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Ranking My 10 Most Memorable Hair Eras From Worst To Best (With Pics!)

Holly Thompson Student Contributor, University of Connecticut
This article is written by a student writer from the Her Campus at U Conn chapter and does not reflect the views of Her Campus.

I’ve had quite a few odd haircuts and have dyed my hair several times. I’ve learned a lot from these experiences over the years. I reflected on these different looks while writing this article and have ranked them on a scale of 1-10, with #10 being the worst and #1 being the best. I hope that you can learn from my mistakes and don’t feel nervous to switch up your own hair (but love it naturally, of course). Enjoy! 

10. Worst haircut I’ve ever gotten

My least favorite haircut
Original photo by Holly Thompson

In my junior year, after finally growing my hair out from the big chop of 2022 (I’ll mention that later), I got the most atrocious haircut of all time. I asked for no layers; I’m lazy, and I didn’t want to spend time making sure they were styled properly. Unfortunately, the person who cut my hair did the opposite of what I wanted. She essentially cut half of my hair into a bob over the rest of my hair, which remained the same length. I have barely any photos of it because it looked SO bad, so these pictures don’t do it justice. You’re gonna have to trust me on this one. 

9. Dying my hair orange and low-key bleaching it by mistake

When I accidentally dyed my hair ginger
Original photo by Holly Thompson

This was such a fever dream. My best friend Natalie, shoutout to her, dyed my hair red months before this, and it looked awesome (I’ll get into that one later too). However, this time, the employee at the hair dye store screwed me over. She told me to leave the dye on for way too long, gave me hair dye that did not turn color, she said it would, and said that it wouldn’t be a problem using the new dye over my already dyed hair (it was). So, instead of getting the dark pink color I wanted, my hair turned bright orange. This leprechaun era lasted a single day before I redyed my damaged hair. Truly a scary time.

8. You know that I’m known for the bob

My haircut from when I was younger
Original photo by Holly Thompson

The childhood bob is such a cannon event. Not much to say about this one. The bangs were kind of outrageous, but the bob absolutely devoured. No regrets, but definitely not my most iconic hairstyle. I served regardless.

7. The big chop of 2022

My super short haircut
Original photo by Holly Thompson

When I initially cut most of my hair off, I loved it. They styled it perfectly at the hair salon, and it had its cute moments. It definitely wasn’t bad, but it certainly was not the best. As I said, I’m lazy with hair, and I didn’t take the time to style it properly. So, while it had potential, I usually didn’t live up to it.

6. Taking it into my own hands

When I cut my hair off!
Original photo by Holly Thompson

Junior year was a tough time for me, and one night, I spontaneously decided to cut my hair with scissors that were definitely not meant for cutting hair. I was bored, alright? I wanted to switch it up. Shockingly, it managed to look half decent! I’d dare to say it was cuter and easier to manage than when I originally chopped it at the hair salon.

5. Long freshman year quarantine hair

My long hair from freshman year
Original photo by Holly Thompson

There was nothing wrong with this look, but it was a lot of hair to manage. It was way too thick, and I’d been growing it out ever since my childhood bob phase. This was the longest my hair had ever been, and since then, I’ve kept it either short or midlength and slightly more thinned out.

 4. Successful hair dye fail

When I accidentally dyed my hair black
Original photo by Holly Thompson

The first time I tried to dye my hair, I used a dark purple dye, but since I started out with brown hair and didn’t bleach it, the dye just made my hair darker. However, I actually loved how it turned out. It was closer to black than purple, but it’s one of my favorite hair colors I’ve had.

3. Red hair eras

My dyed red hair
Original photo by Holly Thompson

I love a good red hair dye. My friend Natalie dyed my hair dark red, my first successful hair dye attempt, and I loved it. It was relatively subtle while still being noticeable. Later, after I dyed my hair orange unintentionally over the faded dark red, I had it dyed purple/red at the salon. That is the current color of my hair. I hated how bright it was at first (as you can see in the first picture), but it has toned down since then, and I’m happy with it now.

2. That perfect mid-length cut

My midlength hairstyle
Original photo by Holly Thompson

My favorite hair color and style is my natural brown hair, cut mid-length. You can’t go wrong with this look; not too short or too long, and embracing your real hair color. Over the summer, I plan to dye my hair back to brown to achieve this look again and go back to my roots (literally).

1. The double stage

My iconic hairstyles from when I was younger
Original photo by Holly Thompson

Okay, I lied. My REAL favorite hair stage has to be when I was obsessed with wearing two hair pieces at the same time. I used to wear two hats or two headbands at the same time, and say I did it because my initials spell H.A.T. I was just an indecisive child. This is so funny and stupid to me, so it has to take first place. Literally WHAT was I thinking?! Not much, I guess.

I had such a fun time writing this article. I hope you’ve enjoyed these hair-raising absurd photos and stories, and I wish you the best on your own hair journeys. Don’t be afraid to try something new! Good luck, girlies. 

Holly (hall-ee) Thompson is a sophomore Journalism and Human Rights double major at the University of Connecticut. She is from Hopkinton, MA. Besides writing, she loves to sing, workout, go outside, listen to music, and spend time with her friends, family, and dogs (obviously). She is so excited to spend the next four years at UConn and get involved in the community. :)