Serious Question: Is Personal Style Dead?

Lately I've found myself wondering: Is personal style dead? I mean, what does "personal style" even mean anymore? What if I love trends too much? What if I find the concept of having a uniform, well, boring? What if I feel like wearing jeans for a month straight and skirts the next? Would I be violating every rule of the journey to finding my personal style? (I clearly have SO many questions.)

As I was searching for an answer, I remembered: I should Insta-stalk Courtney Trop of Always Judging for inspiration. The fashion girl is well up there with the Carrie Bradshaws of the world on my roster of cool women who have nailed down this whole "no personal style" style vibe. Take, for example, the way she made a coat reserved for the fanciest of events work for a casual walk around town. Clearly the style rules do not apply for this fashion girl.

Which is why I wanted to chat when I saw her edit from AG’s latest drop, rooted in the concept of more than denim. The theme celebrates the women who wear the brand—who invest in pieces, may they be denim or not, that speak to their creativity, their personal aesthetic, and their most authentic selves. Trop showed us what more than denim means to her (which—spoiler alert—goes beyond blue jeans), and I finally had that "aha" moment when it came to some of my biggest questions about personal style.

How would you describe your style?

I don't like to describe my style because it's constantly changing every day, every year. I don't like to marry myself to anything or anyone, actually. It's easier to describe what my style is not: I'm definitely not over-the-top feminine. I do enjoy a beautiful dress, but I usually won't wear makeup or feminine shoes to make sure it stays true to my masculine personality.

An all-white ensemble is a good go-to in the spring and summer when you want to take a break from figuring out your "personal style." How did you approach it?

All-white is something I wear every season in a million different ways. This spring, I'm dressing more masculine, which is why I paired these AG ex-boyfriends with a boxy blazer. I think it's cool to walk into a really dressy event dressed way down.

What's your favorite thing about always having go-to denim in your wardrobe?

You know when you pull them on that they're going to be comfy and, most importantly, wear really well over the years.

Let's talk about denim. What silhouette do you usually go for, and what works best in your wardrobe?

The jeans always have to be baggy—really low rise or really high waisted. If it's light denim, it has to be super baggy. These Rhett jeans had that vintage vibe I was looking for."

Tell us about this deconstructed sweater. How does this style work with where you are in your life right now?

Lately I've been all about comfort—things I feel good in around my house. I like how tattered the sweater is, which guides it away from cookie-cutter preppy style and more toward a grungy vibe (just how I like it).

How do you approach shopping differently than you did at the beginning of your career?

I'm 31 now, so I shop for more eccentric pieces and ones with longevity. I want to buy pieces I can pass down to my future daughter, because I will have a daughter one day (I can feel it). I go straight for pieces I know I'll never get sick of and that are made to last, like the Mya red denim jacket, that offers an interesting twist to a classic piece. 

How has the way you approach your style changed over the years?

That's easy: caring less. It's easy to lose yourself a bit when you take blogging and your personal style so seriously, and that's something I'm learning to avoid. I think (and hope) being myself has paid off and will continue to pay off. I'm not trying to save the world or lives—I'm just trying to help girls and boys get dressed and feel good about themselves inside and out.

What about approaching the upcoming season with darker denim? How do you fit that into your wardrobe rotation?

This last look reminds me of Americana vibes. If I were a child in the '70s, I would definitely wear this look. I like it because it has touches of American heritage but doesn't give off overly preppy vibes, plus the seam down the Jodi crop modernizes it. Combining the darker colors is also my way of approaching spring in an unexpected way when pastels are trending right now.

Shop Courtney's Favorite Pieces