This has happened to me again recently. Last Tuesday I was standing in line at Blue Bottle Coffee (Okay, I know, I know, I shouldn’t admit to shopping at such a place, but honestly, their coffee is decent). I was wearing jeans (Straight leg, dark wash. Everlane. Okay, fine, these are the most basic, unremarkable jeans I’ve ever purchased. I also wore a white button-down I’d owned for probably three years. My black loafers. A navy blue blazer (a.k.a. “the emergency blazer” — basically the only thing I own that’s remotely stylish). Honestly, it was a fairly unremarkable outfit. An outfit I would normally choose if I was running late but still needed to present myself in a somewhat professional manner.
Someone behind me in line starts talking. You know how this works. For a short period of time, everyone becomes friendly due to the communal experience of waiting for coffee. So this person is chatting with me and says, “You always look so pulled together! You must spend forever picking out your outfits.”
I literally almost burst out laughing. I was wearing clean jeans. That was the extent of my sartorial decisions. The shirt was wrinkled from being shoved into my work bag the previous day because our office air conditioning was broken and I had overheated. The blazer had coffee stains on the sleeve and I was using my purse strap to hide them.
Anyway, that’s the thing — and this is why I’ve been pondering this since then — there is this strange notion that appearing well-groomed appears to happen by accident. As if you simply rolled out of bed with perfectly tousled hair and happened upon the exact combination of clothing that creates a chic, thoughtful image. This is an unrealistic ideal, as you’re expected to care enough to look good but not enough to notice when others realise you made an effort.
Honestly, it’s exhausting.
Over the years, I’ve watched people wrestle with this issue. Through writing about fashion and through simply observing the world and paying attention to the clothing that people wear, I’ve seen that the most complimented outfits are always the ones that look effortless. No one will rave about the person who has clearly spent hours preparing themselves. We save our most enthusiastic praise for people who look like they achieved perfection by accident.
Sarah is a lawyer who has to dress professionally for court but manages to look like she just threw on whatever was nearest her bed. Until she had a few too many drinks, she revealed to me that she spends hours each evening preparing her wardrobe for the next day. She steams her clothes and has backup options in the event that something doesn’t work. “The secret,” she explained, “is strategic messiness. I always ensure that one aspect of my outfit looks a bit rumpled.”
For example, she will wear a perfectly tailored suit but intentionally muss her hair. Or, she will wear a sleek ponytail but make sure to create a small wrinkle in her shirt. Never enough to make her look sloppy, just enough to make her look human. Relatable. As though she didn’t try too hard.
As I began to pay closer attention to my own closet after that conversation, I noticed that the outfits that garnered the most compliments weren’t my most carefully constructed outfits. Rather, they were combinations that seemed obvious in retrospect but somehow felt new and thoughtful. Usually it’s a mix of something upscale and something completely ordinary — i.e., wearing my grandmother’s vintage earrings with a $5.00 T-Shirt from Target; or wearing a silk blouse with jeans that are literally coming apart at the seams but fit perfectly.
The key is making sure the upscale piece doesn’t overpower everything else, while the everyday piece doesn’t look like you gave up. It’s finding this middle ground where everything feels intentional but not overly calculated. Which is absurd when you consider it, because creating this equilibrium requires a tremendous amount of calculation.
I have this camel-colored coat that I saved up for months to purchase. It’s likely the most expensive single item I own, and it makes everything else I’m wearing appear more refined and professional. However, if I pair it with other obviously high-end items, I come off as attempting to prove a point. Therefore, I wear it with battered sneakers and jeans with tears in the knees. Or, I wear it over a $5.00 t-shirt from H&M. The inexpensive items elevate the quality of the coat, and the coat makes the inexpensive items appear less tacky.
My mother has this habit where she dismisses anything nice that she’s wearing. If someone compliments her dress, she’ll respond with, “Oh, this old thing? I think I got it at Kohl’s years ago.” Although I literally watched her order the dress online last week and spend twenty minutes researching reviews to ensure the best possible fit. It’s as though she is physically unable to simply say “thank you” and move on.
I used to do the same thing. Anytime I received a compliment regarding my appearance, I would immediately deflect it with a story about how the outfit was entirely unplanned; or that the item was extremely old; or that it was very inexpensive; or that I found it in the back of my closet. As if having pride in how you look is something to be embarrassed about.
