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Hair

My Hair Eras Tour Taught Me What Every Cut And Color Says About Me (And Maybe You Too)

My hair was pretty much held together by Olaplex and prayers, LOL.

Cheska Santiago

by Cheska Santiago

Published on Oct 21, 2025

Hair color and cut signifies a new eraILLUSTRATION: Kurt Villagracia

If Taylor Swift has her Eras Tour, I have my Hair Eras Tour (a.k.a. Hair-as Tour... get it? 🤓). Much like how she marks different chapters of her life through music, I've chronicled mine through hair color. Each shade was its own era—some bold, some impulsive, and all accompanied by the occasional existential crisis. There may not be surprise songs, but there were plenty of dye-stained towels (and shirts—sorry, mom!) and moments of "wow, what did I just do?" in between.

I swear, if you looked through my camera roll from 2018 to now, you'd think it belonged to 10 different people, lol. There's me with bleached ends, me with blue hair, me with breakup-induced impulsive pink streaks—and yes, me sheepishly dyeing it all back to black when I needed a clean slate (and was tired of the growing out phase).


Some people mark their life changes with journal entries or playlists; I've always marked mine through hair dye. Each color held a story: of rebellion, of starting over, of finding pieces of myself I didn't know I'd lost.

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So, here it is: my Hair Eras Tour, spanning from 2018 to 2025. Read on if you want to relive the chaos with me, pick up a few lessons for your own hair coloring journey, or just marvel at the chaos that is eight years of me experimenting on my own head.

I Tracked Every Time I Dyed My Hair Since 2018—Here's What I Learned

2018: The Bleached and Colored Ends Era

I was in my third year of college at the time, and of course, being at Catholic school, it had strict rules about having "loud" hair colors (a.k.a. anything that wasn't black or brown). I wanted to do something, anything to my hair, so I bleached the ends—I didn't know about toning back then, don't @ me—for an ombré look. While it wasn't exactly part of the "allowed" colors, the result was dark enough that I was able to bypass the Ate guards at the school entrance, LOL.

Eventually, I took it further and dyed the ends a reddish-pink hue when my fourth year rolled around. It was my first time ever doing anything super drastic to my hair, and I finally felt like myself. Due to the aforementioned strict school rule about loud hair colors, I'd wear my hair in a specific hairstyle that concealed the colored parts whenever I was on campus. It was tedious having to do that, but my new hair color made me feel powerful and cool—like I was carrying a secret with me that only I can reveal.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia
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2019: The Independent Era

After my hot pink tips, I started off the year with a fresh chop to get rid of my ends and had my hair dyed a low-key purple hue. In retrospect, it was v simple (the color was only fully visible when I stepped out into the sunlight—very Edward Cullen of me, I know), but it was big enough of a change for me at a time when I was still "rebellling" against school rules.

A few months later, I graduated and finally started working, and with it came a sense of independence I'd never felt before. What color should I do next? The possibilities were endless!

It felt like serendipity when the first article assigned to me was to write a review about the "milk tea hair" trend shortly after I got the job offer to be an Editorial Assistant at Cosmo. ICYDK, the trend was all about dyeing your hair a mix of warm and cool tones to represent the pearls and tea. I got my hair done at Piandré Salon, and I also asked them to cut my hair into a semi-pixie cut to fix the damaged ends after a failed DIY bleach sesh.

After a few months, I got bored with my hair—this will be a recurring theme you'll notice as we go along my article, lol—so I decided to dye it dark blue. I was originally inspired by the denim blue hair trend at the time, and I was pretty happy with how it turned out... even if I looked like Cookie Monster. It was the first time I wasn't following rules or blending in.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia
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2020: The Hot Pink Era

At the start of the year, I decided to dye my hair a shocking hot pink color. It was a "New Year, new me" kind of dye job, I reasoned. A last burst of pre-lockdown optimism, if you will. It was a bright, happy color, and I joked that it made it easier for people to spot me in the crowds, despite my height, LOL. This kind of pink would end up being my signature hair color in the years to come, something I'd always come back to when I didn't know what to color my hair next.

