My Most Embarrassing Fashion Phases, Ranked

It’s a little bit sad when you realize that you’ve outgrown experimental fashion phases. It’s like learning you may never get any taller, which I figured out in sixth grade. All those million alternate versions of you don’t feel tangible like they once did. The upside is that who you are settles even deeper into your DNA. Getting dressed is easier. You buy less. Your social media presence is more cohesive.

The past, meanwhile, waits to haunt you in the form of processed disposable Kodak camera photos hiding in your childhood bedroom. I recently discovered all of them during a trip home. Here are my eight worst phases, the ones I’m most embarrassed about, ranked from “meh” to “I don’t know her.”

8. Catwoman (22 to 24 years old)

What a blessed, brief time it was when I embraced an all-black wardrobe for the sake of my bank account and small closet space. The day I realized all-black meant no one could tell that I was re-wearing the same thing — especially at night, when I was “going out” often — was liberating. All I had to do to get ready was my hair and makeup. This was the sweet spot of early social media, when it wasn’t common practice yet to post every single photo to Yung Instagram each and every time my friends and I did anything. Things were stylistically simpler back then. This phase comes in at number eight because it wasn’t actually embarrassing; it’s retrospectively boring.

7. Before the Kardashians… (21 to 22 years old)

Let’s just admit that we’ve all made more than one post-grad social appearance in a bandage skirt. Let’s also admit (safe space) that every once in a while we look back on this short-lived “going-out phase” like…Did I look kind of amazing in that or what?

6. Too-Old Disney Channel Super Star (15 years old)

It didn’t matter if you were Team Lindsay Lohan or Hilary Duff (in the fight over Aaron Carter), you wore the same thing: a peasant skirt, a spaghetti-strap top and a denim jacket (in case it got chilly in my best friend’s converted-into-a-TV-room-basement). It was the ultimate outfit, my first foray into dressing like literally everyone else while feeling supremely independent. That’s probably because I was among the first to snag a pair of those two-dollar slippers from Chinatown.

Speaking of those slippers, how did all of us across America know to buy those shoes at the same time? They were the footwear equivalent of how every ’90s kid magically knew to blow into cartridges in the case of a Nintendo glitch.

5. “Punk Rocker” Without a License (13 years old)

Nothing said anarchy like asking my dad to drive me to the mall so that I could spend my babysitting money on an ironic Care Bears tee at Hot Topic. That’s why the Warped Tour was cool, because I could ditch my dad in the air conditioned Parents’ Tent.

Pants were utilitarian during this phase: a loop on the thigh for a hammer I’d never use, giant pockets, lots of grommets for bondage straps and chains. Every mother’s dream. Shirts were emblazoned with the logos of skate brands (I did not skate), band names (never to be worn to see said band, of course), screen-printed 1980s cartoon characters or all-black with something sarcastic in white writing, like “I see stupid people.” I stacked a million rubber bracelets up my arms from wrists to elbows but accessorized with one belt, and it was covered in pyramid studs. My black Misfits sweatshirt had holes in the sleeves for my thumbs to stick out of. Lyrics written in Wite-Out covered my backpack — this was just pre-AIM profile. Pink Rocket Dog sneakers completed the outfit, or Chuck Taylors. And I was punk, not goth, DAD.

4. Going-Out Top/Armpit Bag Cliché (19 to 20 years old)

This phase was some sort of ’90s carryover, I guess. It’s not so bad in that I get the appeal of wearing a cool top with jeans. I think it was the bootcut legs plus the pumps that went with, not to mention the bag that lived underneath my pit at all times, that brought this phase to number four on our list.

3. Peak Teen (16 to 17 years old)

Well before Instagram, the unofficial uniform of the 2005 “Cool” Teen meant layered polo shirts from Abercrombie with a denim skirt from American Eagle and a wide brown belt of unknown Western origin that would hang around one’s hips with zero intention of holding up her very low waistband. Bonus points if you wore kitten-heel flip flops. It was all very The OC. 

2. College Freshman Experimenting With Fashion (18 years old)

This was a style transition rather than a phase, but I didn’t totally know I was in style purgatory. I wasn’t that self-aware yet. The math looked something like leggings + Uggs + Juicy Hoodie, and then to really let everyone know I knew about fashion, an elastic headband around my head like a flapper. Oh yeah.

1. College Senior Experimenting With Fashion (21 years old)

Listen up world, my cupcake-puff of a skirt and white tank top with funky black shoes (I only owned black “going out” shoes at this point for some unknown reason, that and a metallic pair from prom) told anyone who glanced my way. Not only have I seen every episode ever of  Sex & the City, not only do I deeply identify with Carrie Bradshaw and especially her relationship with Big, MY pyramid belt — the one I have chosen to wear around my waist because it’s the ultimate juxtaposition considering the balletic nature of this outfit —  is from childhood. Besides, I went through a little bit of a punk phase when I was younger, so this is authentic.

Shout out in the comments if you went through any of these too. We’ll get through the embarrassment together.

Illustration by @CrayolaMode. 

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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