Sorry, Jenna, But I Would Never Wear Knee-High Boots to the Airport

Jenna Ortega walks through the airport wearing a black leather jacket with blue denim shorts and black knee-high boots.

(Image credit: Splash by Shutterstock)

published 18 August 2025

The last time I was at the airport, my trip through security swallowed up a full 30 minutes—not to mention a fair amount of unplanned stress. Compared to previous dashes, when I’ve glided through in five minutes or less, this was one of those high-stakes situations that makes you vow you’ll arrive extra early next time. So, newly determined to keep my journeys as seamless as possible, you can imagine my reaction when I spotted Jenna Ortega wearing the one shoe trend I’d never risk at security.

Chic as she looked, Ortega’s choice of knee-high boots immediately went on my personal no-fly list. The thought of fumbling with zips, tugging them off under pressure in the security line and padding barefoot through the scanner is enough to put me off for good. I’ll stick with fuss-free slip-ons—like sleek leather loafers or easy trainers—that make the whole process a breeze.

That said, Ortega’s outfit itself deserves a moment of appreciation. Teaming a rich chocolate-brown funnel-neck jacket with cut-off denim shorts and dark sunglasses, her look made up for in chicness what it may have lacked in practicality. And while I love the look of shorts paired with knee-high boots (it’s one of my favourite pre-autumn outfit combinations), I’d personally reserve it for a weekend outing or a casual afternoon rather than a security line.

Still, inspiration is inspiration—and Ortega’s ensemble has me eyeing up the season’s best knee-high boots. Read on for the chicest pairs worth shopping this autumn.

Shop Knee-High Boots:

H&M

Knee-High Boots

Void of frills of fuss, this low-key design is one you can reach for year after year.

H&M

Knee-High Boots

Honestly, these look more expensive than they actually are.

Zara

Leather Knee-High Boots

I can't see these staying in stock for long.

Whistles

Black Matteo Knee High Biker Boot

Style with a miniskirt or pair a floaty dress.

Asos

Conan Pull on Chunky Boots

While I love these in the black, they also come in a supple suede style.

Le Monde Beryl

Allegra Leather Knee Boots

This elegant plum shade is set to be a key hue this autumn.

Paris Texas

Jane Leather Knee Boots

I always come back to Paris Texas for their chic footwear collection.

Staud

Wally Leather Knee Boots

In my opinion, every great wardrobe starts with a pair of sleek, knee-high boots.

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Natalie Munro is Who What Wear UK’s news writer and has worked in the fashion industry since she graduated with a degree in Journalism from the University of the Arts London. Natalie’s experience in the industry spans journalistic and styling roles that have seen her work for publications including British Vogue, Conde Nast Traveller, Vogue Ukraine, AnOther Magazine and Elle UK.

With an interest in uncovering the latest fashion trends, Natalie takes a leading role in identifying news for Who What Wear UK. Reporting on a daily basis, Natalie focuses on trends on and off the runway, as well as street style and celebrity fashion. Natalie also creates content for Who What Wear’s social channels including TikTok and Instagram on a weekly basis.