the plane. Help!?
Between the business talk and getting-to-know-you chit-chat, things like what you are wearing can speak more loudly about who you are in those two or three hours you are together. Whether you are the employee or “the date,” it’s important to let your clothes say just the right thing in this special one-on-one (on-one-on-one) situation.
Admit it: You’re already a teensy bit nervous, right? So the first thing when deciding what to wear is to make sure you’re comfortable. For the sake of simplicity, go with an outfit that you know you not only look great it in but that has been tested for comfort (i.e. nothing pulling, bunching, too tight, or in need of repair). Second, choose something that is not too loud. A skirt and blouse combo with a jacket or cardigan will work just as well as a simple dress in a solid color or non-distracting print. Third, if the boss said business casual or casual, err on the side of business casual. That usually means what you’d wear on a day you don’t have a meeting and also means…no jeans!
Part of the impression you leave is also about your individuality, so don’t hesitate to wear one fun piece or element in your outfit. It can make for a great conversation-starter, too! A fun antique brooch that your grandmother gave you, your favorite ankle boots worn with tights (now, that’s a fashion statement!), or a blouse with an interesting detail like a few ruffles or a cool print will add stylish confidence and keep positive attention on you, too.
In regards to hopping off a plane straight to dinner (which I’ve personally done many times), your best bet is to wear either a knee-length jersey wrap dress in a darker color, just in case something gets spilled on you en route, or a pair of black pants with a cute blouse and non-matching jacket. On your feet: Wedge boots are more comfortable and easier to slip off and on in the security line or a pair of sturdy heels in a fun color. But leave the stilettos at home. You can also wear a pair of flats that you can easily slip back into your carry-on when after you make a shoe-switch before dinner. Make sure you wear tights or sheer hose to, again, err on the conservative.
Here are a few examples we put together for a great polished but relaxed (read: business casual) outfit. Good luck!
Click on an item to learn more and to shop the look: Isabella Oliver Jacket $285, Esprit Blouse $59.50, French Connection Skirt $98, Kendall Bootie $139.99
Add a light scarf artfully draped around your neck and black ribbed tights for a warm, put-together look.
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Click on an item to learn more and to shop this look: French Connection Dress $98, Isabella Oliver $99, Merrell $174.99, Tolani Scarf $76
Luxurious yet practical, this outfit is just the right amount of polish and relaxed. Get a pop of color from the fun scarf (drape loosely or loop through for a more cozy look). Wrinkle-free and comfortable for the plane.
Click on an item to learn more and to shop this look: Isabella Oliver Jacket $529, Esprit Blouse $59.50, Esprit Trousers $129.50, Carlos Santana Heels $89
Tough but chic – who wouldn’t feel confident in this lethal combo?






