Mid-2000s Movie Fashion: A Tragedy

Proof that we were all “seriously disturbed” when it came to clothing in the time of Paris and Lindsay.

To me, movies that I loved growing up as a pre-teen are still like candy. If I see Miss Congeniality on cable, I’m at least putting it on until the “self-defense talent” scene. While revisiting old favorites is usually an only minimally embarrassing pleasure, I find myself cringing at the outfits that I thought I LOVED during the initial watch. The fact of the matter is that the 2000s favored boot cut jeans, lacy camisoles, and trucker hats. It was trucker hats galore, you guys. Maybe one day, my children will ask me if I kept any of my American Eagle polo shirts, but for now, I am going to confess my horrible sins: my misguided self loved some seriously questionable fashion.

Here are just a few of the outfits that I thought were ~*~iconic~*~ and aspirational:

The outfit in Cady Heron’s daydream where she falls into the trash can at school.

Let me tell you something--Mean Girls holds up. It is a new classic for a reason, and I can still watch it and genuinely enjoy it, not just for the nostalgia factor. The only aspect of that movie that’s dated (other than the technology) is the fashion. The graphic tees and low cut jeans are such a relic of the time, and nothing says that more than the first time Cady (Lindsay Lohan) is seen as one of the Plastics. 

When I first saw this outfit, I was like, “Oh wow. YES. Fashion!” Cady was rocking pastel realness--not only did she have a flouncy patterned mini skirt, but her baby blue zip up hoodie made her look tooooootally ready for study hall. I thought it was so sad that this was the look where she accidentally fell into a trash can in the hallway. As I look back, I don’t think this look was “trash can worthy” necessarily, but Karen’s tank top that says “Bling Bling” in Gothic font really steals the show.

The first time Andy impressed Miranda Priestly. 

Okay, so if you haven’t seen The Devil Wears Prada, it’s a must. This is one of Meryl Streep’s most awesome, quoteworthy performances, and it has both Stanley Tucci AND Emily Blunt! Basically, Andy (Anne Hathaway) wants to be a serious journalist, but isn’t able to get a job in the newsrooms she wants. She does, however, land a position as an assistant to the very scary fashion editor Miranda Priestly. She doesn’t fit in, and decides that a makeover will help her make it in this industry. 

The outfit I’m talking about, unfortunately, is the AFTER outfit. I don’t think it’s necessarily HORRIBLE, but I honestly thought that the mini skirt and black school-girl blazer was ON POINT back in the day. The girl is wearing seven gold necklaces and bangs. What else do you want? Even though this movie was made in 2006 (PRIME JUICY SWEATPANTS TIME) the fashion in this movie about fashion is mercifully not terrible. I just am a little embarrassed that I loved this outfit.

Sharpay’s blazer that gets nacho-ed in the cafeteria.

THIS is the outfit that makes me hang my head in shame, okay? First of all, I caught High School Musical on Disney Channel a few months ago, and there were way too many high school girls wearing blazers at that school. I’m not joking or exaggerating when I tell you that there was not a school day that went by where someone was not wearing a Sag Harbor structured jacket. It is just...masterful in how wrong it is when it comes to a teenage girl’s wardrobe. Truly masterful.

What’s even more amazing is that I was totally in on the business casual fantasy. Sharpay’s outfit during the song “Stick to the Status Quo” was my absolute favorite. Yes, we have the white boot cut pants. You better believe that this salmon-hued floral blazer was accompanied by a thin robin’s egg blue belt and the haircut of a woman who doesn’t know WHY she isn’t allowed to combine coupons. Why did I think this made sense for someone who was literally my age when I watched this movie? I was devastated when that blazer was accidentally covered in nachos at the end of the song. I feel like the ruining of all of my favorite movie outfits was a bit of a sign...

Don’t get me wrong. There are some amazing outfits that will forever be in my Fashion Hall of Fame (Jenna Rink’s “Thriller” dress! Elle Woods’ Bedazzled Bikini!), but when it comes down to it, this article is the only place where I will admit that I loved mid-2000s movie fashion. 

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