The Evolution of My Personal Style

Anna R.
November 9, 2023

From Fran Fine's inspirations to dressing for the “butch gaze,” my style is constantly evolving. It’s taken me years to find a style that accurately reflects my identity. But I think after 30-something years, I’ve finally found it.


I've loved fashion and style for as long as I can remember, and yes, there is a distinct difference between the two. Fashion was the thing I read about in magazines, something that I never thought I could attain as a fat working-class child growing up in the Midwest. Style was something I could embody; it was tangible and eventually became an integral part of my identity. Throughout the years, my style has changed and evolved, and I'm sure it will continue to do so. Let's reflect on my personal style evolution and how I came to my current philosophy. As always, take what resonates and leave what doesn't. And above all else, dress for yourself. 

Childhood: Fran Fine Wannabe 

I grew up with one of the most iconic fashion inspirations a girl could ask for: a Nana (great grandma) with impeccable taste, lots of disposable income, and a deep love for matching sets. Her closet was full of matching sets, suit sets, sweater sets, matching purses, and shoe combos; if it matched, she had it. Luckily, her affinity for matching sets has deeply imprinted on me, and I honestly can't deny their power. Where I deviate from Nana Trudy is our execution of sets. Today, I primarily favor sets that lean just a bit kitsch with impeccable tailoring; think Fran Fine, another deeply imprinted fashion influence. 

Trudy also loved big clip-on earrings, black-and-white color blocking, chunky heels, and a full face of makeup. I was blessed to grow up with my Nana in good health, and I would occasionally get to go to work with her. Every day, she would drive into downtown Chicago in the world's widest Cadillac, a matching suit set, chunky heels, and vivid eyeshadow. She smelled like three bottles worth of the White Diamonds by Elizabeth Taylor fragrance mixed with fresh cigarette smoke. I admired every bit of her; her fashion was just part of her magnetic and dynamic personality. When I was lucky enough to "go into the office" with her, she insisted I wore a matching suit set too. 

I loved exploring the offices and seeing what all the corporate professional women wore. Sometimes, they would even let me try on their Prada and Fendi bags. I'd thumb through the fashion magazines in the break room, dreaming of something big for my future. 

At times, it was difficult to live up to how incredibly polished my Nana was, and some strains in our relationship came with that. But in retrospect, I am extremely thankful for everything she taught me about fashion, life, and the art of entertainment. She impressed the importance of presentation and quality execution. Something that has pulled into most of my fashion choices and has made me invest in a good quality tailor. 

Late Childhood: Music Enters Style 

Like every other truly creative genius, I’m a product of divorced parents. When I was about five years old, my mother started dating who would become my eventual stepdad, Aaron. He was cool, but not just cool, like COOL COOL. I had never met anyone like him, he dressed in all black, seemed to know everything about music, and I thought he was really silly. I deeply wanted to emulate him. How could someone so “dark” still be so cool and silly? While I don’t quite know how Aaron would define his style, I really don’t think he would describe it as one thing; he was too cool for that. He took references from 70s David Bowie, 80s Duran Duran music videos, and many other incredible musicians. 

He eventually moved in, and our apartment became packed with music equipment, mostly synthesizers and production equipment. The rumor was always that he used to play music with Billy Corgan of the Smashing Pumpkins before the band's creation. A story I do believe to be true, given his weirdly personal beef with Billy Corgan. While my mother and Aaron divorced a few years later, Aaron’s fashion and musical knowledge deeply impacted me. It ignited my passion for music, it gave me an outlet for all my anger and sadness, and it forced me to think more creatively. I really do believe Aaron made me cool by teaching me to not give a fuck what anyone thinks of you. Every time I listen to Gary Numan, I am reminded of his incredible energy.

Teens: Mall Goth Gone Pop Culture Crazed 

I didn't know who the fuck I was when I was a teenager. I had many different fashion aesthetics; I just wanted to play and rebel. I went from wearing Tripp chain pants as a mall goth to a pop punk band tee-wearing wannabe to a failed scene queen and, most bizarrely, a knockoff of Blair Waldorf. I was always incredibly inspired by music and magazines. I'd spend hours looking through the editorials, only to dissect them and turn them into massive collages. I didn't believe in leaving a single space on my wall uncovered. I loved them all, from Kerrang to Alternative Press, Teen People, Seventeen, and Teen Vogue. 

But my life changed when I got my hands on Nylon magazine. Overnight, I decided I needed to emulate everyone in that magazine. It perfectly encapsulated music, fashion, and culture in a way that deeply resonated with me. It's worth noting that at this point in time, celebrity culture was at an all-time high. Lindsay's stolen Birkin, Paris's post-jail paparazzi walk, and Nicole Richie's infamous Memorial Day party invite. I was obsessed with anything pop culture, in particular, the grittiness of it during that time. But Nylon was helping me gear up for something bigger, my dirty hipster era. I just wanted to express myself in the most shocking, nonsensical way possible. 

