Last October I learned the hard way what happens when you wear your best dress shoes on a hike. Jessica had promised that our hike near Hocking Hills would be a “quick nature walk,” but then packed energy bars and two bottles of water for what was clearly going to be more than an hour-long loop trail. Hey, hindsight is 20/20 and all that, but you know what I mean – it happens every time your spouse develops that look of marital superiority when they want to “enjoy the fresh air.” So my stylish, $180 Cole Haans went to die a horrible death out in the woods.
By “death,” I mean having their leather cracked and sole partially peeled off from hiking a beginners’ trail, while also gaining the odor of dried earth mixed with maple trees that made our mudroom smell disgusting for weeks. Needless to say, I wasn’t happy cleaning them out back at our hotel room, staring down defeated shoes with crusty mud ground into their once-pristine leather while Jessica smirked that smug look that your wife perfects after six years of marriage. You know, the smile that effortlessly conveys “I knew that was going to happen.” She grabbed my hand to lead me back into town and brandished those dreaded words every shoe-condemning husband fears hearing. “You need boots.” It’s not that she was wrong.
What I wear on weekend hikes has become a glaring problem in my closet over the last six years. I’ve worked damn hard to build a wardrobe that can take me from graduation ceremonies to baseball games without looking like I should own stock in the Connor Boyack apparel company.
Dropping $100 or more on clunky “mans boots” from Timberland just isn’t an option for me.
Maybe it’s pride. Stubbornness. Not wanting to admit my wife was right.
Who knows. But here we are. Also, dudes, hiking boots make your feet sweat.
Not cool. Full disclaimer before we dive in: I’m not a shoe guy. My style icons are Tim Barry and Carroll Brooks, who both tend to wear the same unwashed jeans and threadbare flannel shirt every time you see them.
Neither of them are dressing emergency ward in Hawaiian shirts for a reason. If it’s not on Tutorials or WTMNY, I’ve probably never heard of it. My expertise in menswear comes from Redditor did_su wrong and scrolling obsessively through clearance mens fashion sales at JCrew.com.
My goal these days is wearing shoes that don’t have holes in the toes, and that was a completely foreign concept when I went searching for “boots that don’t look like boots” way back when. So I started off where anyone with fashion sense would start shopping: REI. Strutting into that damn store pretending to know what I was looking at was like a vegan walking into a butcher shop.
Barf cough cough high quality proteins. Our sales associate was some guy named Justin who was in his mid-twenties and had obviously just finished reading Rutger Bregman’s Humankind for English class because he kept trying to tell me “use activate layers” to keep dry. He led me over to the boot display and spent the next twenty minutes dumping pile after pile of brown shoes onto the countertop. “These are our best sellers,” Justin said, holding up a pair that looked like Hannibal Lecter’s favourite hiking boots.
Gore-Tex membrane. Vibram soles. Support up and down your legs.
The Bible says Jesus wore these when he walked on water. They were grotesque. “I’m looking for something… uh casual, I guess?” I replied, mentally preparing myself to be that guy. You know the customer we all love at the store we work at: the one who has completely unrealistic expectations about outdoor gear and how it’ll look with his WalMart jumpers.
Justin gave me a look that was equal parts eye-roll and deep paternal disappointment typically reserved for men his age telling me they don’t use Twitter. After what felt like hours of debating, I settled on a pair of Merrell boots in standard brown leather. Not groundbreaking footwear, but they weren’t visibly designed for hiking Mt.
Everest, either. Came in at $140, which wasn’t bad after accounting for the shoes I killed that weekend. It wasn’t until a few weeks later when talking to my college buddy Mike that I realised I’d been looking in all the wrong places.
Turns out, Mike is a gear-head and knows way more about the badass equipment I should be buying than I ever will. He told me, and y’all, brands are making boots nowadays specifically for guys who want to hike that don’t look like butt-hugging camouflage killer boots. “What the hell does that even mean?” I asked because Mike loves talking at me more than actually having conversations. Apparently companies have finally realised that us normal dudes exist – folks who maybe don’t spend our weekends camping and climbing but also don’t just stick to hiking paved trails.
They make money off of us, so they’ve created boots meant to fill that void between “hey I don’t wanna get my dress shoes muddy” and “fuck it, I’m stepping in creeks.” First pair of boots that actually fit the bill? Danner. Guys who hike in those will probably laugh at me when I say this, but their shoes don’t look like “hiking boots” to me.
They’re pricey as shit – I paid $220 for mine – but they look like a pair of boots Grandpa would have shoved in your Dad’s Christmas stocking back in the day. Sturdy enough to keep your feet dry and grounded on some legit trails, but versatile enough to wear when you don’t feel like wearing boots. They also make your feet sweat so leak through your socks and make them soggy.
