I initially pitched this story as an anti-dresses over pants piece, paralysed with fear the look would take over again after seeing a few influencers flirting with the 2000s trend on Instagram.
I did not feel emotionally strong enough for this particular noughties resurgence.
But, in the time it took for this article to get commissioned and for me to procrastinate working on it before, eventually, beginning to research the 00s history of dresses over pants, I've seen the light.
We were wrong to mock Ashley Tisdale and everyone else who boldly donned a dress over a pant.
There, I said it.
To understand it, we have to think about why the dress over pant era happened
Fashion trends of the noughties were driven by rampant consumerism, thanks to an overwhelming obsession with celebrity culture and the rise of fast fashion.
Back then, Perez Hilton and TMZ were everything.
We lived at the mall, where we spent too much time trying on matching Juicy Couture sweatpant sets because Britney Spears and Paris Hilton were papped in them.
We layered T-shirts over long-sleeve tops not for warmth, but because that's what Hilary Duff and Miley Cyrus did on their respective Disney Channel shows.
We cinched our waists with chunky belts (even though our jeans were, tragically, low-rise), because the glossy celebrity magazines told us over-accessorising was a must.
This was a world that hadn't yet lived through the GFC, or followed live updates of Kim Kardashian's 2016 Paris robbery, or been slowly forced to come to terms with the environmental and social impacts of the fast fashion we were at that point only newly obsessed with.
We wanted everything our favourite celebrities had and our favourite celebrities were (for a brief moment in time!) dressing in clothes we knew where to buy and could actually afford — or at least afford to imitate.
We also wanted everyone to know we had all the things, and the best way to make that happen (for lack of social media) was to wear as much of it at once as possible, because that's what everyone who was anyone was doing.
The mood was "ludicrously capacious" bags.
In that sense, it makes perfect sense the dresses over pants combo had such a chokehold over us in the early 2000s.
Here's why it was (and is!) good, actually
I've spent years thinking of the layering technique as the worst sort of noughties garishness (and so, as it turns out, has Ashley Tisdale).
But now I see it as so much more.
Yes, it was a lot to take in. But that was the look's purpose: it was intended to be more interesting than conventionally beautiful.
And how insouciant a vibe is that? Especially in a red carpet setting, where every element of celebrities' looks are painstakingly analysed and the safe option (floor-length gown) would have been readily available to the ingenues of the day.
I'm sorry, but it was also super practical
Sometimes you just want to Wear The Damn Dress but it's too cold, and tights don't look right. Or you want to Wear The Damn Dress but wearing it on its own or with tights gives you gender or body feelings that aren't great.
In those instances, pairing a dress with a jean or a pant can help you feel good, while also making you look like that cool person who simply does not care about other people's opinions or breaking fashion "rules".
Because that cool person trusts in themselves to know what's good — regardless of whether that fits in with society's view — and they're unafraid to have fun and experiment with the clothes they wear.
Just look at the expression on Ashley Tisdale's face. She knew she was *that* girl even if no one else accepted it.
See also: wear pants under a dress and you become all, "Chafing who?" And who doesn't want to exist in a world without chafing?
See double also: there is a strong possibility that part of the reason the dress over pant combo gained as much strength as it did was because of the popularity of low-rise jeans at the time.
Ass crack on public display is never a good thing.
See triple also: could it have been a way for Disney Channel girlies to wear the uber short miniskirts that were popular at the time while remaining the modest tweenie bopper "role models" they were under immense pressure to be? This was also the era of the celebrity purity ring, after all.
Dress over pant never really stopped — but it looks and feels different these days
The wearing of a dress over a pant feels much more considered so far in this decade.
The combination has evolved with us, which is why it's an appealing option to the people who seek to experiment with the clothes they wear and dress for themselves — just as it was back then.
Rosetta Getty and Chopova Lowena are among some of the smaller (achingly cool) designers to have beautifully executed the early 2000s layering technique in recent collections, as have numerous larger houses. And I, of course, have to mention the 2022 Katie Holmes incident.
Off the runway and away from Hollywood, influencers are wearing the ever-divisive look well, too.
Try to tell me Masego Morgan doesn't look cute in her handmade crochet dress, worn over wide-hemmed utility vibes jeans.
That's what I thought.
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