On the development of personal style

How I found myself through embracing self-expression and creativity

Introduction

The choice of what clothes to wear is such an interesting one. Putting clothes on your body is one of the most external forms of self-expression and creativity; some people are artists and share their creativity with the world, but most people only share their creative outlets with close family and friends, if at all. Not clothing though. Almost everyone puts on clothes before leaving the house. It is one of the only ways that most of us show the world who we are. You may not share with your coworkers or boss or strangers in the grocery store a photo you took or a painting you made; but you do show them your outfit. Even if it’s only a tiny fraction of your self-expression, you display who you are on your body—whether you intend to or not.

People are judgmental. If you are expected to wear a suit and tie to your job and you show up in a T-shirt, you will be consciously judged as underdressed. If you post that you’re wearing something very off-trend in an online fashion community, you will be consciously judged as unfashionable. And those are just basic examples of conscious judgments; strangers and friends alike will subconsciously judge your clothing as well. I don’t say this to frighten you, or to encourage you to dress in a way that you are fearful of judgment. I do not dress to blend in, to only follow rules, or only to avoid negative judgment from others. I encourage you not to do that either. That sort of discourse is perpetuated in some toxic internet circles; not here.

The real reason I brought up judgment is that the dichotomy of expressing creativity and personality through clothing, while also being judged for it, is incredibly interesting to me. It’s what makes personal style and clothing so important to me. I now understand that I dress to express myself, and to show the world who I am; I know that I am being judged, but I trust that if I am true to myself, then the judgment will be positive from those who are important to me. If others judge me negatively, so be it; I accept their judgment and do not let it bother me. The kind of people who would do this are probably not important to me in the first place. It is truly freeing to dress for yourself, and only for others in the sense that you hope they see who you are.

Function versus fashion is another dichotomy worth writing about and exploring. There are those who treat clothing as a purely functional practice; clothing is not self-expression for them, it is simply a barrier between the skin and the outside world. It is warmth and dress code only. That is perfectly fine. These people certainly express themselves in other ways. There are also people who believe that stylish clothing is not functional. While there are some examples of this (I’m not going to go around town wearing spray-on fibers like Bella Hadid at Paris Fashion Week), plenty of fashion is inherently functional, and this argument often comes from those who do not care to put in the effort to develop personal style. Again, that is all fine and well. But to be honest with you, at the core of it, most of the time, dudes just be wearing shirt, pants, and shoes. Nothing super special or inherently non-functional about it.

With all that off my chest, let’s get to the point. The purpose of this essay is to 1) describe the journey that it took to get me to my sense of personal style, and 2) share with you how to define and dress in a way that you find cool, self-expressive, and stylish. In this essay, I will not go deep into my own personal style; it’s not necessary for the scope here. However, I will be writing another essay soon, and I’ll update this sentence with a link to that if you want to check it out.

So, let's get to the meat of this essay. Before I can tell you how to find your personal style, I must share some things about my personal journey. First, it takes time. The process cannot be rushed. I started gaining an interest in personal style about 2 years ago, and, in retrospect, I have only been dressing like me for the last year or so. I've been cultivating and refining this more and more with time; the journey is far from over, but I am now at a place where I've learned some things and I want to share them. So, let's dive into my journey. 

The Basic Bastard and its consequences to those seeking answers in clothing communities and guides on the internet [2014 – 2022]

A little over a decade ago, like many others, I stumbled upon the r/malefashionadvice subreddit through some post that had made it to r/all. I had just finished high school and was entering my undergrad studies. I was going through a phase change in life. I was young, single, and stupid. I started college, I started weightlifting, I started going to parties. I wanted to dress better to elevate my social life (and dating life); I wanted to dress to be respected. I took the MFA guides to heart, and followed them as gospel, especially The Basic Bastard. Slim fit OCBDs; slim fit chinos in every color imaginable; hauls from Uniqlo; dark indigo Levi's that were so tight on my legs I blew out the crotch. 

The 2017 version of The Basic Bastard.

The "MFA Uniforms" which prevailed on the internet in this era (and are exactly how I dressed in ~2014-2017).