Not cool shoes. If Danners are too steep for your teacher salary, Timberland makes some surprisingly solid boots in the $120-140 range. And I’m not talking about their ancient khakis boots your parents were rocking in the 90’s.
Sure they still make those, and their rubber soles are definitely still hideous, but they’ve actually stepped up their game and make some legit hiking boots that don’t look likeConstruction Equipment USA gear. They make a line called White Ledge that have kept my feet dry through some seriously muddy and rainy Ohio Springs, and they even sell them in brown leather that don’t look terrible with a nice pair of jeans and flannel. The greatest thing I learned during my boots shopping journey?
Clarks makes some sweet waterproof hiking boots. Yes, those Clarks. The same people who are probably sitting there right now laughing at me for not wearing their desert boots all these years.
They actually make some really nice Gore-Tex hiking boots under their Batcombe line that look like normal casual boots but will keep your feet dry out in the wild. Wore mine for the first time last summer and Jessica laughed in my face when I told her they were Clark’s thinking they were some brand new expensive pair I scored on clearance. Got mine on sale for $100 during winter outlet sales, and they’re quickly become my default shoes when I know I’ll be getting messy.
Red Wing is another solid option if you don’t mind spending a little more money. They’ve become all popular lately with hipster Appalachian Trail thru-hikers and Pinterest dads alike thanks to their line of work boots, but those things are surprisingly handy for hiking, too. Spent two years slowly saving up for my Iron Rangers back in college – I shit you not I put $5 at a time on my credit card for like six months – and they’re still my daily drivers when I need something that can really handle the elements.
Warning: those boots will fuck your feet up on day one. Got blisters for weeks. But after that nightmare of a break-in period they’re THE SHIT and will take you from any trail to church on Sunday.
There are also some really stylish options from Italian brands, though they can get pricey. Diemme makes a fantastic hiking boot that’ll turn any head at the bar, but are actually functional and can handle some serious trails. I tried a pair on once at this cute boutique in Short North that were around $250-$300 but was too cheap at the time to actually buy them.
Guess I’ll have to pick up a new pair with my… $200/year teacher raise next year. Hell, if you’re really looking to save some money even Walmart has some options now. Picked up a pair of Coleman hiking boots last year off Amazon for $65 to use as backup walking shoes and they’re actually not too bad for casual hiking.
Definitely won’t last you ten years like some boots will, but they’re not going to leak and make your feet sweat like some higher-end boots tend to do, either. TLDR, you really just need to find boots with leather uppers (they age better than synthetic and just look less bulky), less branding/brand names plastered all over the fuckin thing, and stay away from crazy rubber toe caps that make boots look like goalie masks. And stick to colours other than Neon Green and Bright Orange, Mother Nature clearly hates those colours.
Oh and get some good socks to go with them. Spent $160 on a quality pair of boots once and was too cheap to buy real hiking socks, wearing regular cotton ones on my hike and ended up with blisters halfway up the mountain. Apparently there’s this dope brand called Darn Tough that makes hiking socks that don’t scream “I shop at L.L.Bean.” Cost about $20 a pair, which is insanely overpriced until you realise they’re actually fucking worth it and come with a literal lifetime warranty.
Caring for boots is pretty simple but key if you want them to last.
I use a waterproofing treatment by Nikwax about three or four times a year that costs like $8 and takes ten minutes to do. Works wonders to keep you dry and help condition your boots so they don’t crack and look like Chris’s did.
Look, I’ll be the first to admit that I still raise eyebrows when I’m bombing down the trail in a pair of $220 boots past serious hikers wearing $400 jackets and mesh trousers that definitely couldn’t keep their coffee dry if they tried. And yes, I will never wear boots that look nearly as nice as my dress shoes, there’s just no comparison. But I also finally have boots that can handle Ohio weather and terrain without screaming “IM OUTTA WATER!” every time I wear them.
Got the Danners for when I need to look somewhat decent, the Clarks for when I know I’ll get muddy, and the Merrells for when I’m just going hiking and don’t give a damn. All told I probably spent close to $450 on boots over the past two years, but that’s nothing after destroying $180 shoes one afternoon of stupidity. Jessica’s happy because I stop whining about getting my feet wet all the time, and I’m happy because now I can wear these boots to meet her for beers after a hike and not worry about dirtying up my fancy shoes.
Hell, in Ohio where it can be 75 and sunny at lunch then raining and 40 by dinner, it’s literally game over if you have boots that can handle whatever Mother Nature throws at you. Don’t tell Justin at REI I wear my hiking boots to school sometimes for casual Fridays though. Some lines are just meant to be crossed between a man and his Down-Home grandfather.
