In primary school, my best friend Sean had a uniform: those iguana tees that donated a portion of the proceeds to WWF, cargo shorts and intense hiking boots (those monkey bars during break were treacherous). Today, I wear hiking boots even when I’m not trekking up the face of a mountain — and I believe that Sean, subconsciously, inspired me. And he’d be excited to learn that he was at least 15 years early to the rising "hikecore" trend. Hiking boots have evolved since our childhood: based on the needs of the 21st century hiker, some are tricked out with Gore-Tex and other technical features like Thermo tech and Nestfit, while others have morphed into sneaker x hiking boot hybrids.
My first traverse was a digital trek through the internet, where I made it my mission to find the right hiking boots in terms of weight and clunkiness. I’m naturally prone to tripping and slipping in normal shoes, so I was on the hunt for something that was lightweight, yet still protected my feet and provided ankle support. My second traverse: taking my found hiking boots through the streets of NYC, where potholes and construction workers served as my switchbacks and subway stairs as my summit. The test wasn’t simply based on stylishness, but on the ruggedness of the boot. In addition to looking super cool, I also wanted to determine whether I could comfortably wear these boots on a long hike. Enter: The Official Michelle Li Mountaineering Rating System. Five mountains means I would wear them up Mt. Whitney, one mountain means I’ll tie them on for a jaunt to the grocery store.
Click through for my weeklong sartorial journey, where I took several hikes, found myself and experienced the natural wonders of NYC.
Monday
A billowy parachute dress + rustic hiking boots = an outfit formula I've been thinking about trying for some time now. I've experienced over a thousand Mondays, and yet I still struggle to dress myself the first morning of the week. This look was easy yet made me feel all dressed up for my work week. These boots are cute for hiking through the city, but my heart can't handle taking them on any actually muddy trail and staining the leather.
Miles Walked: 6 miles
Trip and Slip Count: 3 trips, 1 slip
Rating: ⛰⛰⛰
Cole Haan Women's ZERØGRAND Explore Waterproof Hiker Boot, $212.63, available at Cole Haan
Tuesday
When I initially brainstormed outfit ideas for hiking boots, my mind automatically jumped to styling them with feminine flowy dresses. But trousers deserve hiking boots, too! I went the trusty pyjamas-as-daywear route and styled these sneaker boot hybrids with satin trousers. Do I look like I just stepped out of my tent and am ready for some instant coffee? (The only acceptable answer is yes.)
Miles Walked: 10 miles
Trip and Slip Count: 0 trips, 0 slips
Rating: ⛰⛰⛰⛰
Ganni Hightop Tech Boots, $300, available at Ganni
Wednesday
These boots are described on the Cat Footwear website as "overbuilt" and it's a term that I wish I’d come up with myself. With shoes as quirky as hiking boots, you can also get creative with your sock choices. I chose to match mine with the yellow details on the shoe and my dress. I'm tempted to pick up a hard hat, fluoro vest, crampons and spork (an important eating utensil when on the trail).
Miles Walked: 13 miles
Trip and Slip Count: 3 trips, 2 slips
Rating: ⛰⛰⛰⛰⛰
CAT Footwear Intruder Neutrals, $85, available at CAT Footwear
Bombas Women's Classic Marls Calf, $10, available at Bombas
Thursday
I have a tendency to bring two books (aka 5 extra lbs) when I go backpacking. This outfit is my ode to that not-so-practical bibliophile. She can make her way through the New York Times bestseller list while simultaneously making her way through the Appalachian Trail carrying a heavy load. 10/10 would actually hike the AT with these puppies.
Miles Walked: 8 miles
Trip and Slip Count: 4 trips, 2 slips
Rating: ⛰⛰⛰⛰⛰
Salomon QUEST 4D 3 GTX W, $180, available at Salomon
Friday
This is my interpretation of hikecore, but with non-hiking clothing from my own closet. La Sportiva typically makes rock climbing shoes, which is probably why these hug my feet in all the right places. Naturally, they hug my heart in all the right places as well.
Miles Walked: 7 miles
Trip and Slip Count: 1 trip, 0 slips
Rating: ⛰⛰⛰⛰
La Sportiva Trango TRK GTX Women's, $167.34, available at La Sportiva
Saturday
Gymnast, but make it fashion. Keep in mind that cartwheels and trekking are not mutually exclusive! I loved the colours on these boots, and had a two-hour internal debate about whether I should keep things monochrome or let the colours contrast. I settled on letting the colours clash — a favourite styling tip of mine. Despite their exciting colours, these boots didn't provide my feet with the support I would need for serious hikes. Meh.
Miles Walked: 6.5 miles
Trip and Slip Count: 2 trips, 0 slips
Rating: ⛰⛰
Oboz Juniper Mid BDry Hiking Boots, $110.33, available at REI
Sunday
I probably wore an outfit similar to this in elementary school (just add a Hello Kitty backpack). Unfortunately, the support on these boots had too much support, and dug into the arch of my foot.
After a week of hiking boots, I can say with confidence that my favourite way to wear the technical boot is with something unexpected. Today it’s a bright orange wrap dress, and tomorrow might be a tulle princess dress. This is what makes the hiking boot (surprise!) the ultimate versatile shoe — not just in terms of utility, but also in terms of wearability with non-hiking outfits.
Miles Walked: 10 miles
Trip and Slip Count: 4 trips, 2 slips
Rating: ⛰⛰
The North Face Ultra Fastpack III Mid GTX, $75, available at The North Face
Like what you see? How about some more R29 goodness, right here?
How R29's Fashion Writer Tackled The Cardigan, 3 Ways