However, what I’ve realised — and this may be a topic of contention — is that the individuals who actually look as though they have no effort in their presentation are simply aware of their own personal style so completely that they don’t require a lot of mental energy to decide what to wear. They understand what fits their bodies, what colours make them look alive, and what silhouettes flatter them. They’ve invested the necessary time and effort.
One example is my coworker, who always appears to be perfectly dressed. Always. Her outfits are simple yet flawless — nothing gaudy, nothing showy, but consistently well-dressed in a way that appears completely natural. I used to believe that she was simply born with the gift of good taste, until I realised that she basically dresses the same way every day. She has approximately five different blouses, two different pairs of pants, and three different cardigans, all in slightly varying shades of colour. She has essentially developed her own uniform, and adheres to it.
While this is certainly not effortless in the sense that she doesn’t think about it — that is effortless, because she has already completed all of the thinking. She has eradicated the possibility of decision fatigue by understanding exactly what works for her lifestyle, her body, her profession, and her budget. All of the effort occurred prior to each morning.
I am attempting to achieve the same level of clarity in my own closet. I have been gradually eliminating the items in my closet that do not actually fit, or that I do not truly enjoy wearing. Items that I continue to hold onto despite the fact that I never intend to wear them. Trendy items that appeared fashionable in the store but feel ill-suited to my actual body in my actual life. What remains is a more cohesive collection of items that ultimately represent me better.
My current uniform consists of jeans (dark-washed, straight-legged, from either Everlane or Levi’s); some type of simple top (a t-shirt, button-down, sweater, etc.); and either my sneakers or loafers depending on the activity I plan on participating in that day. I add a blazer if I need to appear more formally attired. Alternatively, I add a denim jacket if I do not. I have a limited selection of accessories that I actually enjoy wearing and use regularly instead of a large storage bin filled with unused items.
When I describe this as such, it sounds quite dull. However, it has been somewhat liberating. Instead of spending each morning deciding on a completely new outfit, I’m generally choosing among variations of a theme. And for some reason, those variations feel more like me than the experimental outfits I previously attempted to construct.
What’s bizarre is, since I streamlined my approach, I receive more compliments on my style. Not because the individual items are more elaborate or visually stimulating. Rather, because everything works together. There is a coherence to how I dress now that reads as intentional, even if I’m literally just selecting the first clean item I find.
Perhaps that’s the ultimate secret to looking polished without it being apparent that you’re trying — to develop a clear sense of your own style to the point where you could get dressed in the dark and still look like yourself. When your clothing accurately reflects who you are as opposed to who you believe you should be, or who you wish to impress, it appears more natural. More effortless, although the process of arriving at this realization likely took years.
However, I do have mornings where I try on four different shirts before settling on the first, and I do occasionally cheque myself out in store windows to confirm that my outfit is arranged correctly. The only difference is that I no longer feel ashamed of having pride in my appearance. If someone asks me where I obtained a particular item, or expresses admiration for how I’m dressed, I simply say thank you as opposed to immediately dismissing the compliment.
To be honest, looking good is difficult. Understanding what works for your body, your lifestyle, and your personality requires time, attention, and in some cases, money. There is no shame in desiring to present yourself well to the world. The stigma surrounding “trying too hard” is merely a means of making women (and women primarily) feel guilty for taking up space and wishing to appear attractive.
Perhaps the true skill is not the ability to look polished without trying. Perhaps it is taking the time to determine what works for you and then wearing it with conviction rather than apology. Perhaps it is acknowledging that a certain level of effort is required to create a wardrobe that represents your identity, and that this effort is a demonstration of self-respect rather than vanity.
To be frank, I am still working towards this goal myself. Old habits take time to break, and I still catch myself deflecting compliments. However, I am attempting to recall that when someone comments that I look nice, the correct response is “thank you” rather than “oh, this old thing.” Even if it is literally an old thing that I’ve had for three years and nearly donated to Goodwill on multiple occasions.
The idea of looking effortlessly polished is not about the lack of effort or the presence of effort. It is about authenticity. When you are wearing items that reflect who you are, it is difficult to replicate. And when you are comfortable in your clothing — whether that is because they fit well; because you selected them thoughtfully; because they align with your lifestyle — you carry yourself differently. With greater confidence. As though you belong in what you are wearing.
In a nutshell, that is the real trick. Not pretending that you don’t care, but caring enough to identify what works for you and embracing it. Letting your personal style serve as an expression of who you are, rather than a costume you are wearing. Which, when I state it that way, is perhaps a more effortless concept.
