Not to Upset You, But Ashley Tisdale's Cringey '00s Outfits Are Cool Again

It's time to apologize to 2021's most unexpected style icon.

Not to Upset You, But Ashley Tisdale's Cringey '00s Outfits Are Cool Again
Photo: Getty Images

If you're still of the mindset that fashion has rules that can't and should not be broken, it's time to have a talk. Leggings can pass as pants. Everyone can wear stripes. And, all those '00s trends that were once declared cringey and terrible just a few short years ago? Well, they've definitely made a comeback — so, grab your mid-section belt, ballet flats, and boot-cut jeans, and fully rethink what's "in" and "out."

Also, while we're at it, all of us should probably apologize to Ashley Tisdale. For over a decade, the actress and new mom has been the poster child for illogical, Disney-inspired outfits that we promised would never return. But, guess what? Against all odds, similar looks are popping up in 2021, and it goes well beyond Harry Style's Grammys boas.

If you're unwilling to accept it, that's fine. But, you might want to sit down before you scroll, because the proof is pretty shocking. The case for embracing throwback Tisdale style is strong, and it's probably only a matter of time before top models and influencers begin using these outfits as inspiration.

Denim Skirts, Long Socks, and UGG-like Boots

Ashley Tisdale
Mike FANOUS/Gamma-Rapho via Getty Images

Perhaps we wouldn't wear it all together, but then again, never say never. We fully accepted the 'ugly,' comfy shoe comeback months ago (along with Birkenstocks and Crocs), and still enjoy the preppy feel of a longer-length sock. Even denim skirts are suddenly being sold everywhere, just in time to take their rightful place as the ultimate summer staple.

Vests and Pleated Skirts

Ashley Tisdale
Jeffrey Mayer/WireImage

First of all, this Suite Life shot is iconic, and Tisdale's outfit — especially the plaid skirt — falls right in line with the viral schoolcore trend. Just swap out the long-sleeved tee for a sweatshirt and she's practically a Gen-Z, Instagram or TikTok influencer.

Dresses Over Pants and Ballet Flats

Ashley Tisdale
Mirek Towski/FilmMagic

We're sorry, but this combination is a thing again; we've spotted dresses over pants all over the spring and fall runways, and after a full year at home, simple, sweet flats have become the happy medium between comfortable and elevated footwear.

Mid-Section Belts and Monogrammed Bags

Ashley Tisdale
Kevin Winter/Getty Images

Sure, belting a T-shirt still seems a little random, but styling this accessory with a flowy dress is actually super flattering. Aside from cinching our waist with something statement-making, those monogrammed logo bags we loved back in the day have also resurfaced — and yes, that means itty bitty baguette versions, too.

Bold Leggings and Kitten Heels

Ashley Tisdale
John Sciulli/WireImage

Nothing against classic black leggings, but every time we see celebrities like Jennifer Lopez or Kaia Gerber wearing stretchy, colorful bottoms, we feel inspired to switch it up — just like Tisdale did with her white pair in 2006. Also worth pointing out? Her kitten heels, which have seemingly become summer 2021's new "It" shoe.

Cold-Shoulder Shirts and Butt Fashion

Ashley Tisdale
Michael Bezjian/WireImage

Before they were vaccine shirts, they were known as cold-shoulder 'going-out' tops, and yes, they paired perfectly with bedazzled butt jeans, which is another old trend that's on-the-rise.

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