Winnipeg Free Press (Newspaper) - August 19, 2025, Winnipeg, Manitoba
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TUESDAY, AUGUST 19, 2025
Millennials’ high school clothes are cool again
FASHION-GO-ROUND
P
HILADELPHIA, Pa. — The secret
to time travel is the camisole.
Enter the portal — an Old Navy
dressing room in suburban Philadel-
phia — put one on, and if you are a
millennial of a certain age, you’ll be
transported 20 years into the past.
The King of Prussia Mall is, mirac-
ulously, just as we left it in the early
aughts: the jeans are boot cut, baggy
or wide legged. The scent of Auntie
Anne’s pretzels permeates the air. The
skirts have a bubble hem or a raw den-
im edge or a tiered, white prairie cut.
The sound system is playing Cold-
play and Avril Lavigne, and Freaky
Friday is back in theatres. The tops are
halters and tubes, and most impor-
tantly, the camisoles have a contrast
lace trim. Layer as many as you can
for maximum style, just like we did in
high school.
And, just as in high school, we are
back in a mall dressing room trying
on tops, which look like the very same
tops we wore in high school 20-some-
thing years ago because fashion and
time are a flat circle, and we mil-
lennials have aged into our second
go-round.
We recall when it happened to our
mothers, when we begged for flare
jeans, circa 1999.
“Bell bottoms, really?” they said,
with a bit of disdainful amusement.
“That’s the stuff we used to wear in
high school.”
Mommmmm. You don’t understand.
But we do now, kind of: the genera-
tions after us have been looking to the
1990s and 2000s for fashion inspira-
tion. The difference is that it’s being
marketed to us, too.
Abercrombie has ditched the soft-
core marketing and logo tees in favour
of elevated basics that college girlies
and mid-career girlbosses alike are
snapping up.
Same for Gap and Old Navy, with
Zac Posen at the helm. Stores that
didn’t exist in the United States when
millennials were in high school, such
as Aritzia and Princess Polly, are
copping styles from Delia*s (RIP) and
Charlotte Russe.
We put on the camisoles and the
cropped, baggy jeans with flip flops,
and examine our reflections in the
sparse, white, cement-floored dressing
room. We come out, look each other
over and double over laughing. We are
14 all over again.
But a question is gnawing at us: what
sort of midlife crisis might we trigger
when we try on the clothes of our
carefree youth, but now with mort-
gages and silvering hair and our first
mammograms looming?
As it turns out, the golden age of
mall culture that we remember so
fondly was more like its grand finale.
New malls had cropped up in the
United States every single year for the
second half of the 20th century — and
then in 2007, amid a nascent recession,
none. By 2008, Newsweek was asking:
Is the American shopping mall dead?
What was left of brick-and-mortar
shopping got further decimated in
2020. But then, right on schedule, just
as the 20-year nostalgia cycle would
have predicted, a newly consum-
er-aged gen Z started yearning for our
mall-sourced 2000s styles: the Hen-
leys, the light-wash denim, the rugby
shirts, the Juicy Couture sweatsuits
and the Oakley sunglasses.
And shopping at the mall, they quick-
ly learned, got them to you even faster
than the next-day delivery option
online.
Many of the original purveyors of
these styles have lived to sell them
again, some in part because they
shrewdly expanded to win back millen-
nial consumers as they aged into their
adulthoods and careers.
And thus, here we find ourselves
in 2025. In a timeline where teens in
baggy cargo shorts are idling away
their summer weekdays in the frosty
industrial AC of the mall again, dous-
ing themselves with testers of Aber-
crombie & Fitch Woods cologne. Unlike
us, many of them roam around with
devices that tattle their exact locations
to their parents.
Still, here they are, retracing our
steps on the hunt for what we bought in
the same place at the same age.
Do you remember when we were
teenagers, and we’d buy a hoodie or
a T-shirt with numerals of a random
“vintage” year on it to look cool? Well,
we have some bad news for you. In
Hollister, the year emblazoned across
the hoodies is … 2001.
The “2000s Vault” collection, re-
leased this summer, features the same
tiered ruffle skirts, lace-trim babydoll
tops and tight cable-knit sweaters that
we totally wore to that party in Zack’s
parents’ basement after the football
playoffs. It’s a bit of a mind warp to put
them back on.
This looks cute, our brains say, but
maybe it’s because they have teleport-
ed us back to that party, but suddenly
the reverie gets interrupted when our
adult bodies release a glissando of
clicks and creaks as we wriggle out of
said ruffle skirts.
