How I Found My Fashion Aesthetic at 31

I used to hate every outfit I put together. Here's my guide for how I fixed that and created a style I love.

I recently wrote about how I taught myself social skills at 28. Well, I also taught myself how to dress well at 31. For those of you who aren’t familiar with how I dress now, here are a few examples (I’ll share more later on in this piece.) I’m aware some people will say I still dress badly (everyone’s a critic!) but that’s not really the point. I’m dressing in a way that makes me happy, where I always have something that I want to wear. That’s the goal!

Oh look, that was the outfit that the CHH wojack wore:

I had always enjoyed fashion, but was never very good at it. I define being “good at” fashion as having a cohesive style and aesthetic anways having something to wear that you like, since “good” style is pretty subjective. People who knew me when I was younger might say I was good at fashion then, and maybe I was for a bit—in high school, I feel like I had a really great cohesive wardrobe for the style of the time. I was inspired by manic pixie dream girls in romcoms, preppy J.Crew styles, and Rachel MacAdams in The Notebook. Most of all, you know a wide waist-cinching belt hated to see me coming:

Even though I generally liked what I had in my closet, I did have one insecurity which drove my fashion choices, which was that for some reason I was convinced that wearing anything statement-making would “freak out boys.” Blame Cosmopolitan articles about how all men like is a T-shirt and “good-butt jeans.” Every time I got a boyfriend or a new crush, I would retire my cute waist-cinching belts and dresses and wear long-sleeve tight T-shirts, low-rise flare jeans, and yoga pants. I almost looked forward to breakups because then I could dress like myself again. I know this is so silly in hindsight, but I was literally a neurodivergent minor.

CHH FACE REVEAL OMG

As I got older, I continue to balance my fashion tastes (which changed dramatically over time- let’s not dwell on my Club Rat Kardashian phase of my early 20s!) with whatever my insecurity du jour was. Usually, it was that I wanted to appear as a certain type of person to others—I wanted to fit in with the cool sorority girls at college (I very much failed at this, clothing notwithstanding) or I wanted to appeal to boys. Either way, there was always something holding me back from dressing in a way that truly made me happy. I would think that I was dressing in a way that made me happy, but after a few months I would look at my closet and wonder why I hated everything there when I had loved it all at one point.

The beginning of my true aesthetic journey happened around the time I got married. I was almost twenty-five, and I had been dressing in a style I can only refer to as “Sexy Pinterest twee.” It was 2014, so it didn’t look as dorky then as it would now, but when I went on a honeymoon with my husband in Greece, and saw all the other fashionable tourists and locals, I suddenly felt ridiculous in my Keds sneakers, ASOS fit and flare dresses, and stretch denim short-shorts. I mean, there was nothing wrong with dressing in a youthful and casual way, but I realized, upon seeing the much more risk-taking and elegant Greeks and tourists in their maxi wrap skirts, linen trousers and paisley scarf tops, that I didn’t feel comfortable dressing the way I was dressing. And there’s one major reason: it was fueled by a crippling insecurity.

For some women, they obsess over how skinny or fat they look and they wear clothes exclusively to make them look thinner. Unsurprisingly, they tend not to have very expressive or authentic styles because they’re focused only on their body size. My issue was similar. I was obsessed with a fear of looking old. I kind of have one of those faces where I have looked thirty since I was sixteen, and I can’t really explain it. I just have the opposite of a baby face. I’m totally fine with it now at thirty-five, because none of this has to do with premature aging (and even if it did, we all get old eventually!) but in my early twenties it was a huge insecurity. Whenever people would tell me they were shocked by my age, I always asked them why they thought I was so much older. And every time, they vaguely referred to my “styling.”

I sort of did dress a bit old prior to my Pinterest twee makeover, but not in a way that was frumpy or unattractive. I wore a lot of heels and tailored professional silhouettes which read as more mature than the go-to uniform for women my age around that time—Victoria’s Secret PINK sweatpants, flip flops, and a messy ponytail. A lot of the stuff I bought was marketed to older women, because I gravitated toward a more formal style. Take for example this outfit I wore when I was twenty-five, when a woman at my office cheekily referred to me as “robbing the cradle” when I mentioned my twenty-seven-year-old husband: