For most of my early life, there was nothing I dreaded more than going shopping for clothes.

The whole process reminded me of how awkward I felt in my own body. You only had to take one look at teenaged me to guess that fashion ranked pretty low on my list of priorities. While my peers sported the latest Abercrombie, I rotated through my punny T-shirt collection, week after week.

A lot has changed since then (except my sense of humor). Over the last decade, I have developed a personal style that I love. Here’s how I did it — and what I learned along the way:

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Lesson #1: You must believe you’re worth the effort.

Looking back, I realize that my resistance to fashion wasn’t really a matter of disinterest or defiance, but something else entirely: a lack of confidence.

I didn’t believe that I deserved to wear beautiful things, because I didn’t feel beautiful. I didn’t want to draw attention to myself with the clothes I wore, because I didn’t feel deserving of that attention. What if I tried to wear nice clothes, and I STILL looked bad? It felt safer to not try at all and chalk it up to a lack of effort.

Once I allowed myself to sincerely try, I found that fashion has actually enabled me to recognize and celebrate my beauty.

Lesson #2: Pay attention to the pieces that make you feel great.

In college, I met my fashion fairy godmother in the form of my roommate. She wore cat-eye glasses, miniskirts, patterned tights, and velvet Doc Martins. She could make even the most basic student organization T-shirt look like a cool thrifted find.

It all started with one skirt.

One day, we ventured to a boutique in Westwood. My roomie helped me pick out a floral miniskirt that made me feel quite pretty, which I hadn’t felt often.

The thought of reinventing your style can feel especially daunting if you try to tackle it all at once. I’ve learned that it all starts with one piece. For me, it was the skirt, and that one skirt gave me a direction to shop in.

As you can see in these photos, I really leaned into the floral:

Then, on my 19th birthday, I walked by a kiosk at the mall and spotted a black, wide-brimmed hat. I’d never considered adding accessories like this before, but once I tried it on, I was hooked.

Now, I have a bin of hats and headbands. Again, it all started with one piece.

Lesson #3: Don’t be afraid to turn heads.

In high school, I’d trudge around campus feeling invisible. If I received attention, I assumed it was because I did something to embarrass myself.

One day, in college, I walked to class in the outfit pictured below. I got a lot of double takes, so many that I grew a little self-conscious. Most people attended class in loungewear. Maybe this was too much, I thought.

When I arrived at the lecture, I sat down next to a new friend and whispered, “Please be honest. Do I look ridiculous?”

“No,” he said with a smile. “You look amazing.”

A lightbulb went on in my head and, ever since, I’ve intentionally used fashion to help me take up space and assert my presence. I realized that for me, being stylish isn’t about fitting in; it’s about standing out.

Lesson #4: You don’t have to pick one look.

Below, I’ve featured some of the outfits I’ve worn over the last few years. Each outfit exudes a distinct character and energy, and yet, I believe they all feel distinctly me. I don’t think developing a personal style must mean you have to create a uniform for yourself. (Unless that’s what you want. To each their own!)

Experimentation can enable you to add new flavors into your wardrobe, to keep it fresh and interesting. One day, I’ll be in a polished blazer and slicked-back bun. The next, I’ll rock a leather jacket and combat boots. And then I’ll throw on a flowy sundress.

Lesson #5: There’s no such thing as “overdressing.”

The occasion may only call for a ratty T-shirt and leggings, but if I feel like a denim jumpsuit will make me shine brighter, I’m going to wear the darn jumpsuit! Not to mention, my best outfits are usually the ones where I momentarily ask myself, “Is this a bit much?” (That’s when I know I’ve got it right. 😉)

After all, why be ordinary when you could be extraordinary?

I’ve never regretted a good fit, but I have regretted missing an opportunity to show off a good fit.

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I hope this lil’ blog can provide encouragement and inspiration as you develop your own personal style. If you have any insights to share, I’d love to hear them in the comments below!

Till next time,

Jo