The Latest It Boot Trend Will Probably Lose You a Few Friends

A visit from Storm Emma during the Milan and Paris legs of show season proved to be a minor fashion emergency for the assembled editors. Instagram posts along the lines of, “Guess who didn’t bring flats or socks, but managed to pack the peep-toes?” started falling like snowflakes, and the street style photos had a distinctly dreary feel with all the grey slush in the background.

Not everyone came unprepared, however. Hey Woman founder Veronika Heilbrunner packed a pair of Italian leather lace-up boots by Diemme, styling them with elevated walking gear in the form of a cloud-like pink duvet coat and an orange Acne Studios beanie. But she wasn’t the only one who looked set for a summit climb up Ben Nevis.

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Blogger Aimee Song traded in her Roger Vivier mules for a stomping pair of hiking boots to attend the Dior show. Instagram’s Eva Chen picked a classic pair of Dr. Martens to brave the sludgy pavements. Supermodel Gigi Hadid (back in New York after the Paris shows) was still wearing weatherproof boots. Is it possible that Duke of Edinburgh–worthy hiking boots might be the new cowboy boots?

The boots have certainly gained traction in the past few months. There’s the Off-White collaboration with Timberland, which spawned a pair of gorgeously stompy velvet boots, and then the fact that cool-girl brands like Ganni have brought the kind of boots you might save for snow days into the mainstream. (The brand’s Masha Lace-Up Boots have been the It pair of the season and offer a cosy wool lining and track sole for a no-slip grip.)

Heilbrunner is certainly a hiking-boot enthusiast. Her favourites are by Acne Studios. “I have three pairs in different colours and keep adding new ones. They’re chunky, have a great rubber sole, are very warm and super comfy,” she says. She also loves the Roccia Boots by Diemme and, of course, Timberlands.

But Heilbrunner doesn’t save them for days with severe weather warnings only—she wears them year-round with everything from jeans and corduroys to floral dresses. “They literally work with anything, but I do love them most with a romantic Erdem dress or something disco from Christopher Kane. It’s all about the contrast,” she says.

But don’t panic if you don’t feel comfortable with wearing your ballgown with hiking boots. Here are eight ways to wear chunky boots in real life—whether it’s blizzarding or sunny outside.

1. Opt for Earth Tones 

Timberlands are the kind of shoes you either love or hate. Emili Sindlev just might change your mind if you’re in the latter camp. Pair these classic brown boots with other neutrals (a Burberry checked jacket and khaki track pants from By Malene Birger, for example) when the weather is slippery.

If Sindlev’s style hasn’t convinced you, maybe the Nellie Chukka boots will. The shoes have all the hallmarks of classic Timberland boots—caramel brown colouring, yellow laces, a rubber sole—but offer a slightly more delicate leather cushion around the ankle.

2. Find the Right Length Jeans

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Gigi Hadid is no stranger to stompy footwear and wore a sturdy pair of black lace-ups with straight-legged cropped jeans in New York. This combo is perfect for when it’s puddle weather (it’ll also help you avoid muddy hemlines).

These jeans hit that sweet spot between the lower calf and ankle that’s ideal for longer hiking boots.

3. Pick Dresses That Swish Just Above the Ankle

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A tip from hiking-boot aficionado Heilbrunner: Don’t be afraid to wear your boots with wafty, spring-ready dresses when the weather warms up. Be sure to choose something that swishes to the mid-calf or ankle (an inch or two of exposed skin is good) and pair it with leather lace-up boots.

A pair of leather hiking boots will give a diaphanous dress like this some bite.

4. Use the Boots to Ground a Heavily Layered Look

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Piling on wintry layers (see Eva Chen’s combination of a polo neck, checked coat and, er, second checked coat) means it’s essential to balance out your bottom half. Clompy Dr. Martens are a perfect match for a double-coat situation.

These boots are extremely durable, though breaking them in can be tricky. Don’t forget to double-up on socks for the first few outings.

5. Pair Them With a Boilersuit and Puffer Jacket

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There’s something to be said for throwing caution to the wind and wearing hiking boots with whatever you please. Caroline Issa’s boilersuit and banana-yellow down jacket shouldn’t work in theory but is nothing short of styling wizardry IRL.

This brand does the best boilersuits in the business. Our money’s on this pink pair.

6. Smart Lace-Up Boots + Trouser Suit = Perfection 

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You can’t be serious—hiking boots with a trouser suit? If I could just point naysayers in the direction of Caroline de Maigret, then I’ll say no more on the subject.

These grungy boots are about as polished as hiking boots get. Wear them with slouchy trouser suits and plenty of attitude à la de Maigret.

7. Match Your Boots to a Long Coat for Elegance

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Tonal dressing might be borrowed from the Kardashians, but it’s worth bearing in mind when it comes to wearing hiking boots in smarter settings. Pair yours with a sweeping coat in roughly the same hue, and no one will do a double take in the direction of your feet.

You can’t go wrong with these cool boots and some black outerwear.

8. Balance Out the "Ugly" With Dainty Accessories

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There’s no escaping the fact that hiking boots are on the clunkier side, so why not balance out the outfit with some fun accessories? Add a dainty bag like Shrimps’ pearl-embellished bag or a sparkling Simone Rocha hair slide for a street style–ready look.

This beaded bag by Shrimps is a fashion-crowd favourite and the perfect foil for hiking boots.

With April showers here, it might be time to dip your toe into the hiking-boot trend. Just remember to balance out those bulky layers and pick jeans that cut off at the ankle for the best results possible.