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‘Pen15’ Is Bringing Back Cringeworthy Middle School Fashion From the Year 2000 — Why You Have to Watch

I thought the embarrassing middle school years were behind me, but nope. After watching one episode of Hulu’s “Pen15” I was transported back to the year 2000, all thanks to the wonderfully hideous fashion and superb portrayals of 13 year olds.

If you haven’t watched the comedy series, which debuted Season 2 in September, it follows stars and creators, Anna Konkle and Maya Erskine, as they play versions of themselves as teenage outcasts, surrounded by actual teenagers.

It’s set in 2000 and follows them in sixth and seventh grade as they navigate puberty, friendship, and of course, style. Their unfortunate haircuts, immature banter and rolly backpacks will make you facepalm episode after episode as it takes you back to those eerily similar awkward years.

The first challenge when it came to dressing the actors for this time period was to make 30-somethings look 13.

PEN15 -- "First Day" - Episode 101 - It’s the first day of seventh grade in the year 2000. School rejects, Anna and Maya, get a lot of unexpected attention. Dustin (Isaac Edwards), Brandt (Jonah Beres), Alex (Lincoln Jolly), Sam (Taj Cross), Maya Ishii-Peters (Maya Erskine), and Anna Kone (Anna Konkle), shown. (Photo by: Alex Lombardi/Hulu)
Maya Ishii-Peters (Maya Erskine) and Anna Kone (Anna Konkle) were dressed in low-rise flare jeans and cargo shorts that helped hide their adult curves.
CREDIT: Alex Lombardi/Hulu

“We had to figure out a way to make Anna and Maya look flat-chested again,” costume designer Melissa Walker told FN. “We created several different versions of compression bras so that they could wear them under different shirts and not have anything seen.”

Staying true to the period was key for Walker, who sourced from eBay, Goodwill, Etsy and other vintage shops.

“We really had to work very hard with the clearance team because I think that if it was all done generic, it wouldn’t have had the trigger finger on those specific recollections and emotions,” she explained.

Think Etnies skateboard sneakers, puka shell necklaces, Gushers, Mudd Jeans, Tommy Hilfiger, AIM. Getting as specific as possible with popular labels from that time is the reason why the show is as cringe-worthy as it is — in the best way possible.

PEN15 -- "Posh" - Episode 106 - Maya gets a questionable nickname during a school project. Anna goes along with it, resulting in a test of their friendship and identities. Anna (Anna Konkle), Ian (Ivan Mallon), Margot (Annabelle Kavanagh), Brandt (Jonah Beres), Ben (Brekkan Spens), and Maya (Maya Erskine), shown. (Photo by: Alex Lombardi/Hulu)
Anna (Anna Konkle), Ian (Ivan Mallon), Margot (Annabelle Kavanagh), Brandt (Jonah Beres), Ben (Brekkan Spens), and Maya (Maya Erskine), shown in “Pen15” episode 106.
CREDIT: Hulu

For lead characters, Maya (Erskine) and Anna (Konkle), the trendiest of clothes from the Millennium were not in their closets, which differentiated them from the cool girls.

“Their clothes would just be a little out of style or a hand-me-down or something that’s not quite on the mark or the cool trend,” explained Walker. “Those cool trends would go to the popular girls and then when Maya and Anna start getting really into brands, they don’t execute it correctly. It’s about still having a sense of style, which they haven’t quite developed yet.”

More go-to shoe brands included Skechers, Adidas, Rocket Dog and Sanuk, which really brought the nostalgia home. You’ll see Anna in a pair of slip-on Adidas and Maya in metallic blue Superstars.

Walker said she worked closely with Skechers for Season 2 as the company re-created an iconic pair from the early-2000s, as well as Lucky brand, who reprinted 1999 and 2000 graphics on T-shirts for the show.

Pen15 costumes
Maya Ishii-Peters (Maya Erskine seen in Skechers sneakers in Season 2.
CREDIT: Hulu

To find inspiration, Walker, Erskine and Konkle looked back at their year books, old teen magazines and photos from their younger years. The costumer then essentially made closets for each character.

For instance, Alex (played by 15-year-old Lincoln Jolly), had all kinds of light blue and light green and yellow button down short-sleeved surf shirts, as well as Hurly and Quicksilver products. Brandt (played by Jonah Beres), meanwhile, wore skateboard-wear from Alien Workshop.

“We’re not ‘Sex in the City.’ We don’t need to show different trends. And though there was such a showcase on the costumes on this show, it was always to be in a realm of reality,” said Walker.  “It wasn’t to be high fashion or to be marketing some new trends. It was about staying true to what these middle schoolers would have been experiencing.”

She added, “I didn’t want the costumes to overshadow anything. I didn’t want to draw attention to it. I wanted it to just feel natural and be able to live within the story.”

If there’s anything you must do over the holidays it’s to binge-watch “Pen15.”

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