A few months later, the pandemic happened. I stuck with my hot pink hair and didn't touch it until the next year—partly because of restrictions, and also because I was just in a constant state of paranoia about the world and restlessness.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia

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2021: The Color Roulette Era

This was the year I fully decided to lean into change. First, there was my unicorn-esque periwinkle hair. Stud and Sassy Salon reached out to Cosmo for a feature on their at-home salon service, and of course, I was the willing and game participant. (Shoutout to my teammates for always nominating me for these things—they know me so well, lol).

Since I knew I was going to be in professional hands, I decided to try a lighter color. It was the kind of hue I'd never dare to DIY myself to this day, since I knew I'd have to do multiple rounds of bleach to get my hair light enough for the dye to even stick. After almost an entire day and five(!) rounds of bleach later, I ended up with an ashy, pale purple hue with hints of silver.

I was in love.

Bored with working from home, I decided to do something drastic to my hair after my periwinkle era. I decided to do two-toned hair—one side was purplish-pink, while the other was neon blue. I used a mixture of Lychee Pink and Fuchsia Pink from Lunar Tides and Mermaid from Manic Panic to achieve this look.

It was my first time DIY-ing something that wasn't just one color, and I was pretty happy with the result—even if I personally felt like I didn't ROI it enough because I was just at home and I wasn't the assigned "tribute" of our household. (That's why I was extra happy whenever we had to turn our cameras on for work meetings, haha!)

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia

After deciding I was done with my two-toned era, I dyed the neon blue side of my hair with the same purplish-pink color to make them uniform. It was a nice change from my Harley Quinn era, I must say. Even though it wasn't the hot pink I used to like, it was a welcome change for me since I was able to ROI it a bit more because the restrictions were starting to ease up a bit.

In the months to follow, after deciding I was bored with my hair (yet again), I did teal, lilac-pink, then purple. My hair was crying for help at this point, but honestly, I've never been happier. "Olaplex at dasal lang talaga," I would joke at the time.

I liked being able to change my appearance whenever I wanted in just a few hours. I was spending every waking moment at home, feeling stuck and burnt out, so this became my little freedom.

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2022: The Hot Pink Comeback Era

After my era of experimentation in 2021, I returned to hot pink—the shade that always felt like home. There was something grounding about it. I no longer needed to shock myself with newness; I just wanted to feel like me again.

This was my only hair color that year because work was picking up again—our office was steadily implementing the RTO system. The only changes I did were getting trims here and there to slowly get rid of the pink inch by inch until I was back to black. Which leads me to...

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia
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2023: The Breakup Bangs (But Make It Bleach) Era

I went through a lot of things in 2023, which meant it was the perfect time to do something with my hair yet again. This was the year I went back to being a full-time Cosmo girl after spending nearly two years working with Candy Magazine. It was also the year I went through a rough breakup and ended my five-year relationship. (Oof.)

Most people get bangs or haircuts after a breakup, but because I'm me, I decided to bleach my front pieces and dye them pink on a random Monday night before work the next day. It was impulsive, emotional, and exactly what I needed.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia
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2024: The Back-to-Black Era

After years of putting my hair through the absolute ringer (RIP to my tresses 💀), I decided to color my hair back to black and let it grow out. It was also during this time that I entered my current relationship, which honestly felt like breaking through the surface and taking a deep breath after being underwater for so long. For the first time, I wasn't coloring my hair to mark change or chase excitement. I felt safe, grounded, and seen exactly as I was.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia
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2025: The Red Era

This year, I eased back into color with a reddish-brown dye—no bleach, just warmth. But after a few months, I found myself craving something bolder. I went fully red, and it was awesome. I'd say this was the era of freedom, but with security.

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Photo: Cheska Santiago, ILLUSTRATION: Kurt Villagracia

So that's my Hair Eras Tour: an eight-year rollercoaster of bleach, breakdowns, and (some) breakthroughs. Much like Taylor and her albums, each hair color marked a chapter—some loud, some tender, all honest. Every shade was a reminder that change can be both messy and magical. I learned that reinvention isn't necessarily about becoming someone new—it's about remembering who you were all along.

7 Things I Wish I Knew Before I Dyed My Hair In Crazy Colors

No regrets, though! ;)

READ HERE
Cheska Santiago

Cheska is Cosmo's Lifestyle Editor. She loves hoarding blushes, oversharing in drafts, and pretending impulse buys are "for work." Follow her on IG: @cheskasntg

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