The Most Cringeworthy Things I Wore in 2008

Grab your digital camera, North Face jacket, and boots with the fur! Let's travel back in time 17 years to 2008.

May 15, 2025

Welcome to Forever Millennials, a place where I write about life, motherhood, getting older, stuff I love, and millennial nostalgia. Come for the laughs, stay for existential dread! XOXO.

It’s been a while since my last ~millennial fashion history~ post, but she is back!!! This time, we’re traveling back 17 years to 2008. (17 years AHHHHHHHHHHH)

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When I think of 2008, I can hear the faint cry of Low by Flo-Rida playing in the distance. Or is it LIVE YOUR LIFE by T.I. featuring Rihanna? Or is it LOLLIPOP by Lil Wayne? Or is it LOVE IN THIS CLUB by Usher? Or is it SEXY CAN I by Ray J? Or is it A MILLI A MILLI A MILLI A MILLI A MILLI A MILLI—

As long as it’s not I Kissed a Girl by Katy Perry.

2008 was a great year for music. I know everyone says that about their younger years, but I compared the Billboard Hot 100 Singles from 2008 to the years surrounding it, and 2008 had the most bangers that don’t now make me question if something was wrong with my hearing.

Like how was Crank Dat Soulja Boy a number one hit for multiple weeks in 2007? And how was Boom Boom Pow the top song of 2009????????? You can really tell the kids aren’t drinking as much anymore just by looking at the music charts. Millennials were always fucked up back then, and it shows.

2008 was also a peak year for Forever 21. And strapless tops. And color block dresses. And capri leggings not for working out, but for going out. All worn with light cardigans, North Face jackets, and Uggs. Or flip flops during summer. We woke up every day thinking, “I want to make my adult self cringe looking back on whatever I end up wearing today,” and we did just that.

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Below you will find the cringiest outfits (mostly from Forever 21) that I wore in 2008, which is all of them. Or at least all of the outfits I could find myself wearing in pictures online. This selection is limited now because everyone (myself included) made all of their Facebook photos private OR deleted them completely.

LET’S HEAD BACK.

The year is 2008…

Estimated Comeback: 2030 (or sooner at this rate)
Age My Daughter Will Be: 8
Ages I Was: 19 & 20
College Year: Sophomore Spring & Junior Fall

First up, we have 4 outfits that capture the fashion of the time, which was Forever 21 chic:

This is what I picture when someone says 2008. Me in a cheap little Forever 21 top, occasionally with spaghetti straps, but most likely strapless. My thoughts on each outfit from left to right:

Photo 1 - Ugly patterns: There was nothing I loved more in 2008 than going into Forever 21 and finding a top with a pattern. It’s how we showed our personalities. What personality was I trying to show with this? I have no idea. This top features the millennial pink and brown color combo that had a HOLD on every 20-something’s home decor in the mid-2010s. But the top on my skin? No. It’s literally the same color. These chaotic patterns are why millennials now only wear beige, black, and white with occasional appearances by brown and navy. Millennials be course correcting like no other.
Photos 1, 3, and 4 - Silver jewelry: I used to wear the biggest fake diamond stud earrings that I could find every second of every day in 2008. I also used to wear that silver Tiffany’s heart necklace every day until I left it inside of a treadmill’s cupholder at the Ithaca College gym before heading home for winter break. RIP.
Photo 2 - An introduction to big gold jewelry: About halfway through 2008, gold jewelry emerged and we entered our chaotic jewelry era. The necklaces had way too much going on and the earrings were cheap, heavy, and full of infections. I literally got so used to my earring holes crusting over, I think I thought it was normal??????? In this pictured outfit, I wore a big gold necklace and big gold earrings together. This was a choice.
Photo 3 - Strapless tops and tan lines: I think the majority of my wardrobe in 2008 was strapless tops and dresses, and of course I had to pair them with ~tan lines~.
Photo 4 - Color blocking tops: I remember buying this top. It was from Forever 21, and I felt like I had scored the deal of the century because I didn’t think it looked like it was from Forever 21. It absolutely did, but delusional 19-year-old me didn’t have a clue.
ALL photos - Long side bangs: The side part was living its best life in 2008 thanks to our long side bangs. They weren’t traditional side bangs because they were so long, but they were more of an excuse to style our hair in a very unnatural way.

Now, my worst outfits from 2008 (from pictures still online—there could be worse ones out there!):

Oh no. From left to right:

Photo 1 - The brown and black combo: WHY DID WE DO THIS? The brown was too light and the top was covered in GEMS. And then I paired it with the lightest cardigan that wasn’t there to keep me warm, so like what was its purpose? FASHION? WAS THIS FOR FASHION?
Photo 2 - The black turtleneck t-shirt sweater: I wore this all the time. I think we all did? It was one of our uniforms. I got it at the end of 2008, so it was also a 2009 thing. There’s also a chaos necklace, which we talked about before.
Photo 3 - A horrendous sweetheart neckline strapless top: Who saw me put this on and told me I looked good? JAIL CALLED, IT SAID WTF. This didn’t fit my boobs. And the brown and red colors? And the pattern? And what are those dangly ball earrings? Everything in this photo was a choice.
Photo 4 - Outfits ruined with zip-up sweatshirts and flip flops: This is the same pink strapless top pictured in the first batch of photos, but the outfit was different. This outfit looks like I was drinking at a high school party in the woods, but no. I wore the zip-up Abercrombie (or Hollister) sweatshirt and flip flops OUT to a party in Boston as a college student. Both AS PART OF the outfit. WHAT THE FUCK. Those flip flops were from J. Crew and weren’t plastic, like Old Navy ones, so I think I deemed them appropriate going out shoes. Not to mention, the shirt is falling down and looks extremely unflattering! The CHOICES! The HORROR!

Okay and my two most 2008 outfits that are both cringey and classic lol:

Photo 1 - The most cliche 2008 outfit you’ve ever seen: This outfit has everything. Boyfriend jeans, salt-stained Uggs, a Coach wristlet, the color brown. Those jeans were 100% from American Eagle, and I can feel the crunchy ripped bottoms just from looking at this photo. Unlike everything else, this top was NOT Forever 21. I forget where I found it, but it was either Arden B (LOLLLLLL) or Cache. It had a very low cut v-neck and a brown woven belt, and I have no idea why I remember this. The coke bottle is full of Captain Morgan’s rum and diet pepsi, two things I haven’t looked at since 2010. And THE BASEMENT, which truly could have been at any house party in Ithaca because they all looked like this. I think all houses in all college towns had basements that looked like this tbh.
Photo 2 - Capri leggings and THE color block dress. I say dress, but was it a dress?????? It was so short. AND ON THE TOPIC OF “SHORT,” WHAT THE FUCK IS WITH THE LEGGINGS???? They aren’t just cropped, but they hit right below the knee. Like these aren’t even capris. They are shorter than capris. And I’m short! Why were we wearing these???? And why did everyone have that Forever 21 dress? And why did it work better as a beach cover up in the years after 2008? Also, shout out to chaos necklace.

Alcohol was part of our outfits in 2008, too.

The cringe. THE CRINGE. Kids today would never. High schoolers would never.

Photo 1 - Beer: I don’t think I’ve had beer since 2011.
Photo 2 - Captain Morgan: Definitely haven’t touched Captain Morgan or rum since 2010. Also, unrelated, but the shirt I’m wearing in this photo is Free People!!!! I don’t know why I remember that, but it was from Nordstrom. Not Forever 21!
Photo 3 - Andre champagne lol: Do they even still make this????????? Remember it was like $3?!?!?! I get indigestion by just thinking about it.