What do I wear if I am eating with…?

[This is a version of an article that I didn't publish in print, but wanted to share :)]
What do I wear if I am eating with…? Don’t worry. Even born and bred New Yorkers don’t always know how to dress in general, but this guide will give you the know how to dress to a T when dining out. Whether you are dressing for a hot first date, meeting your significant others or roommates’ parents for the first time, or discussing derivative strategy with your internship boss over a business dinner, we’ve got you covered.

First date

First dates can be super awkward and nerve wracking, so make sure that whatever you are wearing, you are comfortable so you can focus on your date. If you are stressing over potential allergies to your new tie that may or may not develop into hives around your neck or that your new top doesn’t fit exactly right, you probably aren’t going to feel relaxed. No matter what, be yourself! Dress in a way that expresses yourself by adding your favorite pieces of jewelry or sneakers.

Failure to Launch (2006), Sarah Jessica Parker (Paula) and Matthew McConaughey (Tripp)

Guys: Guys should wear a solid or thinly-striped button up with jeans like Matthew McConaughey in Failure to Launch. If the restaurant you are going to is super casual, go for the classic jeans and a t-shirt. Wear any shoe except a flip-flop because it might seem too casual and some people hate feet! Add sophistication to your outfit with a cool watch.

Girls: Frankly ladies, if you are looking for a partner who is long term, cover up a little! Dress for respect. You can still show off that hot body, but do it by wearing a form fitting dress that only shows a hint of cleavage and covers the mid-thigh, like Sarah Jessica Parker. If dresses don’t suit you, aim for a sparkly tank, fitted blazer, and dark wash jeans with flats.

Meeting the Parents

First dates might be awkward, but meeting the parents is another whole ball game! You will only see your significant other or roommates’ parents once in a blue, but you will never hear the end of it if the parents decide they don’t like you, as was the problem in the case of Greg Focker in Meet the Parents. At least what Greg did do right was dress in a non-confrontational and casual way (entirely opposite of Pam’s crazy dad’s attitude)

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Meet the Parents (2000), Ben Stiller (Greg) and Teri Polo (Pam)        

Guys: All parents are different, so the keys to ‘meet the parents’ dress are to avoid wearing logos and cover up the tats that mom and dad might not approve of (shameful finger wag!). Needless to say, a long sleeve v-neck with beige bermuda shorts and your favorite loafers is a safe outfit because you can always roll up or down the sleeves and still feel comfortable when you are being grilled by ‘Mr. Byrnes’ about your intentions with their daughter!

Girls: Cover up the boobs, butt, and legs, and skip the heels! You might not be going to church, but you are not trying to get the dad or the mother to think anything badly of you! Pam dressed like a girl who a guy would be happy to take home to mom by creating a casual, but non-exposing outfit. Match straight leg jeans with a conservative tank, colorful cardigan, and those fun sandals hiding in the back of your closet.

Dinner with Employer

Usually, if you are going out to dinner with an employer, you will be leaving straight from work, meaning you will have no time to change, so don’t worry about changing out of your outfit. However, the tricks to wearing ‘dinner with employer’ appropriate clothing are layers and stashing some ‘musts’ in your work bag. No matter what, your outfit should stay professional and formal if the nature of the dinner is going to stay professional and formal. Even though the sexual tension between Andrew and Margaret made their work relationship totally inappropriate in The Proposal, their work wear was entirely apt for every professional occasion.

The Proposal (2009), Ryan Reynolds (Andrew) and Sandra Bullock (Margaret)

Guys: Ryan Reynold’s character, Andrew, shouldn’t have let Sandra Bullock’s character, Margaret, push him around so much. But, his outfit was spot-on. Wear a navy or black fitted suit with a simple long sleeve button-up and dark, leather shoes is a sure-fire way to stay formal, but still have the lee-way to take off your jacket and tie in case you get hot.

Girls: If you know you have a business-related dinner after work, wear a capped-sleeve print dress with a colorful, fitted blazer and solid-colored, pointy-toe heels. You can take off the blazer if you get hot and still keep the nature of your meeting over food professional because your shoulders are covered up. To make your outfit more fun, stash sparkly, statement pieces like dangly earrings or a long necklace in your purse to maybe get the attention of your cute waiter.

TIP: Make sure that you are familiar with the formality of dress wherever you are eating is that you don’t feel over or under dressed. A good general rule of thumb is to keep it covered in any of the three circumstances because they are all a bit more formal than eating in your pajamas or going out to a club.