I want you to understand that the ethos of internet fashion communities was much different a decade ago than today. Everything was a guide or an infographic; there was pressure to conform to the guides; if you weren’t following the Basic Bastard guide, you weren’t cool. Trends were also different back then; dressing like the Basic Bastard wasn’t exactly trendy, but it was better than your average dude who didn’t know anything about clothing. It is exactly what it is meant to be: a thoughtless uniform to wear that doesn’t look bad, but is not self-expressive.

A note: I created my own, updated version of The Basic Bastard in 2023, during a period where I was still developing my own personal style. I think this updated version is better, less restrictive, and much more up to date than the old version, and I do not regret writing it, but, in retrospect, I am writing this essay in a manner of “making up” for writing that guide. I no longer want to tell people how to dress; I now want to help people figure out how they want to dress. Hence this essay.

So, what’s wrong with just dressing following a Basic Bastard or Basic Wardrobe guide? Nothing, if you’re okay with it. Again, developing personal style is not for everyone. But if you’ve read this far, I assume you’re either curious about developing your own style, or you are somewhere along the journey already. The Basic Bastard is not wrong to follow, but it is limiting; if you only follow guides for clothing, you will stunt your own self-expression by denying yourself clothing that you feel is cool. Instead, I hope that people who read my guide treat it as a stepping stone of sorts; a place to start, that’s neutral and inexpressive, where you can branch out in an interesting direction, or have some clothing to fall back on when you don’t know what to wear. This is why I haven’t deleted my own guide in frustration.

I was a Basic Bastard from about 2014 until 2022. This is a shockingly long time; however, I was not focused on personal style for most of this period. I lost interest in MFA and stopped reading it entirely around 2016-2017; I started dating my now-wife, and I finished undergrad and started grad school; these took tons of time and energy. Productive, rewarding, and amazing endeavors, but not ones that allowed me the time to focus on myself. Clothing (and artistic creativity, and self-expression in general) was not a priority; I was too busy to focus on myself.

I do not have many pictures from this era because I did not take fit pics at all, either for MFA or for me personally. Many pictures of me are lost to old phones bricking, and most pictures of me are taken by other people, not myself. But here are a few examples I managed to dig up:

How I dressed in my Basic Bastard era. Top left: Target t-shirt, black Levi's 511, minimal white sneakers™ (Common Projects Achilles cheaper alternatives—these ones were thrifted Nikes); September 2014. Top right: Alpha Industries parka, indigo Levi's 511, and Red Wing Beckman boots (not shown); October 2016. Bottom left: Uniqlo blackwatch flannel, black Levi’s 511, the same white sneakers; October 2015. Bottom right: Levi’s commuter trucker in olive, Uniqlo gray buffalo check flannel, Uniqlo air stretch jeans, Red Wing moc toes (I was only trying these on; did not end up buying, thankfully); October 2014.

Getting back into things, finding myself lost, and getting roasted by strangers on the internet [2022]

About two years ago, I began another major phase change in life: I finished my graduate degree and got married within a span of a few months. With my dissertation defended and my wedding planned, I found myself with a bit more time and energy. With this new stability, I also began digging deep into myself - something I hadn't done in years. I asked myself many questions, like who I wanted to be and what I wanted to do with my life. Answering these questions did not come quickly or easily.

At the same time, I started regaining an interest in getting back into clothing and personal style. I hopped back into MFA, looked at a recent WAYWT thread, and thought, “what the hell are these people wearing?” This was not the slim fit Basic Bastard MFA I was used to. These people were dressing… weird! Unique! I don’t understand it! I closed the browser window and thought that maybe MFA just wasn’t for me anymore.

But I was wrong. I went back and tried to read more and understand more; after all, if these outfits were highly upvoted, the community found value in them; and I trusted that there was something there. Around this time, I started posting fit pics to MFA. I thought I was hot shit; I thought my fits would be appreciated. I did not know that the community would immediately see them as outdated, Basic Bastard, “this dude read a ton of MFA in 2014-2016 and I can spot it from a mile away” outfits. I’ll also mention that I spent an embarrassing amount of money buying clothing in this era, most of which I do not wear anymore. Take it from me: go slow when developing your personal style. Stop wasting money on shit you don’t really like. I give myself grace for these “school fees,” and I have the privilege of having my basic needs fulfilled. But seriously, buy clothing slowly (in general), especially if you feel like you haven’t found your personal style yet.

