Let’s Be Real About Fashion
Okay, full disclosure: I’m not some fashion guru who’s always been on trend. I’m Jenny, and I’ve spent the last 20 years making mistakes, learning lessons, and occasionally getting it right. I’m the girl who wore socks with sandals in 1998 (don’t judge), and I’m also the woman who rocked a killer outfit to the Met Gala last year. Fashion is messy, and so am I.
I started my career in 2003 at a tiny magazine in Chicago. My first assignment? Covering a fashion show. I showed up in jeans and a t-shirt, thinking I was being edgy. The designer, let’s call him Marcus, took one look at me and said, “Honey, you’re here to learn, not to teach.” Which… yeah. Fair enough.
Why I Hate the Word ‘Trend’
Look, I get it. Trends are what sell magazines and fill Instagram feeds. But honestly, I think the word is overused and misunderstood. Trends come and go, but style? Style is forever. I mean, think about it. How many times have you seen a “new” trend that’s just a rehash of something from the ’80s or ’90s? Exactly.
Last Tuesday, I had coffee with my friend Lisa. She’s a stylist, and she was complaining about how clients keep asking for “the latest trend.” I told her, “Lisa, trends are like fast food. They’re quick, they’re cheap, and they leave you feeling empty.” She laughed, but I was serious. Fashion should be about expressing yourself, not following a script.
The Time I Wore the Same Dress Twice in One Week
Okay, this is gonna sound crazy, but hear me out. About three months ago, I wore the same dress to two different events. The first time was a casual brunch with friends. The second time? A fancy gala. And you know what? Nobody noticed. Well, nobody except my colleague Dave, who said, “Jenny, that’s the same dress.” I looked at him and said, “Dave, it’s a black dress. It’s versatile. Deal with it.”
Here’s the thing: fashion doesn’t have to be expensive. It doesn’t have to be disposable. It can be smart, it can be sustainable, and it can be fun. And sometimes, it’s okay to wear the same dress twice in one week.
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The Great Heel Debate
I have a love-hate relationship with high heels. Love them because they make me feel tall and powerful. Hate them because, well, they’re torture devices. I remember this one time in 2015, I wore these stilettos to a conference in Austin. By the end of the day, I was limping. My friend Sarah took one look at me and said, “Jenny, why do you do this to yourself?” I didn’t have a good answer.
But here’s the thing: comfort doesn’t have to mean sacrificing style. There are alot of great options out there for comfortable, stylish shoes. And if you’re gonna wear heels, for the love of all that is holy, invest in some good insoles.
On Being a Perfectionist (And Failing Miserably)
I used to be a perfectionist. I thought every outfit had to be flawless, every accessory perfectly chosen. Then I realized that’s not only impossible, it’s also kinda boring. Fashion should be about expressing yourself, not about being perfect.
I remember this one time in 2010, I spent hours getting ready for a party. Hair, makeup, outfit, accessories. I looked good, but I felt like a fraud. My friend Marcus (yes, the same one from earlier) took one look at me and said, “Jenny, you look like you’re trying too hard.” And he was right. I was.
So I made a committment to myself: I would stop trying to be perfect. I would embrace my imperfections, my quirks, my unique style. And you know what? It was liberating.
Final Thoughts (Or Lack Thereof)
Fashion is messy. It’s chaotic. It’s personal. And that’s what makes it so damn interesting. So go ahead, wear the socks with the sandals. Mix patterns. Wear the same dress twice in one week. Just be you, and have fun doing it.
And remember, fashion isn’t just about what you wear. It’s about how you live, how you feel, how you express yourself. So go out there and make some fashion mistakes. Learn from them. Laugh about them. And most importantly, have fun.
About the Author: Jenny Thompson is a senior magazine editor with over 20 years of experience in the fashion industry. She’s written for major publications, covered countless fashion shows, and made more than her fair share of fashion mistakes. When she’s not writing, you can find her exploring the streets of New York City, searching for the perfect vintage find.
