The other day, I received a question via Instagram: “I’m constantly worried about overdressing. Would MR write a story about the psychology behind this?” Under the suspicion that my colleagues might have more thoughts on this matter than anyone in her right mind should, I posed it to them. Literal paragraphs followed, which I found both endearing and validating. I’ve input all of them below, along with my own thoughts, as I found the breadth of answers interesting enough to run as a story in its own right. Whose do you connect with more? What’s your overdressing hangup, or do you have none at all?
A desire to be slightly underdressed feels like a tenet of my personal style. If I had a Pinterest board for outfit inspiration, it would be all slouchy pants and roomy T-shirts, worn in just the right proportions and combinations. I’m involuntarily drawn to anything that either looks or feels casual, even if it’s technically not. Leandra recently mentioned that her favorite occasion to get dressed for is that in-between morning activity: grabbing coffee, running to the store, getting a bagel. I connected with the sentiment immediately, although I’m sure for different reasons. For me, those kinds of New York errands require peak chill-wear — an opportunity to maximize comfort while still maintaining personal style. I think my affection for that intersection is part of why I connect more with Brooklyn than Manhattan: there’s an ease to the style language here that permeates how people behave.
I felt off when I recently wore this around Bed-Stuy, for instance. Even though my shoes were flat and my shorts have an elastic waist, something about how it came together felt too dolled up for my taste. That is part of why I enjoyed it, I suppose, but by the end of the day I was eager to take it off and return to myself.
Even if I’m dressing up, I usually try to do at least one styling trick to feel a little dressed down: messy hair, an oversize dress, flat shoes, no makeup. Something has to throw off the balance or I feel uncomfortable. When I ask myself why that is, though, the obvious answer is I don’t want anyone to catch on to the extent of how much I try — because then the jig would be up. Then everyone would know that none of this comes all that easily to me. That, underneath it all, I’m actually quite plain and uninteresting. I’ve never put words to that particular sentiment, though, and it sounds really sad! I wonder if it’s true. In reality, I don’t actually think I’m plain and uninteresting, I just think society expects a lot of me (and all of us) aesthetically, and dressing down lets me reshape that narrative.
I fully realize that my feelings about the concept of “overdressing” are a product of the fact that a) I live in Manhattan, where you can wear anything from a shoebox to a sequined unitard without batting a stranger’s eyelash and b) I work in the fashion industry, where expressing your creative self through clothing in all forms is not only encouraged but professionally valuable. Truthfully, though, I have no feelings about overdressing at all. I never think about it! I wear exactly what I want to wear, whenever and wherever I want to wear it. Sometimes that means wearing jeans and a T-shirt to a dinner where I know all my friends will be dressed to the nines, and sometimes that means wearing a party dress to the park. Reservations around what you’re “supposed” to wear seem almost antiquated to me, like the anecdote my grandmother tells about how she was only allowed to wear skirts and dresses inside her sorority house in college. If you’re worried about overdressing, I think it’s a symptom of something deeper. It’s a sign that you’re letting forces outside yourself (i.e. concern about what other people might think) dictate how you dress. The antidote? Your very own guts.
We’re like the long-winded paragraph committee, this is mine:
Philosophically, I love the concept of overdressing — that if we are considering the monotony of a regular day, what you wear is in opposition to what you do. To see a stranger delighting in the fancies of a sequined top, structured skirt, feather pants or rhinestone shoes while walking with two grocery bags in tow brings genuine satisfaction to me; it is within this contrast that I feel most comfortable. And speaking of getting groceries, some of my favorite events to dress for are defined by their briefness: picking up dry-cleaning, a deli run, stepping out for a morning coffee. Theoretically, these events occur as extensions of being home and thus demand nothing more or less than un-ironic sweatpants, which is where I see an opportunity to soup myself up. Get overdressed to engage in quotidian errands. This doesn’t necessarily mean a chiffon gown (though it could!), so much as it does an evening bag with a nightgown, or conflicting, strappy footwear with a silk shorts set. You can call it buffet dressing, but for the purpose of this argument, I’d rather think of it as the dazzling difference between a shit day and a great one, made possible by nothing more or less than the clothes you’ve chosen to wear. Also, though, what you wear is so damn personal that it feels dated to suggest any form of it is “under” or “over.”
I’m a “depends on the situation” kind of over-dresser, but almost always, I prefer to be appropriately-dressed. I love specific dress codes and knowing what the overall dress-up/down theme of my friends’ outfits will be if we’re going somewhere. I like to check to see if everyone’s doing pants or skirts, heels or flats. If people tend to wear long dresses to some annual party, if it’s a swimsuit-and-flip-flops kinda place or more of a full-look kinda thing, I like to be informed about what to expect. NOT THAT I WANT TO MATCH WITH ANYONE. (I hate that.) I just like to know my audience, and I like to acclimate to the location around me. An exception to the rule was the one time I accidentally wore jeans to my friend’s 30 birthday where the invitation pretty explicitly said no jeans, but somehow I didn’t think about this while getting ready. Now it’s a running joke between us because, plot twist: I had a hand in writing the copy for her invitation. I was technically underdressed as a result, but because there was so much going on up top, I was fine with it.
I grew up in San Francisco, where 10 times out of 11, you’re better off underdressed — with layers handy. Maybe as a result of that, I’m always most at ease in jeans and least likely to wish I could go home and change if I’m wearing a sweater (weight dependent on season and weather). But in New York, because of the nature of 800 million things going on a night, you can get away with everything and anything, because who knows where you came from just an hour ago? Could have been a team-building indoor rock-climb or a black tie shindig.
No matter what, though, I can’t stand feeling sloppy, and I fear being even the littlest bit cold. Those are my two biggest concerns when getting dressed, almost always, more so than under/overdressing.
I am the kind of person who needs a reason to get dressed up, but when you give me one (like a wedding), I’ll go alllllll the way out. So what’s fun is when you are coming from somewhere fancy, or somewhere where you went full “fashion,” just totally to the nines, and then meet your friends in the opposite scenario, like at a dive-y local bar. I don’t know why I love that so much. Maybe it’s because you get to feel really special, or maybe it’s because no one seems to care at all and you remember that you can, in fact, wear whatever the hell you want.
Being overdressed is my greatest sartorial fear. In general, I try to strike a balance between looking nice but not calling any attention to myself by walking into a room in a full on OUTFIT when everyone else is in jeans. It always seems like a record-scratch moment of calling attention to oneself. I think about that costume party scene in Bridget Jones’s Diary every time I get dressed.
Although I always prefer to be underdressed, I keep a statement lipstick or fancy earrings in my purse in case I fall too far into the just-rolled-through category. I think it probably ties into the desire to be a cool girl who doesn’t try too much: someone who can just breeze through life confident in herself regardless of outfits, where the most fussy thing on her garment is a set of pockets, but I also am someone who literally stands out in a crowd because of my genetics and I spent a good part of my life just wishing I could blend in and am deeply resistant to wearing things that go against that.
How do you feel about overdressing? Do you fear it? Love it? Never think about it?