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:
Void of frills of fuss, this low-key design is one you can reach for year after year.
Honestly, these look more expensive than they actually are.
I can't see these staying in stock for long.
Style with a miniskirt or pair a floaty dress.
While I love these in the black, they also come in a supple suede style.
This elegant plum shade is set to be a key hue this autumn.
I always come back to Paris Texas for their chic footwear collection.
In my opinion, every great wardrobe starts with a pair of sleek, knee-high boots.
-
These $50 Old Navy Zipped Boots Are Just as Chic as the $1500 Pair I Have Been Coveting Since Last WinterThey're on sale for $30 right now.
-
Penny Loafers Are Fine, But Expert Dressers Know This Flat-Shoe Trend Makes for Elite-Level OutfitsEspecially with jeans and trousers.
-
Looking Chic in Cropped Jeans This Winter Means Wearing This Boot Style and ColorElizabeth Olsen would know.
-
You Have About 3 Weeks Left to Wear This Trending Outfit Combo Before Winter Dressing Fully Kicks InHere's the inspiration.
-
My Sister Asked Me What She Should Buy From Amazon—30 Fashionable Items I SuggestedBasically, everything on my Black Friday wish list.
-
Elizabeth Olsen's The Row Boots Are Chic, But These Ones Cost $1360 LessIt's girl math.
-
Only People Who "Get It" Are Wearing This Heeled-Shoe Color Trend Instead of Black or TanBella Hadid is one of them.
-
Here's Every Winter 2025 Trend Taylor and Gigi Just Wore With Their Chic Black Coats in NYCJust two best friends with the same taste in coats.
