Style Advice Is Killing Your Style

How do I dress like a cool girl? What shoes are they wearing in Paris? What color combinations look old money? Are crossbody bags still okay? What should I wear with white jeans? How do you layer necklaces? Are polka dots in for summer? Are jorts feminist? Is butter yellow my friend?

Style advice catered to the masses is nothing new: this article about the color red from 1953 is spiritually identical to this one about deep purple from last week. And this one about aquamarine, also from last week. And also this one about green apple from this week. All of these articles are on the same website and, are, of course, filled to the brim with affiliate links to items in each color.

I imagine the kind of person who genuinely seeks guidance through articles like this: she’s sick of defaulting to all black, or she bought into the drab neutrals of the “quiet luxury” trend or she went all in on butter yellow for spring but realized it made her look a little jaundiced. Now she’s looking to inject her wardrobe with some new color but doesn’t know really know where to start. Where does this leave her?

It used to be easier. Not easy, but easier: you’d get up and go to a store, you’d see what’s being sold (and what other people are wearing), you’d look around, you’d feel things and try things on that seem promising. But, mass produced/fast fashion sucks, department stores are dying, and those cool, indie boutiques aren’t all that accessible.

So, you retreat online, and immediately get overwhelmed. There’s thousands of brands, with hundreds of styles, and plenty of perfectly curated social media pages showing off every possible trend that you need to buy right this second. But you just want jeans. But which jeans? Which jeans do you wear if you’re petite? What if you’re petite with a big butt? What if you’re petite with a big butt and brown hair? What if you’re petite with a big butt and brown hair and two cats named after Greek goddesses and you listen to Bauhaus but you wouldn’t call yourself goth but you do wanna look a little alternative to fit in at your favorite local coffee shop where all the baristas have perfect hair?

Now, you’re spiraling. The advice you seek gets more and more granular, yet no more helpful. After days of scrolling, adding to and deleting from various carts, and asking strangers on Threads, you settle on a pair of slim, cropped jeans (seen on Bella Hadid but they’ll totally work for you even though you’re not Bella Hadid) and they arrive and you wear them for a season but you don’t really love them and now you’re seeing everyone in barrel jeans. Should you get barrel jeans? Let’s ask the internet again.

It’s a trap! You’ve been thrown into a cycle of outsourcing your thoughts and desires, purchasing things prescribed to you, never really feeling satisfied with your choices, and doing it all over again every few months. The problem, though, is not that you need guidance. We all do, sometimes. The problem is you don’t trust yourself enough.

Style and confidence don’t just happen, they’re skills that require not just active practice but active decisions. And with so many of us living our lives online, where any question we have can be answered in a matter of seconds by someone other than ourselves, who’s more than happy to get a cut from whatever decision we make, we’re allowing those skills to atrophy. We seek out easy answers, we hunt for that one bag or pair of shoes that’s gonna fix everything, and we start to take everything from clickbait articles to sponsored posts to the random tweets of strangers as a directive. And at no point do we stop and ask ourselves “well, what do I actually want?” No soul searching, no experimentation, no pros and cons lists, just phone (or computer).

I can’t help but feel that this desire to find a shortcut to style and expression is tied to a whole host of larger societal issues: the same need for instant gratification that leads to rampant exploitation of labor and resources; capitalism’s constant push for “optimization” and productivity at all costs resulting in burnout and chronic illnesses induced by stress; the rise in anti-social behavior leading to alienation and loneliness…it is that deep!

How do you escape the trap, stop depending on being told what to want, and cultivate a style that’s all your own? How do you gain confidence in your ability to make choices and maybe get it wrong sometimes but learn from it and allow yourself to grow? There’s no quick answer, just like there’s no quick answer to whether you definitely need a pair of Mary Janes. What you have to do is develop your taste. And no, I don’t mean “taste” in the way that every Substack essay talks about it—as an innate knowledge and love of whatever makes you look like the most interesting person in your friends’ Instagram feeds—but taste as in, you know, what you like.

This article isn’t about that, though. This article is about recognizing the problem, starting with:

Making up problems you don’t need to solve.

In researching this post, I came across an article on Refinery29 titled “11 Summer Pedicure Colors That Go With Pretty Much Everything.” It was mostly just pictures of feet (for free!?) pulled from random Instagram accounts, but all I could think was—wait, is my pedicure supposed to go with everything? Is it wrong if it doesn’t?

So many of these advice articles carry a not-so-subtle implication that you should be doing something, and if you’re not, you need to fix that immediately. They manufacture a problem, and then swoop in with a monetized solution. Teen Vogue says we need a sunscreen combo we’ll reapply as much as our lip combo—but what if I don’t have a lip combo? Do I need a lip combo? Elle says everyone suddenly wants a great watch, again—don’t you? This kind of framing—presenting things as an understood no-brainer that you’re already late to—is prevalent in a lot of industries (haven’t you noticed how suddenly you’re not getting enough protein?), so, of course it’s a major part of the Style Advice Industrial Complex.