It’s the same over at the Gap, when
we put on capri pants — they still
make us look short, we’re sorry to re-
port — and a tube top. The AOL dial-up
sound. The cheerleading squad. The
halter tops and lettuce-hem dress-
es at Urban Outfitters. A JanSport
backpack. The homecoming dance.
The Henley cap sleeve T-shirt layered
with a chunky belt from Lucky Brand
Jeans. That first breakup. Your messy
locker. The senior boys.
In American Eagle, flipping through
a pile of contrast-denim wide leg jeans
— this was before the Sydney Sweeney
ads earned internet scorn and a nod of
approval from U.S. President Donald
Trump — we discover that jeans now
come in a triple zero, and gasp. We
remember when the double zero was
invented: 2006. A few of our old insecu-
rities are reignited. Hollister, despite
carrying larger sizes, doesn’t always
have them in stock for the things we
want to try. The dressing room lighting
is unflattering and sallow. The Aber-
crombie is closed for renovations.
Throughout it all, we’re surrounded
by teenage girls who are just like the
teenage girls we used to be.
In some ways, the younger gener-
ation is wearing these trends better
than we did. We remember our sub-
urban high schools to be oppressively
conformist — so many students wear-
ing the same Abercrombie polo shirts;
the same low-rise, boot-cut American
Eagle jeans; coveting the same logo
Coach and Burberry bags; the same
Uggs; the same, the same, the same.
From our 25-years-older perch, it
seems like teens today are more ex-
pressive and creative dressers.
A few of our teenage staples have
gotten chic upgrades, too. We admired
a denim bubble-hem dress at Ameri-
can Eagle with a basque waist — a far
more interesting cut than the babydoll
shape it would have taken in our day.
And knit tops have shortened and wid-
ened to something more recognizably
human-shaped, thank God.
The yin-yang earrings we saw at
Lucky Brand? Well, those probably
could have stayed in the previous mil-
lennium. Same for all things low-rise,
especially low enough for a thong to
peek out, or putting words across our
butts on sweatpants. It made us wist-
fully nostalgic for a simpler time, but
was not an outfit we’d choose to repeat.
But capri pants? Bubble hems? Prai-
rie skirts and rugby shirts? We greeted
them again like old friends. Friend-
ships evolve over decades, though, and
sometimes they no longer fit. To be
40 going on 14 is to be haunted by the
question: can we pull these outfits off?
The answer, respectfully, is: Who
gives an F. Approaching middle age
dramatically — blessedly — reduces
the amount of time one spends caring
about what other people think. We only
wish we hadn’t wasted so much time on
it before.
Because here’s what happens when
you look at yourself in a mirror at 40,
wearing the clothes you wore at 14: you
see two selves staring back at you. Of
course, you see the silver-haired ver-
sion who has gone up a few sizes, who
worries less about what the popular
girls and the cute boys will think. But
you also see that 14-year-old-girl, and
love that girl, and want to reassure her:
It all turns out mostly OK. Go ahead,
buy the miniskirt.
— The Washington Post
MAURA JUDKIS
AND ASHLEY FETTERS MALOY
ALLIE CAREN / THE WASHINGTON POST
Baggy is back, as this Levi’s store window asserts, but only on the bottom. On top, we’ve returned to skintight baby tees and camisoles.
People of all sizes look for more teenie-weenie in bikinis
DID bikini bottoms get smaller this
summer? The short answer? Yes. (Get
it? “Short”?)
You may have noticed it on swim-
wear-heavy TV such as Bachelor in
Paradise and Love Island, where the
cheekies got cheekier and the number
of thongs crept up. (Get it? “Crept up”?)
Searches for Love Island bikini on
Google spiked in July. And on beaches
and at pools, smaller bottoms have
spilled out into the general population.
(Get it? “Spilled out?” I’ll stop.)
Thongs are, perhaps unsurprisingly,
not for everyone, but some swimwear
designers report that there are custom-
ers who will wear nothing else.
When Hayley Segar launched One-
with swimwear in 2021, she offered
classic medium-coverage bikini
bottoms. After her designs began to
circulate on social media, she heard
from customers who wanted more
teenie-weenie in their bikini.
“The only comment we got was,
‘Thongs, thongs, thongs, thongs, where
are your thongs?’” Segar said.
By 2023, Segar realized that she had
to act fast to meet demand. She hastily
modified an existing full-coverage
bottom and rushed it to the factory.
“I literally told my technical design-
er ‘Just chop off the cheeks,’” she said.
That design, called the Huntington,
has remained one of her best sellers.
