Some trends age like a fine wine and some, well, don’t. As fun as it is to play around with of-the-moment looks, sometimes practicality calls for investing in timeless pieces that will stand the test of time. As you might have guessed, this story is dedicated to the shoe styles that fit in this category.
I know what you’re thinking: It’s still scorching hot out, how can I think about fall boots? But it never hurts to plan ahead and take advantage of brand new arrivals while stock is still full of sizes. Inspired by the coolest women in New York, Paris, and more, scroll down to shop the 5 classic shoes you’ll love for fall.
1. Chelsea Boots
(Image credit: @himichelleli)
Dr. Martens
2976 Ys Chelsea Boots
These comfortable boots have a thick sole that's perfect for inclement weather.
Sam Edelman
Justina Chelsea Boots
Lug soles are so practical.
(Image credit: @chrissyford)
Marc Fisher Ltd
Yale Chelsea Boots
You simply can't go wrong with pointed black ankle boots.
Hunter Boots
Original Refined Chelsea Boots
These waterproof boots are perfect for rainy weather.
2. Knee-High Boots
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Loeffler Randall
Gia Tall Boots
Paired with a mini skirt, these boots are very Margot Robbie in Once Upon a Time in Hollywood.
Sam Edelman
Penny Boots
Take note: Riding boots are back in style.
By Far
Stevie Suede Knee Boots
By Far has done it again.
Aquatalia
Fabrianna Water Resistant Boot
They're chic and they're water-resistant. Win-win.
3. Ballet Flats
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Schutz
Arissa Flats
Square-toe ballet flats are very in right now.
Aeydē
Moa Leather Point-Toe Flats
A modern interpretation of the trend.
ASOS
Layer Leather Bow Ballet Flats in Black
This fantastic price is seriously tempting me.
Who What Wear
Cara Flats
Part ballet flats, part mules, 100% chic.
Mansur Gavriel
Dream Ballerina Flats
You can always count on Mansur Gavriel for high quality pieces that will last.
ASOS
Late Mary Jane Ballet Flats in Black
I'd wear these with everything from jeans to floaty dresses.
Loeffler Randall
Georgie Ballet Flats
So delicate. So beautiful.
4. Loafers
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Mansur Gavriel
Classic Loafers
Yep, I'd also wear these with high socks just like the outfit above.
Porte & Paire
Croc-Effect Leather Loafers
Yes, I want to channel my inner Rory Gilmore and wear these with a pleated skirt.
Tod's
Gommino Leather Loafers
These Tod's loafers are the definition of classic.
Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.