Why Being Overdressed Shouldn't Be A Bad Thing

by Naomi Nishihara

Between our parents, our friends, and our co-workers, we hear a lot of conflicting advice about how to dress. We dispute appropriateness, quality vs. trendiness, what should be wardrobe staples, etc. But no matter where you stand on either side of the argument, you've probably wondered how to not look overdressed — because for many, there's nothing worse than showing up to a party wearing a full face of makeup and a beaded maxi, when everyone else is wearing jeans and beanies. Harumph.

Many people stand by the classic advice that you never want to look like you tried too hard. Others agree with the popular Oscar Wilde quote, “You can never be overdressed or overeducated.” It’s easy to worry about overdressing, because for many, myself included, looking casual is a way of lowering the stakes. An event doesn’t have to go perfectly if it seems like you didn’t plan too much in advance. Your next date doesn’t have to be amazing if you didn’t care enough to spend time getting ready. But I'm here to defend the act of dressing up, because I believe that there’s a possibility that spending some extra time getting ready can make an experience better.

Your mood before you go on a date or to a party can influence how the evening goes. Naturally, if you’re in a bad mood, you’re less likely to enjoy yourself. But if you take the time to pick a great outfit and do your hair just the way you like it, you mentally prepare yourself more for a fun or eventful evening.

Sure, this isn’t always the case. You should never try to outshine a bride at her wedding, and it’s inadvisable to wear something impractical, no matter how cute, if you’re going to the gym. But barring inappropriateness, here are six situations you should never be afraid to dress up for.

When You’re At Work

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We hear things like “Dress for the job you want, not the job you have,” all the time. When it comes to your career, ability and professionalism should matter much more than personal style. But attitude is a big part of professionalism, and how you dress is one of the best ways to show that you care about your work.

Even if your co-workers wear jeans and sweatshirts to work everyday doesn't mean you can't make an extra effort to care about what you're wearing. If your office is pretty casual, you don’t need to dress like a banker, but taking the extra five minutes in the morning to whip together something that you'd be proud to Instagram as your #OOTD makes a huge difference in your mood.

When You’re At School

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When I was in college, I was one of those students who liked to attend office hours. I was an English major, so meetings with professors were conversational (and sometimes we would even gossip!). Over the years, a few mentioned that they always noticed which students wore pajamas to class, which surprised me. It might seem silly to get up early and put on a pair of pants when you have an 8 a.m. lecture, but bear in mind that some professors are definitely paying attention. How you present yourself in class or lecture can sometimes be the difference between whether or not your teacher thinks you care.

When You’re Out With Friends

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It's no surprise — whether it's a glamorous girls night or happy hour with your best friend, chances are you'll have a better time if you love what you're wearing or if you're having a good makeup/hair day. Even if you’re going out to a divey bar where you can’t really see what anyone else is wear anyway, you’ll still be more excited to be there if you're stoked about your ensemble.

One side note: When you’re out with friends, it’s much more exciting to dress up if everyone else dresses up, too. Send a few texts before you leave home encouraging everyone else to look their best.

When You’re On A Date

This one seems self-explanatory, but just in case: If you put little effort into outfit planning or don't love what you're wearing to a date, you might just convince yourself that you don't really care about the date at all either. Even if you’re going to dinner with someone you’ve been with for a long time, dressing up is still a visible reminder that you care and a fun way to keep things exciting.

When You’re At A Family Gathering


Family is forever, which means they’ve known you as a baby, through your awkward phase and everything in between. Dressing up for family gatherings seems unnecessary because these are people who you don’t need to impress. But it’s also a nice way to help them see you as an adult. To be clear, I’m definitely not recommending your flashiest little black dress, but putting some thought into your outfit can make the difference between looking like you have your life together and looking like the high schooler you were not too long ago.

When You’re Out On Your Own

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I’m a huge fan of going places alone — whether it’s shopping, to a coffee shop, or just walking through downtown. Why? Because it’s the perfect time to test out new outfits. Sometimes, walking back and forth in front of your mirror doesn’t give you enough information to know if an outfit is as great as you think it is. Wind might be an issue with a new skirt, while a new pair of heels won't really prove how uncomfortable they can be until you give them a real test run.

Another reasons you should never care about being "too dressed up?" A former roommate used to always tell me, you never know who you’re going to meet, so why not try to look nice? At the very least, it's a great excuse to go shopping.

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