#197: What is "personal style"?
+ my thought on the Substack discourse & being "a failure"
Hey and welcome back to Dear Baby!
I’ll be answering three questions today: One about how to cultivate personal style from someone who regularly has mini-breakdowns while getting dressed, my thoughts on the “Substack discourse” (niche one for the newsletter heads), and lastly, how to manage feeling like a failure while hunting for a job that isn’t materializing. Warning, this round is long as hell. Thank you thank you for all your question submissions, I cherish reading them!
On cultivating personal style
“Dear Baby,
Wondering your thoughts on style, taste, and confidence. I just turned 28 and one thing I’m focusing on in transitioning from my post-college years into an ‘adult’ is cultivating my personal style and investing in quality pieces that I enjoy and will wear for years to come. I feel like I’m struggling with this. My dream is to have a closet where I can easily find an outfit for work, errands, going out, etc, that expresses my style, is flattering, and that I feel confident in. I find that more often than not, when I get ready to do any of those things, I fall into the trap of trying on everything in my closet while having a mini-breakdown that nothing fits any of those criteria. I go back and forth between thinking this is just an issue of cultivating my taste (i.e. a solid understanding of the true silhouettes, cuts, styles, and colors that suit me) or thinking this is just an issue of self-confidence that no amount of Instagram Reels on dressing for my body type and hours scrolling online shopping will fix. Is there an ‘end’ to cultivating your style? Does ‘the perfect wardrobe’ exist? How do I enjoy the journey?”
I definitely could have written this question at various points in my adult life! Part of the reason fashion is so complicated to love is its inextricable link with vanity—to put time and energy into it is to walk a tight-rope with your self-respect. Do you get dressed to honor, express, or delight in yourself, or to fit into someone else’s idea of worthiness? Do your clothes enable you to be present and engaged or do they push you further inward? Is your style connected to your values or does it feel like a commercial product, disconnected from how you otherwise operate? Is it additive or parasitic? Fashion can be just as inhibiting as it is liberating, and most of us experience both sides on and off. It’s hard to pin down.
I sense this ambivalence in your question. You’re either on the cusp of this sustainable source of well-being by way of finally buying the right stuff, or you’re lost, looking for confidence in all the wrong places. My first suggestion is to disabuse yourself of the notion that you’re going to solve this riddle by studying harder. I think you know that deep down. The Instagram Reels about how to dress for your body type and the endless online shopping are junk food for your anxious mind to chew on—they work because they feel immediately satisfying but are unsustaining in the long-run. You can chase those little highs forever, build a closet packed with technically flattering and stylish clothes and still be scrolling, looking for your next hit. Consumerism is an addiction! That kind of void doesn’t close by being filled. It has to heal.
The idea that we’ll gain confidence by buying the right stuff is one we’ve lifted from marketers whole-cloth. In my experience, it tends to happen the other way around. When I’m feeling confident, my taste is more reliable, grounded, and steady, and I’m able to shop slowly and with more patience. In the end, what I buy may contribute to my confidence, but only because it was already there, developed over time and, importantly, through other means.
Time is probably the most important factor. Like I mentioned in my critique of Emma Chamberlain’s house tour, “personal style” feels soulless without a little patina to it. Years may pass before you feel like you’re onto something, and this process will likely involve plugging your ears to the siren song of trends until you realize you actually have the same sensibility you had as a kid, it’s just grown up now. I like the word sensibility, I’ve started using it instead of taste when I’m trying to tap into something deeper. My sensibility is more personal, time-tested, idiosyncratic: the colors, textures, and moods I’ve always gravitated towards. It applies across contexts and is easier to trust than my tastes, which are more likely to shift with trends and culture. My sensibility is basically consistent, and dovetails easily with the rest of my life and personality, because I came about it organically versus by algorithm.
When I’m feeling overly eager (almost panicked) about some kind of shopping endeavor, like wanting a whole new wardrobe when a season changes or hoping to make over my entire apartment, this is always a sign to back off, because I’m going to buy things I won’t like or cherish in the long run. I’ve brought this quote up before in this same context, but it bears repeating: “Desire that arises in agitation is an expression of the ego; desire that arises in stillness is an expression of the soul.” That agitated feeling of hating all your clothes, wanting everything to change suddenly—this isn’t a shopping problem, it’s a spiral of insecurity that needs a different kind of tending. How can you slow down, take stock of what you have, what you like, what makes you feel good, and accept where you are for a while? There’s no harm in feeling unfinished. The harm is in assuming that’s a problem.
Some classic shopping advice you probably already know but may need to heed better: When it comes time to acquire something new, try to do it from a place of relative stillness, or at the very least, out of a careful curiosity. When possible, buy higher quality clothes less often, in natural materials. Cheap or polyester stuff can look great or even look expensive, but it often doesn’t wear well over time (or even in the short term if you look closer, the way it clings or attracts dust or feels on your body). Return stuff you don’t love or that doesn’t fit exactly right. If you tend to buy a lot of one type of item, e.g. you always buy pants, rarely tops or shoes, try in earnest to refocus; another pair of pants is not going to fix your lack of tops. If it helps, figure out a few words that describe your sensibility and use those as a litmus test when you want to buy something. Imagine having the item for years. This is a slow process that can be kind of boring. It’s not a movie makeover montage, which is sad for all of us, but in the long-run, it’s a much more reliable (and sustainable) way to build a wardrobe.
I’ve written about this before, but I think buying too much can inhibit the process of finding your style, or make your style worse. Leaping from high to high, you mistake the rush of novelty for confidence, spend less time with the stuff you own, and begin seeing the inevitable shopping comedown as proof that your closet still isn’t right, when you’re probably just bored because it isn’t new. Spending more time with your closet, forcing yourself to get creative with it, trying out combinations you wouldn’t initially think to try—these are all ways you can explore without constantly feeling like you’re starting over. I’ve only become a slow shopper in the last few years, and I think this is the single biggest contributor to my lack of mini-breakdowns while getting dressed (although this may jinx me).
One of the pitfalls of fashion is how it can encourage you to see yourself in the third person—an object held up for judgment. Try to keep in mind that your goal isn’t to look like a walking advertisement for a certain sort of person (a contest with no prize). It’s just to feel good in your clothes, embodied and present. “Finding your personal style” suggests you’re pursuing something specific, but I think it’s more abstract than that—more like self-possession. If you can gather the requisite patience, this is as much of an inward search as a practical one.
On the Substack discourse
“Hi Haley, I'd be curious to hear your POV on all this newsletter discourse. As someone new to publishing on Substack with no following, I constantly struggle with imposter syndrome. Obviously, anyone looking to write full-time on Substack is probably well-versed in the platform and reads widely but I worry that I've internalized so much of other people's style that I won't be original enough or my content won't be good enough or worth reading. If you were getting started now and hadn't had a following from MR, what advice would you give to someone who cannot get a media job but has some experience in adjacent fields and some academic training as a writer?
Emily Sundberg’s “The Machine in the Garden”
Alex Brown’s “Who’s Even a Writer Anyway?”
One Thing’s “What Makes a Good Newsletter?”