[Free] You Look Better When You Try Hard

And frankly, most people aren't in danger of trying too hard.

This article used to be paid, but in lieu of Many Such Takes (taking a break…for now, anyway) I will be re-publishing some of my paid content as free every weekend.

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I recently finished reading The Viral Article that distinguishes “fashion insider” aesthetics from “influencer” aesthetics, opening with the defense of Chloe Malle (Anna Wintour’s “sort-of-successor”) and the way she presents herself. Notably, according to her critics, she is not super “done,” and nothing she’s wearing looks terribly cutting edge or trendy. But alas, she is High Fashion, something that confused the Internet commoners.

The aforementioned article then explains how much of what we think is stylish is actually low-brow Kardashian slop, from fillers to fake nails to My Little Pony lashes. While I generally liked the writing, this did feel a bit warmed over. It was “What Old Money Actually Looks Like” Instagram Reels redux, if you will. Not to do the ultimate meta reference of Anna Wintour but, “Elegance by not trying at all? Groundbreaking.”

The author isn’t wrong, per se. She’s right that over-the-top high maintenance looks read as less elevated, less elegant, and less chic. It actually feels very obvious to the point that I’m surprised anyone needed an explainer. But there were a few moments where she described a certain horseshoe effect of beauty where the nonchalant, effortlessly chic aesthetic is indistinguishable from the way someone who actually doesn’t give a shit about fashion at all might look. For example, she says that true fashion insiders don’t wear nail polish or even mascara. This led to a bunch of people who don’t put any effort into their appearance, and have no interest in looking like a fashion insider, patting themselves on the backs for being ultra-chic by mistake. It’s giving:

The only problem is, most of you—most people in general—are this guy:

It’s fine if you want to be that guy, by the way. I feel like it’s worth mentioning that despite all the content you might see online from glamorous women and ultra-fit men, most people don’t put any effort into their appearance or clothing beyond “wouldn’t get kicked off a Spirit Airlines flight.” Even in big cities like New York or Los Angeles, most people look completely unremarkable, and you can tell fashion is the last thing on their minds. And that’s fine! While I enjoy people-watching for the fashion and styling, I acknowledge that nobody owes me a LEWK.

But because so few people care about fashion at all, it’s very hard to accidentally look like a fashion insider because you don’t care about how you look. If you’re putting in very little effort into your appearance, will people be more likely to mistake you for the 0.1% of people who are fashion insiders, or the 70% of people who are just going to Costco to pick up toilet bowl cleaner? Ergo, I would not give anyone the advice to stop wearing nail polish or mascara to appear more elevated. I acknowledge that’s not really what the author of the aforementioned piece was trying to do, but it’s probably how a lot of people took it. If they aren’t already a fashion insider and showing it in other subtle ways, the bare nails and bare lashes will not read “too busy jetting off to Paree to possibly have the time.” They will just read as “nothing” as Phoebe Maltz Bovy also put it.

I’m going to make a wild generalization here, but most people are not maximizing their appearance. Some of those people don’t want to maximize their appearance (and to them I say, good day! Keep doing what you’re doing!) but there are other people who probably would like to look more attractive (and especially if they’re women, more fashionable and chic) but because of time restraints, money and energy, they just don’t. These people are generally not in danger of trying too hard. It’s very time-consuming to put as much effort into your appearance as Kim Kardashian, and most people wouldn’t be able to do that even if they tried. Excluding people who truly don’t care about how they look, most people are putting in less effort than would be optimal.

I would include myself in this, by the way! Previously, I wrote about my lack of MILF-maxxing and the fact that I’d probably look better if I devoted more time to things like professional haircuts, doing my makeup every day, and maybe even getting some subtle cosmetic enhancements. Ultimately, I decided to split the difference and just start retinol because it’s not that important for me to maximize my appearance. But I acknowledge I am not currently doing as much as I theoretically could be doing to look my best.

One problem with the quest to appear like a fashion insider is that, like the whole Old Money thing, this teeny-tiny segment of ultra-chic people don’t appear that way because they’re not wearing makeup (or in the case of Old Money, because they’re wearing some old fisherman sweater full of moth holes, as people supposedly “in the know” keep insisting they are) but because they are…what they are. It’s a very “if you know, you know” kind of thing which means that only a small percentage of people could even pick up on you belonging to the secret club. Attempting to emulate it will not work if you are not already part of it. And attempting to emulate this level of fashion elevation by putting less effort into your appearance is just going to make most people just look a bit more schlubby, not like a Vogue editor.

