Personal Style Is Overrated
When the quest to find yourself stops you from having fun
People are obsessed with personal style, but is that self-centered quest really the way to fit nirvana? Let’s talk about it.
There are lots of phrases we like to use that are redundant. Take for instance, “RSVP, please.” Which actually means, “respond to me please…please.” Or how about that favorite internet slop-phrase, “performative male?” Redundant, because inherently - any performance of manhood (or anything really) whether it’s matcha or monster trucks is… a performance.
I’ve begun to feel that way about “personal style.” The slop-posters have made a whole business of convincing you that by taking their rules you can optimize dressing like yourself. How’s that supposed to work exactly?
These hucksters want to convince you that you can build yourself into an impregnable fashion fortress - wherein only your good ideas and influences reside (except for their pointers, of course). Through heroic acts of self-abnegation, you can somehow learn to style all the same old shit that everyone has but in a way that is more genius - and of course, personal.
The serious business of developing personal style requires rejecting the fripperies of current trend. Can this hunt to be the most optimized version of yourself wring every ounce of fun out of dressing up? I think so.
What about fun?
You definitely start to feel the burn when clothing and style is your business. If your vision of how to dress resonates, people not only start to emulate you, but they react badly when they perceive you branching out. I.E. betraying the sanctity of your “personal style.”
The first time I recommended bootcut jeans in 2021, I was bullied so relentlessly, I took down the video. The people weren’t ready. (Look at us now.) Posting a photo of my vintage Armani suit with (gasp) fisherman sandals two weeks ago resulted in dozens of death-threats from the Twitter crowd. Sometimes these people are trolls, but other times they are members of the cult of personal style - the religion where experimentation goes to die.
What about dress-up?
If we zoom out of the myopic discussion around personal style, we mainly get dressed for specific contexts. I wear something different to have dinner with my mom than I do to meet my friends at a bar. Partially out of obligation to look one kind of nice for my mom and another for the homies, but the bigger reason is because it’s fun to dress up.
It’s fun to dig through my closet for a button-up that’s a bit dressier for the nice dinner - just in the way it’s fun to grab a threadbare tee for the night on the town. To call these thinks personal is redundant - you picked them out, you liked them, you bought them. What makes it fun is the small ways you dabble in trend and occasionally betray your own hard-and-fast rules.
Think of Ralph Lauren - whom many consider the personal style GOAT. But when I sift through his millions of fit pics, I really think the only consistent factor is… that he is Ralph Lauren. Here is a man who loved dress-up. One moment a cowboy, the next a blue-blooded New Englander: constantly breaking rules and mixing up archetypes. The joy of getting a little freaky with the fit.
Rules Are Made To Be Broken
The world’s worst dressers hate from the sidelines and their favorite refrain is “that’s against the rules!” Much in the way Ralph Lauren delighted in mashing together archetypes, innovative dressers combine things in ways that either inwardly or outwardly break rules.
There are the widely accepted rules like no black and brown together or white after Labor Day; but more importantly there are the rules you set for yourself early in your style journey that you continue to revisit as you learn more, shop more, and grow.
I closely associate the personal style shills with the daily uniform people and I feel that both groups (intentionally or not) discourage growth and experimentation. You can’t decide your style in a spreadsheet or with a stylist or from the comment section. You have to get out there and slowly but surely, push the envelope.
I could wear a white tee and sexy, fitted Wranglers every day and no one would bat an eye, but that would make me a spineless dresser. How have I betrayed some of my old rules this year? And how has it made me feel?
No Sandals Ever
I’ve never liked sandals. I can be a bit of a masochist and the comfort argument has never held much water for me. I cannot abide by the current fashion flip-flop movement, but when you’re in Italy in the summer, you are fighting for your life.
The fisherman sandal from Vinny’s piqued my curiosity. Clean lines, a nice buckle, and a dressy outsole definitely triggered something in my little brain. With absolutely no break-in required and record-breaking temperatures, I didn’t even wear my loafers once - even though they might technically have been the appropriate companion to my trousers. Certainly not for every context, but a fun way for me to branch out and avoid sweaty feet.
