Is It Better to Be Overdressed or Underdressed?

There are many great debates these days: Coke vs. Pepsi, city life vs. country, Bieber vs. Kardashian (as in who would you rather never see on TV again).  But as a manners guru, a top issue that seems to often come my way is the quandary of being overdressed vs. underdressed.  It comes down to the underlying question, “Will I look out of place by wearing this?” Sure you want to be noticed for the effort you put into your outfit, but you also don’t want to be judged unfairly if you miscalculate.  

Here’s a very typical scenario: You get invited to a dinner party at a friend’s house, but they don’t specify a dress code for the evening. So, with 10 minutes remaining before you have to leave you waver back and forth like a game of Apparel Ping Pong, deciding whether to wear a jacket or just a shirt, nice jeans or dress pants, flats or boots. Finally you leave the house wondering if you’ll be complimented or ridiculed for your choices. Is it better to be overdressed or underdressed? 

Personally, I happen to be a huge fan of fashion. I love to look nice whenever I leave the house. To me, clothing is art and as with art, everyone has their own opinion on what works and what doesn’t. However, what is proper is another issue.  Proper dress code doesn’t come down to how expensive something is, just that it works for the occassion. Even though I follow the rule of “to each his own,” looking the right way for an event is more than simply a personal choice. Proper attire says a lot about a person. For one, it says you are a mature adult who understands social norms and secondly (most importantly) it shows that you respect your host enough to dress the part.

Regardless whether it’s a backyard BBQ, a toddler’s birthday party, an office happy hour, or a wedding, there are certain near-universal expectations of what is appropriate. So when in doubt, always dress for the occasion. And if you’re not sure, leave yourself some options. Here’s how:

Tip #1: Dressy Events

For dressy events like a wedding, there is no such thing as being overdressed – unless you plan on wearing a wedding gown as a guest. That’s tacky (as is wearing any white dress – the bride should be the only one in white on that occasion). For men, tuxedos are standard, and if you are the only one wearing one, you can still blend in. If you don’t have a tuxedo, a nice suit is also appropriate.  There is not much wiggle room on this. Every man should own a suit, period! And that one suit should be able to be worn at a wedding and a job interview. 

As for the ladies, if you feel your gown is too elaborate or revealing, I recommend bringing a shawl to cover your shoulders or part of your dress for a more modest touch. A shawl complements any dress and if you invest in a nice neutral-colored one, you can wear it on many different occasions. A shawl is also easy to carry and a handy accessory that can be taken on or off very easily to adjust to the particular setting. 

Tip #2: Keepin’ it Casual…But Classy

For most of us, the big issue isn’t going to be deciding what to wear to a wedding. No, it’s deciding how to dress in more casual, everyday settings. The best solution – for both men and women – is a blazer. And not the stuffy, boxy one that my mom made me wear at my bar mitzvah. I’m talking about your official “party blazer.” Yes, folks, there is such a thing.  It’s usually a solid-colored, well-fitted jacket that can be worn with almost anything – jeans, pants, skirts, dresses, etc. 

A good blazer has the ability to transform any outfit instantly. Wear it with jeans for a casual but classy style. And if you feel overdressed, you can take the jacket off and become instantly casual. If you feel underdressed, you can add your secret weapon – a pocket square for the guys and a light scarf for the ladies. The pocket square and scarf are slick accent pieces that ramp up the style quotient of any outfit.

In the end, if have doubts as to what a wear, it’s best to err on the side of classy, rather than casual. You’ll win more points for looking sharp than looking drab.  

Woman in dressing room and man in blazer images courtesy of Shutterstock.