My Fashion Mistakes & What I Learned

To sum up the entirety of my style evolution, I can say one thing: it was a lot of mistakes, a lot of learning who I am and then being comfortable with who I am through fashion. Though luckily for me, I was brought up in a household with lots of W Magazines (rife with nipples and all, gasp!) and one very elegant grandmother. So despite the fumbles and ever-so-awkward experiments, I feel like I always knew where I wanted to end up….eventually, after I sashayed my way though girly, skanky, hippie, biker chick and all of the other horrible, “just not me” looks.

Let’s start this journey in junior high, around the time that I started to care about dressing well and fashion started to mean something more than “anything sparkly”. So prepare to laugh, be horrified and (maybe) recognize a little of your own evolution as we traverse mine and I impart what I learned about myself along the way.

Junior High School

I don’t have many photos from this time period, probably because we were still using the Kodak disposable kind of camera, but I’m sure that’s a good thing. From what I remember, middle school was about trends, so you gravitated towards whatever your friends were wearing. And junior high is where you start to branch out a little and begin to define style for yourself. I remember crimped hair, a love for graphic tees that lasted throughout high school, and hot pink lipstick all day, every day.


  • Stop tweezing your eyebrows! Leave them alone!
  • I look better in, and prefer, small prints (see GIANT print, above photo)
  • If you feel strongly enough about something to put it in writing across your chest, you should just say it out loud and not invite people to stare at your boobs.

WHAT I DID RIGHT: Not much, but I do love that I was a fan of button-ups peeking out of my collar, even then.

High School

To me, high school was having one foot in with everyone else and staying true to your self with the other. When you go to school with the same people everyday, you can’t help but notice what they’re wearing. In a way it’s cool, because you’re using every one else’s sartorial decisions to define your own. But if you also had a mom like mine, your clothing budget was small and most of your choices include input from her. Like, A LOT of input. So it was also hard to really be yourself and I think that, often, I was just rebelling.


  • My mom told me OVER and OVER, I can’t wear pastel colors. She was right, but that didn’t stop me from trying it 100 times until my crowning travesty, the pale blue gown (see above).
  • I also learned that I could express my individuality in what I wore, but was still holding out for the grownup budget and needed a little freedom from others’ opinion.
  • Lastly, I left denim cut-off skirts/shorts/anything sheared behind. But no shame here, I went to high school in the middle of small-town Louisiana, what else was I supposed to wear?

WHAT I DID RIGHT: I phased out of tom-boy chic and embraced being girly to the max. I mean, that SCREAMS PINK ball gown (see above)!! Am I right??! Still love it. Wouldn’t be caught dead wearing it, but it’s just so perfect for a young girl with a lot of chutzpah, but not much taste.


Coming from a Catholic high school, and middle school and pre-school, going to college was FREEDOM in bad ways and good. It was wonderful getting to wear whatever the heck you wanted, but as most girls can attest, there were days you missed the simplicity of a uniform. And while I did a lot of dragging myself around hungover and displaying my magnificent décolletage, a real turning point in my style evolution came when I started making rules for myself. It was second half of my sophomore year and I had been feeling low for a long time, so I decided I would start dressing better and “fake it till I make it”, as my mom always says. Which meant never wearing work out clothes (unless actually going to work out), always having my hair done (even if that meant sticking it in a bun) and putting on a little makeup before going out. The effect was immediate! My girlfriends, and even one guy friend, noticed and complimented me on the fact that I always looked put together. Hooray! Bucket list item #45 complete!

So while there was still a great deal of messy experimentation going on, this was the time period where I learned the most about what I wanted my relationship with fashion to be. And it didn’t hurt working at J.Crew my senior year with all the goodness of an employee discount.


  • Seriously, stop with the pastels.
  • People respect you when it looks like you respect yourself.
  • Leopard is for accessories (and maybe an overcoat). Not for dresses, pants, shirts, etc.
  • Boys get the picture with a nice bit of cleavage out OR long legs. They don’t need both and let’s be real, it’s more than they deserve.

WHAT I DID RIGHT: Experimented without shame and started setting guidelines for myself, which made it quicker and easier to get dressed in the morning. Also, I look great in red. Which is good, because as a Chi Omega, I had to wear it over, and over and over 🙂

Adult Life

I think my biggest mistake as an adult thus far, is buying one item of clothing at a time. Or buying a bunch of single items at a time, but never focusing on building an entire outfit. I certainly have gotten better at making sure everything that I buy goes with something else in my closet that I already own, but I’m working on buying full, complete outfits or being able to assemble them with what I already have. This is a quicker way to create a closet filled with tiny capsule collections, and makes it easier to get dressed, though it may seem more expensive. But I think the easiest way to feel like you ALWAYS have something to wear, is having a lot of pieces that compliment one another. If you have a lot of single items that only go with one outfit, then of course it feels like you have nothing.

Overall, I think discovering who you are through fashion is a lifetime journey. But it’s a fun journey and, done the right way, a great way to build confidence. While my pocket book doesn’t appreciate experimentation, I hope it’s something I do anyways. In the meantime, I’m looking forward to fewer embarrassing photos and being able to get dressed at speeds that continue to impress LIL (my live-in lover).