The point is to make you anxious and unsure of yourself. To make you feel like you’re perpetually out of the loop while everyone else is doing so much better at this style thing. Here’s the thing, though: you’re fine. Maybe one day, your toenails didn’t perfectly match your dress. Guess what? The world didn’t end. The internet said wearing denim jackets makes you look over 30. Guess what? You are over 30. If no one’s ever commented on it or made you feel lesser than for wearing something in your actual real life that matters, guess what? Even then, if you’ve never looked in the mirror and thought “I hate this,” before reading that you should, guess what? It’s not a problem. You don’t need to make it one, and you definitely don’t need to search endlessly for solutions. Close the tab.

Knowing the language but not yourself.

You see every trend, every new silhouette, every print that’s suddenly everywhere (sardines?), every street style report from every European city, and every runway pic but you still can’t decide what white t-shirt is right for your wardrobe. You still have no idea how to describe your style. “Wrong shoe theory,” and “office siren,” and “whimsy” are embedded in your very brain matter but ask yourself what silhouettes make you feel good, or what colors you reach for instinctively, and you draw a blank. The internet gives us so much language for aesthetics and “hacks” while actively discouraging us from developing one of our own.

One thing I notice is how many of these videos breaking down trends and tips and tricks for style use real people—or, rather, real people on the internet. I propose we get a little realer. I am a big proponent of searching for inspiration and moodboarding online, but, when you’ve gotten a little too online, and a little too attached to labeling everything, it might be time to go outside.

Since I’ve relocated to Tirana, Albania—no doubt inspired by the very European habit of staring freely at people—my favorite thing to do is observe the people around me. I make it a point to put away my phone and look at my surroundings, obviously focusing on what everyone is wearing. And it’s what I think we should all be doing. Rather than looking to perfectly curated online images meant to get us to click or watch and subscribe or buy, or trying to find the next styling hack that’ll change our closets, look at what actual people are wearing. Even the least stylish place (like Seattle) has something to offer.

Fear of making mistakes.

I’m going to be a little harsh, but, I promise, I say this out of love: you don’t need to ask if burgundy and yellow or green and blue or pink and orange “look good” together. If you have a top in one color and a skirt or pants in the other, you can just…put them on and see for yourself.

When you rely too much on outside guidance and instruction, though, you quickly get in the habit of waiting for confirmation before doing anything, and end up doing nothing at all.

The answer is my favorite thing to do: play dress up! If you see something you like and are wondering how you can make it work, or you come up with a silly outfit idea, or even buy something new that you’re not sure about, don’t wait around until the day you have plans to try to figure it out, figure it out now, or, you know, at your soonest convenience. Even if it doesn’t work right then, study it while it’s on and figure out why. Compare it to your inspiration, try to pinpoint what’s different and what you can change (and then change it and try that, too). If you think it looks good—and, more importantly, it feels good—test it out on a random outing. Again, don’t wait until you have super important plans: wear it to run errands, to grab your DoorDash/Deliveroo order, to dance around your room to the new Carly Rae Jepsen song, whatever.

Treating every new outfit or garment like an incredibly high-stakes mission you can’t mess up is a hard mindset to get out of. It’s what leads to us putting our best clothes in the back of the closet, defaulting to leggings and hoodies, and sticking to “safe” purchases that neither make us happy nor say anything about us, and it’s something you just have to work through by wearing the clothes. Above all, though, I find this fear leads to what is, perhaps, the biggest problem with constantly seeking out Style Advice online, and that’s:

Seeking objectivity in the subjective.

Does navy go with black? Should you wear maxi skirts if you’re short? How do you layer necklaces? It depends!

Yes, sometimes navy and black are too close in value and make you look like you got dressed in the dark if you pair them, but sometimes it looks really cool and daring. Yes, sometimes a maxi skirt might cut you off at the wrong part of your leg and make you look like a shrunken version of yourself, but it can also hit exactly right and make you look like tall and statuesque. Yes, you can pick necklaces that are the perfect lengths, or you can just throw some on and embrace a messy, tangled look. Style has no universal answers, but so many of us spend time looking for someone to hand us one anyway.

It’s because when you ask “should I wear loafers,” you’re not really asking about loafers, you’re asking for permission. And, I’m sorry, but you’re not going to get it. Not because you don’t deserve it, but because no one can give it to you except you.

Contrary to what it may seem like, I’m not telling you to stop seeking advice. I’m not putting myself out of a job, here. I want you to learn from others. But you have to stop feeling like you’re being graded, or like there’s some version of “correct” you just haven’t achieved yet. Instead of looking for advice before you try something new, how about you just do it? And if it doesn’t work the first time, then you can decide if it’s worth learning how to make it work, or, if it’s just not for you.