Looking back at pictures, we tend to laugh at what we were wearing; muttering sentiments of “I can’t believe I wore that…was that really the style?”

Yet, my fashion choices bring me to tears.

Real, sad ones.

Why?

Friends, my old pictures don’t read “out-of-style.”

I was never IN style.

In 2005, one of my best friends came to visit me at the Super Bowl, (I was working for the Patriots).  She arrived at my hotel with an arsenal of adorable outfits, but I remember telling her quote, “while living in Los Angeles, I’ve learned that you just want to be, you know, unpredictable.  As in not matching.”

So we were diligent in our efforts that week…trying to look unpredictable at every party.

Sports Illustrated Party, Super Bowl.

In my defense, I used to look at runway fashion and think, “wow, I would never put that together.”

I’d later learn why I wouldn’t.

We all have gifts.  Dressing myself well isn’t one of mine.

When I moved to Los Angeles, I fully intended to be on-point.  This Missouri girl fell victim to Rodeo Drive, which didn’t do anything but put me on par with Britney Spears, circa ALL THE TIME.

I’d buy a great handbag and completely ruin it wearing it with ill-fitting tops and bad jeans.  Or, I’d buy great jeans and put a bad jacket with them and pair that outfit with an ugly scarf, aka “the finisher.”

I knew things weren’t clicking when in 2004, I wore cut-at-the-ankle Seven jeans and a blue Theory tank top with WHITE Aldo pumps and matching belt to an 80’s concert and got some genuine compliments.

We were in Kansas City, Kansas.

I later went through a shiksa phase.  I got asked out at a party by a well-dressed Jewish guy who knew more about Barney’s than Barney.

I once told him I was headed to the mall and he said, “you go to THE MALL?”

Noted.

So, I drove my Honda to Barney’s, which is next to Saks and by Neiman Marcus.

But I was from Missouri.

I missed the mall.

I went back to the mall and searched out brands that seemed Barney’s-like.

More confusion ensued.  I ended up trying, and even a few times buying, runway clothes.

I’m five three.

Years have passed and I’ve realized that fashion should be about you and how you feel most comfortable.  I like to look homeless, but carry a great bag.  I know that I feel best in gray t-shirts and boyfriend style jeans.  I like a heavy watch on my small wrist.

My hillbilly grandfather once told me that I looked like a “dressed up stick” and suggested I “make more money so I could afford to patch up the holes in my blue-jeans.”

I said, “you’re right,” and when my then-contract was renewed, I kept the jeans, went to Chanel and bought my mom a bag.

As predicted.