But, posting fit was constructive, even though people on MFA were a little too nice, most of the time, to give me the criticism I needed to hear (“dude, stop dressing like you haven’t thought about clothing in a decade.”) There were occasions where I received some (mild) ribbing, or got shot down when I tried to draw comparisons between my bad outfits and others’ good outfits. This was harsh, but it was true, and I was aware I had a lot to learn from the weird, unique, interesting people who posted fit. I asked for feedback, and I got a little. I even reached out to some of them in DMs and got better, more personal feedback. The photos here are not good; my photography sense developed along with my fashion sense (you'll see below). These are also not good outfits, but it’s what I needed to do to get to where I am now.

How I dressed as I was starting to get back into clothing and starting to post fit on MFA. Top left: Gustin jacket, J Crew shirt, Levi’s 511, Thursday boots; December 2022. Top right: Gustin jacket, Gustin flannel, J Crew pants, Thursday boots; November 2022. Bottom left: Barbour jacket, Target henley, J Crew chinos, Oak Street Bootmakers loafers; November 2022. Bottom right: Taylor Stitch jacket, Target henley, Levi’s jeans, Rancourt ranger mocs; November 2022. Note: I now dislike the brand Gustin, and I now intensely dislike the brand Thursday Boots. More on this in the next essay.

Starting to learn [Jan 2023 – July 2023]

After enough feedback and enough browsing of inspiration, I finally started to try and figure out how I really wanted to dress. I began doing a bit of experimentation; copying other users, saving inspo pics, and, on rare occasion, putting together a half-decent outfit where my personality began to shine through. I created an MFA-specific alt account to post fit pics. I even began writing style guides, like the Basic Wardrobe post discussed above. I started thinking more and more about the clothes I wore and how I wanted to present myself. Don’t get me wrong, I was still posting a ton of bricks. But at the same time, I was finding myself. I learned a little about Ivy style and wanted to dress like that. I discovered I love wearing loafers. I started buying all of my clothing secondhand (I made a goal to buy only secondhand clothing as a New Year’s resolution for 2023; made it until July but broke it for a good reason; more on this in my next essay). I wrote a secondhand clothing guide, which I am still very proud of:

I saw others dressing in looser silhouettes and less slim pants, and I wanted to try that for myself. I even ended up in an inspiration album here or there.

While all this was happening, I started a Google Doc that really helped me start to nail things down. I had inspo, brands I liked, MFA posters whose fits really resonated with me, a cop list, and also a list of “stuff I’m not feeling” (workwear/heritage stuff, anything too preppy, etc.) This Google Doc helped me start to define what my style was, even if I couldn’t put my finger on it yet.

The Google Doc that helped me figure out my personal style.

Here are some outfits from this era. Looking back on these outfits, they are not awful; they are just not fully me yet. A work in progress. More intentional, but not yet focused. I started learning more about photography and being more thoughtful with some photos. I was making progress.

How I dressed as my personal style started to come into focus. Top left: Engineered Garments jacket, South2West8 shirt, Wings+Horns chinos, Alden loafers; January 2023. Top right: Universal Works jacket, Polo Ralph Lauren shirt, Brioni pants, Alden loafers; March 2023. Bottom left: Universal works jacket, J Crew sweater, Wings+Horns chinos, Alden loafers; January 2023. Bottom right: Levi’s shirt, Gustin tee, Patagonia baggies, Rancourt ranger mocs; April 2023.

Coalescence, growth, and a sharpening of focus [July 2023 – Present]

Posting fit on MFA kickstarted my sense of personal style; but what really helped me really light that fire, is that some weird stuff started happening with Reddit admins, and the MFA community moved off the subreddit and onto Discord. (Long story short, Reddit’s admins removed the entire MFA moderator team, who were protesting over reddit-wide changes. The mods were community stalwarts; when they were removed, the community at large followed. The MFA community now thrives on the Discord server, and the subreddit has not been the same since.) Being on Discord meant more talking to the community in a chatroom-like setting; more discussion of fashion with those who resonated with my personal style, more posting fit, and more getting feedback. It is here that I began to really feel like I was dressing like me. Dressing like Ben.