It reminds me a lot of a common thread I used to see on Reddit’s r/femalefashionadvice. Every few days, a woman would post a photo of Cara Delevingne in a ratty sweatshirt and messy top knot and say, “Why can’t I look like this when I do the off-duty-model look?” Someone would always state the obvious which was that she couldn’t look like Cara Delevingne in a ratty sweatshirt because she wasn’t Cara Delevingne, and then she’d be downvoted for being fatphobic and ageist and OP would be reassured that if she only found the right drape of a ratty sweatshirt she could pull it off. But the reality is, the words “off-duty” are doing a lot of heavy lifting in the term “off-duty model.” I feel like “model” is a pretty important qualifier here. If you are not a model, and do not look like a model, you will not look like an off-duty model because you wear a hoodie. When I drop my kid off at school in my lounge clothes, nobody is wondering, “Who’s that model?” unless they’re referring to a spokesmodel for the latest anti-anxiety medication on Hers.

First of all, some of these looks are obviously ON DUTY.

It all reminds me a bit of the discussion about men who are “too muscular.” A while ago, when a man’s pre and post-fitness bodies were juxtaposed and women were asked to say which they found more attractive, I speculated that even if most women found the higher body fat, pre-fitness image more attractive (which was still pretty fit) it doesn’t mean that men should take the advice that fitness will only repel women and that they should stop trying too hard. I said this mostly because it’s very rare to meet a man who is “too fit” to appeal to women. They absolutely exist, but they are competitive bodybuilders, and most women will not encounter a man like this in the wild. Most single men don’t have to worry about accidentally becoming too muscular for women. Especially if a man finds fit or thin women attractive, I have concerns about them seeing “Jack Black is actually my dream man!” posts and thinking they’d be best off looking like Jack Black. No offense to Jack Black, of course, but one of the reasons Jack Black is so popular is because he’s Jack Black, not because he’s not fit. All other things being equal, guys who are in good shape generally do better with women than guys who don’t work out.

I should clarify though—this influencer vs. insider stuff isn’t about attracting men. Arguably, attracting men is a different ballgame entirely and nails would fall into the category of “past the point of diminishing hotness,” which I wrote about before. The fashion insider stuff is clearly about status signaling to other women, which is as fine a goal as any, by the way. But it reads a little like the woman-to-woman version of guys who say “We don’t like makeup and fake boobs, we want an all-natural girl next door!” and then post a literal supermodel wearing natural-looking makeup.

This one was posted by a woman, which is even weirder.

Given that only a small percentage of a small percentage of the population would be able to identify that you were a fashion insider, and not just some lady who doesn’t wear nail polish, attempting to look like one feels particularly futile.

Of course, I want to underscore that the author of the original Viral Article is not wrong. There is a particular “too-done” look which immediately outs someone as not elegant, despite the fact that they’re clearly doing their darndest to look elegant. On a recent European vacation, I kept spotting these women who looked so perfect that you could tell almost everything they did was for an Instagram photo, and the perfection cheapened their overall look even though it was clear they had spent lots of money and time on it. Think absolutely flawless makeup—heavy but clearly intended to look natural with perfect subtle contouring, large Chanel logo earrings, stiletto heels, cocktail dress at 10 in the morning, possibly fake boobs, the whole shebang. Take this $760 Nana Jacqueline dress, for example:

I actually kind of like it, to be honest. It’s kind of cool. But it would look really bizarre in any location but a formal party (or influencer’s photo op at a French tourist trap cafe, which is basically my point.) But outside of a formal event, it actually reads less elegant than something like this from DOEN, which is less than half the price. The model’s casual makeup and hair are also relevant:

I’ve made this “mistake” for years, but in my defense, I wasn’t trying to look elegant, I was merely trying to serve cunt.

Anyway, assuming you aren’t already famous for being a fashion writer or model, you won’t look very elegant in the over-the-top pink satin cocktail dress, but you also will not look elegant at all in this:

So here’s my advice, even though nobody asked. Assuming you aren’t actually a supermodel or fashion insider, the way to look your absolute best is probably in the space between Kardashian-tier influencer and fashion insider stereotype. You know, like the black DOEN dress above. Obviously, this isn’t realistic for everyone (myself included) but wearing high-quality clothes that are on the upper end of dressy for what you’re doing (but not outrageously overdressed) is probably a good start, along with getting regular mani/pedis that aren’t particularly flashy, doing your makeup in a way that’s flattering and classic, and having a good haircut and color.

Boring, I know. I’m aware that this is not what a fashion insider would do. But if you aren’t a fashion insider, nobody will ever mistake you for one.

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