“Full coverage is dying,” said
Elizabeth Claire Taylor, CEO of the
plus size swimwear company Curvy
Beach. When she founded the company
in 2017, she never planned on offering
thongs. Her customers gravitated
toward high-waisted bottoms with full
posterior coverage.
But two years ago, she introduced a
cheeky cut. It was a hit. In February,
the company debuted its first thong. It
sold out.
Taylor has many customers who will
never even consider wearing a thong.
“When you go from booty-covered to
thong, you encounter things like butt
acne. You are entering into a vulnera-
ble territory, and I think you’re either
open to it or you’re not,” Taylor said.
She’s encouraged by the increased
demand for a variety of sizes.
“To me, in the current political
climate of this country, it is a way of
practising body autonomy,” she said.
Isabelle McKay, the founder of the
swimwear brand Isabelle Meira, doesn’t
sell thongs but has noticed a significant
uptick in demand for more-revealing
higher-waisted cheeky bottoms.
“Five years ago we’d sell probably
70 per cent full-coverage. Now I’d say
we probably sell 70 per cent cheeky,”
she said.
McKay sees a connection between
wider demand for clothes inspired by
the ’80s and ’90s, when higher waists
and narrower cuts were in vogue. That
could also explain that while bikini bot-
toms have shrunk, more modest tankini
tops are also having a major moment.
It may seem counterintuitive, but
some women have found that less cov-
erage can be more flattering.
“Higher on the hip, it just makes
more of a curve, it makes the legs look
a lot longer and slimmer. It’s about
creating optical illusions rather than
covering more,” said McKay. “Some-
times covering more can almost look
less flattering because it’s actually just
a bigger expanse of fabric.”
Javiera Del Pozo, a model from Los
Angeles, has been creating “haul”
videos in which she tries on swimsuits
since 2016. For years, she’s been wear-
ing her bikini bottoms backward as a
workaround.
“The front part will be smaller than
the back, so I’ll get more coverage
in the front and less coverage in the
back,” Del Pozo said.
But this summer, she’s been able to
find more suits that fit the way she likes.
“One, I want a good tan. I also want
to feel comfortable. If anything, cover-
ing up makes me feel less confident,”
she said.
Heather Short, who earns money
posting about plus-size fashion on
her thicknstrong33 TikTok channel,
agreed.
“For me, I’m just more comfortable
when things are cheeky and small-
er because I just feel it shows more
curves in my body. You always look
bigger when you wear bigger clothing,
in my opinion,” she said.
Sarah Chiwaya, a contributing editor
at Refinery29 and a plus-size fashion
expert, rejects “looking smaller” as a
goal. But she’s happy to see that more
revealing bottoms are increasingly
available for more consumers.
“I’m really excited to hear that
there’s actually been a trend of
things getting skimpier because it’s a
pushback against conservative culture
that’s been seeping into fashion.
There’s been a push to dress in a way
that is traditionally flattering, which
is very much a patriarchal concept
about covering up what’s improper and
impure,” she said.
Indeed, online summer discourse
has been roaring with arguments
about “trad” femininity and the politi-
cal implications of cleavage, long hair,
“good jeans” and heavy makeup.
In one sense, women deciding to re-
veal more of their bodies runs counter
to conservative notions of modesty.
On the other hand, if your concept of
“trad” femininity includes the tradi-
tion of courting men’s attention, then
showing more skin could certainly fit
that definition.
Depending on where you’re sunbath-
ing, skimpy swimsuits are nothing
new. There are beaches in Brazil or
Miami where thongs have been com-
mon for decades.
Of course, not everyone is happy
with a less-is-more approach to swim
bottoms. Destiny Mellow, a health-care
professional from Bay Springs, Miss.,
posted a now-deleted video with the
title “Confirmed: the cheeky bikini life
just isn’t for me.”
The video stemmed from her
frustrations while trying to find a new
swimsuit for a beach vacation.
“If I were to try and swim and
actually enjoy my vacation in one of
those bottoms I would quite literally be
flashing everyone at the pool or on the
beach,” Mellow wrote in an email.
But the less-skimpy items she found
in stores felt dowdy and outdated,
so she’s sticking with the suits she
already had in her closet.
“The whole section that offered what
I’d call decent coverage was giving,
‘Water aerobics at 5, bingo at 6.’”
— The Washington Post
SHANE O’NEILL
CURVY BEACH
ONEWITH
The plus-size brand Curvy Beach (top) has
had luck with offering smaller cuts to cus-
tomers of all sizes, while Onewith customers
wanted cheekier swimwear.
ARTS ● LIFE I FASHION
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