5 inch inseam
A few years ago, the 5 inch inseam was a bold move. A rebellion against a lifetime of dowdy summer attire. But now, it feels like a somewhat oppressive rule of law. Yes, there are people who strayed much too far in the opposite direction. (Capris and cargo shorts still make me feel ill.) But is there a middle ground?
My shorts with Uomo Copenhagen were a great test-case. We made them long (possibly too long), but with their pleats and volume - 5 inches was too short. After some deliberation, I found that all of them draped just right at 7 inches. I had them all hemmed and they rocked. A western belt, a tank, and a drapey vintage shirt - this is all I rocked for my few days surviving the humidity of the New York heat-wave.
Boat Shoe Trauma
I discovered boat shoes in high school in a socal beach town. I swear to god I had never seen anyone wear them before. I wore my Sperry Top-Siders religiously until I went to college on the East Coast and realized they were the default uniform of fratty athletes with allegations. I put them away and thought no more until I saw the new iteration by Morjas.
Buttery, pebbled leather, and minimal styling - I decided to give them a try this summer and have really enjoyed them. Especially with the chunky leather laces tucked away under the insole, they feel sophisticated with a mid-wash jean and are easier on the dogs on hot days than stiff loafers.
Polo Shirts
This one might seem backward to you, especially because the polo has got to be the least adventurous style choice of all time, but for most of my life I’ve hated them. I looked down on them (and their wearers) as cowards, but maybe I can thread the needle just so and make one work.
I ran into a woman in Ojai recently who remembered me from my “short sleeve polos suck” content and I felt I ought to reflect on that stance. Some long sleeve knit and even short sleeve bouclé version have crossed the rubicon into my personal wardrobe, but the cotton piqué polos are still tough for me.
I did, however; find a 100% linen navy polo from Ralph Lauren that I wore a bit during my travels. I liked it for its breathability, but it still didn’t quite do the trick. I’ve decided my heart is open to the right polo as long as it’s 100% cotton, vintage Ralph, and fits me real tight and sexy. (The sizing on the vintage market is tough, every one I’ve found so far has been a little too big, which makes it not so sexy.)
Doubling Down on Dainty
Coming from the world of vintage Americana, I believed everything had to be real big and beefy. This school of thought gets broken down pretty quick when you’re fighting heat-stroke in some foreign (but glamorous) context. The fashion élites tried to convince us that guys needed ballet flats, but I wasn’t biting on that particular school of shoe
Morjas once again enters the chat, this time with a Belgian loafer. Toeing that line between shoe and slipper, I think can pull this one off. I’ll be trying them out while I have a post-work spritz in Florence this week.
In Conclusion
You bring the personal and time brings the style. Pull inspo hither, thither, and yon and see how it makes you feel. Best of luck, dear friends.
To me, personal style is important, but the sole definition is that it's things I enjoy, and that is ever-changing.
This year I'm leaning much more 70s. Big square glasses, facial hair, trucker caps, and so on. It's a bit corny but that's exactly what makes it fun. I also finally embraced socks with shorts, athletic stripes and all. Two years ago these would have been outside of my style wheelhouse.
Part of style, like you said, is exploration and growth. To me, it's self-expression. I like my style but it would be boring if I just stuck to whatever some dude on the internet said is acceptable.
Like shorts, for example. I still see that archaic “shorts are for young boys” nonsense being parroted around, but I think it's just that men are often self-conscious about showing their legs. Too bad for them I guess. I get to stay cool and explore all the fun variations that are out there.
I might even get into the super short athletic type with the contrasting trim. Might be outside my comfort zone, but at least I'm not beholden to the so-called rules and can try them if I want to. Would I look like a slutty summer camp counselor circa 1978? Probably, but as long as I'm following my curiosity and having fun that's all that matters.
My father and grandfather say, “Dress for the person you want to be. Wear what fits well and feels comfortable. Style is the outcome of knowing yourself (values).”