Point/Counterpoint: Should you overdress 
or underdress?

Point: Overdressed Is Best

Whether you’re overdressed or underdressed, you’re going to stick out like a sore thumb. Both are obviously embarrassing. But frankly, being overdressed is way better, for so many reasons.

You can always take off a layer of clothing when you’re overdressed. You can lose the necktie or your earrings to fit in a little better. You can’t do that when you’re underdressed. A suit jacket or a nice pair of heels isn’t just going to magically appear on your body.

Being overdressed is a lot easier to pull off because at least you look good while you’re doing it. The sting of embarrassment is easier to take when you look hot as hell. Being underdressed is far worse because not only is it embarrassing, but you also just look like a bum.

Another reason being overdressed is better is because you can always throw together some excuse to play it off. “Oh I just wanted to look my best tonight” or “I couldn’t go home to change after work.” When underdressed, there are no good excuses that sound believable — at least none that aren’t embarrassing in their own right. You could say your suit or dress is at the dry cleaners, but then you look forgetful too.

So while being underdressed or overdressed are both embarrassing, being overdressed is way better. While being underdressed may be a good test of your personal confidence (which everyone needs once in awhile), sometimes you don’t want to test your confidence. Sometimes you just want to fit in. It’s easier to do that when you’re overdressed. You can lose layers or throw together some excuse and, you know what, at least you look good.

— Matt Gwozd

Counterpoint: Underdress and Own It

Underdressed all the way. We’re in 2017, a world of athleisure and minimalism, where with a confident toss of your hair you can stare down a pompous overdresser and announce, whether truthfully or not, that your leggings are couture. You’re not underdressed, you’re just trendsetting.

You’re also going to be comfortable. Underdressing wins the comfort contest, hands down. Do you really want to be tottering on stilettos when you could be wearing your comfy old sneakers? The more comfortable you are, the more at ease you’ll be. It’s easier to think of witty comments at a cocktail party when your feet aren’t killing you and your hair isn’t pinned up into a heavy, headache-inducing arrangement.

Everyone knows that when walking into a room full of ballgowns, being underdressed is embarrassing. It’s not because you’re wearing sweatpants, though. It’s because you’re wearing something different from everyone else. It would be just as embarrassing to walk, decked out in a ballgown, into a room full of people wearing sweats. If you find yourself underdressed, own it. There is an effortless confidence that goes with underdressing.  It dares the room to call you out on it.

At the end of the day, there aren’t many places you can show up to underdressed anymore. People wear jeans and leggings to the theatre, church, the symphony, and out to dinner. Wherever you are, there are other underdressers that have gone before you. Know that you are in good company with other people who were in a hurry, were tired, forgot what day it was, or chose comfort over style. Walking into a room full of ballgowns in sweatpants could be embarrassing, yes, but only if you let it be.

— Shay Lewis

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