Late Teens to Early Adulthood: Too Fat for American Apparel 

Yeah, I was a hipster. Jealous? I spent most of my time listening to music (The Gossip, Crystal Castles, Peaches, TV on the Radio), reading through Nylon magazines, obsessively checking my Tumblr, and doing lots of other things I had no business doing. I was also exploring fashion blogging and taking inspiration from my favorite plus-size bloggers. Body positivity was starting to come into the conversation, and I felt empowered, even if body positivity's self-appointed leader was scamming her fans... allegedly, of course. Like many in the movement, I pushed to wear things that I thought would be "unflattering," and I didn't really care. I loved spandex disco pants, 80s grandma sweaters, tight bodycon dresses, and, unfortunately, vests. I realized the most incredible things could come from the most unexpected places; almost anything can be fashionable if you make it your own. 

During this time, I started to get hyper-concerned about flagging as Queer. I can recall it being the first time I ever felt insecure about how femme I was. I got an undercut to prove myself. I was sneaking into every Chicago lesbian bar I could and would get so incredibly disappointed when no one would hit on me, I felt like a big Queer failure, and I broke my own rule. I stopped dressing for myself.  I started to dress for the butch gaze in ways I thought others would see me as Queer. Now that I have a fully formed frontal lobe, I realize no one was hitting on me because I was a baby-faced 19-year-old and not because I was too femme. Oops! 

Adulthoodish: The Instagram Identity Crisis 

To be candidly transparent, fashion has always been a shield for me, and I imagine some fat people can relate. If I looked perfect, "they" would have to respect and value me. Mix this insecurity with Instagram, and my overconsumption era was born. I started buying a lot of fast fashion, buying things only to have them sit in my closet for months and then sold or given away. While I didn't have the biggest budget back then, I was focused on quantity over quality. 

I needed someone to compliment my outfit every time they saw me, or else I would die inside. I bought anything just to feel something, to be seen as cool, to show off something new (I was making fashion content). I wanted so badly to be seen as cool that I lost any sense of my personal fashion. I would wear outfits that would get me the likes (re: validation) I desired. What came out was a product that was so untrue to me. But we all get lost at some point. I appreciate having doubt in myself, for the beauty of feeling lost, and realizing that no matter how I look, some people will never respect me, so I should focus on being happy with myself. 

Today: The Corporate Goth Kinkster Fran Fine

It’s weird; I know they say your frontal lobe forms at 25, but I think maybe I had a delayed reaction. It’s like I just woke up at 28 one day and said fuck it, let’s do something different. I was tired, really fucking tired. I was tired of everything in my life, my shit whore job, my lack of a corporate career, my physical health, and quite candidly, even some of the relationships I had in my life. I knew who I wanted to be, and I knew I needed to change to be that person. But I’m a Taurus, so change is hard for me.

So I started with getting the fuck off social media and getting back to my favorites, music, and magazines. I took other things in my life, like my physical health and career, more seriously. I focused on remembering when I felt the most myself in my life. Turns out, that was childhood. Which I imagine is the same for most people because, as a child, peoples shit opinions and projections aren’t beat into you yet. I started making more collages again, pulling images from architecture, art, and music magazines. I started remembering all the things I loved about all my fashion influences. Their magnetic personalities, the joy they radiated, and perhaps most importantly, their unapologetic nature of existing as their whole selves. And so here I am, a 30-something-year-old corporate goth who loves a kitschy matching set, quality leather goods, and impractical (but beautiful) footwear. 


So, let's get to my fashion philosophy. Again, this is just my own and what works for me. I don't think anyone has to emulate it or should. 

After years of overconsuming, something clicked: I had to start caring about quality. It started from wanting to look more polished, which led me to learn more about fabrics and a 101 understanding of the production chain. I started investing in quality pieces I could see myself wearing in multiple ways. My actual clothes have more traditional silhouettes, and accessories are where I can play. My favorite accessories are checker print trunk bags, big acrylic cocktail rings, and harnesses

I also subscribe to a cost-per-wear theory. This, if you aren't familiar, is essentially the idea that while the upfront cost of an item may be high, if you intend to wear it often (AND DO), it will have a lower overall price. Looking at my clothing this way helps me think critically about my consumption. If I can't think of five places or ways to wear the item, it doesn't get bought. Exceptions are made if the item is obsessed over for the next month. 

Over the pandemic, I started wearing all black again, or mostly black; I also adore black and white colorblocking. I started dressing in all black again because I'm just a kinky goth. When dressing monochromatically, I think about the individual pieces. I make sure that there is enough texture and fabric to make things visually interesting. I love monochromatic dressing, but without visual interest and some classing, things can get boring. 

So, the takeaways? Fun textures, classic silhouettes, and statement accessories are my principles. Invest in a good tailor, and anything is possible. Quality over quantity. Look to culture (music, movies, runway, celebrity) for reference. Fail sometimes, but have fun doing it. And most importantly, dress for yourself.