Oscar Wilde’s quote, “You can never be overdressed or overeducated,” is frequently used to justify being dressed up for ordinary occasions, but is it true? It depends on the situation, and I would rather be overdressed than underdressed.
Overall, people tend to dress more casually than they used to, but dressing down is okay in some places, like the workplace. Most companies are trending away from formal business attire, and I think that’s a good thing.
However, I think it has gotten to the point where people are okay with disregarding dress codes, which bothers me. On Friday, I was at the restaurant that stated a business casual dress code on their website, yet there were young women in clubbing dresses and men in ripped jeans. I also saw many pairs of jeans shorts when I was at a more formal event last month. I feel like dressing up is part of the fun of those situations, and at the very least, following the dress code is respectful.
At worst, being overdressed is sticking out (in a good way). It demonstrates that you made an effort, which shows respect. Underdressed at worst, comes off as sticking out, poor social awareness, AND not entirely giving a shit. Keep in mind that casual vs. formal is not the same as caring vs. uncaring in your appearance – you can definitely look polished and put together in a pair of jeans and a shirt, and you can look sloppy and awkward in a business suit.
The difference is that most people feel very uncomfortable when they’re obviously overdressed, as it’s probably not what they usually wear. Being over or underdressed and the obvious accompanying discomfort will make you stick out even more.
My philosophy is that overdressed can almost always be easily dressed down when you’re out if you’re really out of place (remove a jacket, take off your tie, or untuck a shirt). But you can’t dress up if you’re underdressed without having to buy something while you’re out. What options do you have if you arrive wearing shorts and flip-flops?
Never fear! You can still be stylish and up your game in every situation but not be overly dressed or overly styled. Perhaps you don’t want to look like you went on a limb or tried something a little bit extra — looking appropriate given any situation or peer group while still maintaining a degree of elevated style is absolutely possible.
My personal belief is it is absolutely always better to be overdressed than under-dressed.
Okay, so you’re heading out to a bar to hang out with the boys, and you know it’s the relaxed fit jeans + boxy t-shirts + running shoes standard dress. No problem. You will choose to wear jeans that fit, a t-shirt that is more fitted & tailored, and fashion sneakers. My choice is minimal white leather sneakers.
Even though your buddies may give you a hard time, it’s because they’re secretly a bit envious. The next time they meet you, they’re probably going to step up their game as well. As your style increases, their style will start to increase.
The gist is that you’re still fitting into the social culture and within the confines of your peer group, but at the same time, elevating your own style to the next level. You can do this for any situation, whether for pleasure or work.
Your wife or significant other may also give you a hard time. They may ask, “Is that what you’re wearing?” and after you confirm, a lot of times, they will put on something else. They won’t make you change, however. You see, a lot of times I get dressed-up even if I go out to dinner to a pizza place. I might wear a nice pair of driving moccasins and a fitted button-down, and depending on my mood, I may dress even nicer.
What happens when you don’t know the place or people — how can you still be a little bit overdressed and a little bit more stylized than the other men? When you aren’t sure what the level of dress is for a place you’re going to, ask. Then, choose basics and layer. Keep your outfit simple with neutral colors.
Get people to look at you for the right reasons. Don’t hesitate to step up your game throughout your work week and still fit into your group. Your efforts will also make your wife or significant other happy to boot. Remember, overdressing does have a limit. If you want to dress up in a three-piece suit and go hang out with the boys at the bar, that’s a bit overdressed and excessive. So, my friend, dress up. It’s okay! Just make sure that your clothes fit properly and that they are tastefully stylish.