As I was doing this, I was also going through a period of self-discovery; in fact, learning how to style myself was an effect of this. As my image of who I am came into focus, so did my sense of how I wanted to dress; how I wanted the world to see me. I became less afraid to be my true self. I started loving how I dressed. I gained a new sense of confidence. I started growing out my hair. I took the lessons I’d learned regarding photography and used them to make better fit pics. I tried telling stories with my pictures; I stopped shooting with a barren wall behind me. The long story short is, I began to love myself, and unafraid to show the world who I really was. I ceased fearing being judged for being creative.

It took me so long to actually define my own personal style. I asked others on the Discord server; they didn’t know. I called it “soft gorp meets Ivy” and a number of other things, but I was never happy with the definition. Then, it finally came to me (and I'll discuss it in the next essay).

I couldn’t bring myself to choose just four photos to represent myself, so here are six.

The personal style that I’ve discovered for myself. Top left: Story mfg shirt, unknown shirt, Brooks Brothers linen shirt, Bronson mustard chinos, Rancourt ranger mocs; February 2024. Top middle: Yoshiyuki Konishi jacket, Brooks Brothers linen shirt, pearl necklace, Issey Miyake pleated trousers, Alden loafers; March 2024. Top right: Wythe hat, L.L. Bean barn jacket, Story mfg pullover, linen shirt, a bandana I stole from my wife, some Polo Jeans Co jeans that I ripped on accident then got patched, New Balance sneakers; April 2024. Bottom left: Wythe hat, vintage blazer, L.L. Bean shirt, milsurp OG507s, Alden loafers; April 2024. Bottom middle: Parks Project t-shirt, Polo Ralph Lauren shorts, Birkenstocks; April 2024. Bottom right: Kokun.in eco printed shirt, Story mfg t-shirt, Black Ficus linen pants, Kokun.in eco printed socks, Birkenstocks; April 2024.

So, now that you know way too much about me personally, how do you develop your personal style??

Not everyone needs to go on a soul-searching journey to figure out about themselves and figure out what to wear. Maybe you just want to put shit on. Maybe you’re just good at that, and that’s cool. But if you’re not sure of yourself yet and you want to figure things out about yourself, here’s what I’d recommend.

Post fit. It doesn’t matter if it’s good or bad. It doesn’t even have to be posted online. Just take pictures of your own outfits. I've posted and shared so many awful fits. Take fit pics, share them or don’t, but you must take them, or you’ll never see your own journey.

Write. Make a Google Doc of your own; write a version of this essay for yourself or for your journal; do whatever you need to do to process and understand yourself and your personal style. It is much more confusing when you keep it all in your head. Write down your thoughts, write down your favorite brands, and even write what you do and don’t like about your fits.

Discuss and research. Joining an online fashion community was essential in figuring out what I liked and didn’t like. Pretty much every brand I wear these days I found out through the MFA community. Collect inspiration. It is impossible to develop your personal style on your own; it is massively influenced by others (it's still yours, though). Check out brands that speak to you. Look at their lookbooks and socials. Ask communities about your style and see what you get if you bounce ideas off of others.

Put in the effort and take the time. This does not happen fast, and you can’t rush it. It does take effort. Everyone who dresses well has posted bricks and has purchases they regret. Be patient, and understand that this is a slow journey, and that nobody goes from knowing zero about clothing to having a unique and interesting personal style overnight, in a week, or even in a few months. This is a long process and I suggest taking it slowly. I especially suggest not buying a ton of clothing at the beginning of your journey, or you will end up with lots of clothing you don’t wear.

Listen to your heart, not just your brain. Fashion is not like an optimization problem where you can solve an equation and find a singular solution. Dress by feel; be vibes-based. You do not need to find the perfect, ideal pair of sneakers or the most cost-effective pair of raw denim or the highest quality to price ratio of leather boots. Well, maybe you do, if that is who you are. But try to prevent yourself from being overly cerebral about personal style. It may end up limiting your creativity and self-expression.

Find yourself. The hardest step of all. I didn’t know how I wanted to dress until I understood who I was. I accepted parts of myself that I’d been hiding from. I focused and spent time on myself. I poured my heart into creative outlets and figured out how my various hobbies overlap with fashion. I strongly believe that everyone has their own personal journey to make, and it is only along this journey, through plenty of self-expression, that a strong sense of unique personal style can be developed.

That’s all for now – you can catch me on Instagram or The MFA Discord to see more of my personal style, ask me questions related to this essay, or help figure out what personal style means to you.