How I Stopped Getting My Ass Kicked by Weather (And Built a Wardrobe That Actually Travels)

Okay, so picture this: I’m standing in some budget hotel in Minneapolis last February, staring at my suitcase like it just told me my entire life was a lie. Outside it’s negative seventeen degrees – not including wind chill, which apparently made it feel like the surface of Mars or something equally hostile to human life. The local news guy seemed weirdly excited about this, like breaking temperature records was some kind of civic achievement. Meanwhile, I’m looking at the single thin hoodie I packed thinking, “Well, I’m definitely going to die here.”

See, Emma had this freelance gig photographing some heritage boot company’s new factory opening, and she couldn’t make it last minute, so I offered to go document it for my blog. “You’re from the Northwest,” she said, “you know cold weather.” Yeah, I know Pacific Northwest cold, which is like… wet and forty degrees. I don’t know Minnesota-in-February cold, which is apparently a completely different category of atmospheric hostility.

The next morning I ended up wearing literally every piece of clothing I’d brought – tee shirt, flannel, hoodie, denim jacket – topped with this massive Carhartt coat I panic-bought at some workwear store near the hotel. I looked like someone having a breakdown at Goodwill, which honestly wasn’t far off. The boot factory guys were super nice about it, but I definitely caught a few smirks when I showed up looking like the Michelin Man’s hipster cousin.

Two months later, same problem but opposite direction. I’m at some design conference in Austin wearing my go-to dark denim and heavyweight hoodie combo because it was “spring” and I figured Texas spring couldn’t be that different from Oregon spring. Wrong. By noon I was basically drowning in my own sweat, trying to take notes while my phone kept sliding out of my wet hands. Not exactly the professional image I was going for.

Then there was Seattle in May – yeah, I know, I should have known better about Seattle – where I got completely soaked walking from my Airbnb to the sneaker boutique I was supposed to profile. My canvas sneakers turned into sponges and my favorite vintage band tee became see-through. The shop owner took one look at me dripping on his pristine white floors and just shook his head. “First time in Seattle?” he asked. Nope, just perpetually unprepared for reality, apparently.

After a year of these climate disasters, I finally got my act together and figured out a system that could handle the insane weather variations you deal with traveling around America. Because seriously, this country is massive and the weather makes no sense – you can go from desert heat to arctic conditions within the same week if you’re traveling for work or whatever.

The big revelation was layering, but not in the obvious “wear more clothes when it’s cold” way that everyone already knows. It’s about building a collection of pieces that actually work together instead of just throwing random items at the problem. I mean, I used to pack like I was shopping different sections of a store – one “winter outfit,” one “summer outfit,” one “rain outfit” – without thinking about whether any of it could mix and match when conditions inevitably turned out different than expected.

Now I focus on what I call middle-weight everything. My entire travel wardrobe revolves around pieces that can work in multiple temperature ranges instead of being optimized for one specific condition. Like this canvas jacket I got from this small brand in LA – it’s substantial enough to provide some warmth over a hoodie, but breathable enough that I don’t die if it unexpectedly gets warm. I’ve worn it everywhere from Portland in December to Denver in October.

The fabric weight thing became kind of an obsession. Most of my hoodies now are in that perfect middle range – heavy enough to actually keep you warm, light enough that you won’t cook if the temperature jumps twenty degrees during the day (which happens constantly in places like Colorado, by the way). Building a wardrobe around these transition weights means I can layer up or down without looking completely ridiculous.

You still need some season-specific stuff, obviously. I’ve got this heavyweight wool sweater from this brand in Maine that’s basically armor against real cold, and proper waterproof boots that can handle actual winter conditions. But I need way fewer specialized pieces than I used to think. Two really warm layers, one serious coat, and decent boots will get you through most extreme cold situations when you layer them with your regular middle-weight stuff.

Same thing for hot weather – couple of lightweight tees, one pair of shorts that don’t look like athletic wear, and breathable sneakers or minimal shoes will handle most brutal heat when combined with your normal rotation.

The color coordination became crucial once I realized everything needed to potentially work with everything else. Can’t have random bright pieces that only work with one specific outfit when you might need to completely reorganize your layers based on unexpected weather. I basically stick to navy, gray, olive, and black now, with white and chambray shirts as the constants. Boring? Maybe. But I’d rather be boring than be the guy who looks completely out of place because his outfit fell apart when conditions changed.

I also became super neurotic about researching the actual weather where I’m going, not just glancing at the forecast the night before. Weather apps are terrible at conveying what it actually feels like to be somewhere. Seattle’s fifty-five and drizzly hits completely different than Boston’s fifty-five and windy. Phoenix’s ninety degrees is not the same as Miami’s ninety degrees – trust me on that one.

Look, I’ve made every possible weather-related mistake at this point. I’ve been the idiot shivering outside some gallery opening because my “winter coat” was basically a windbreaker with delusions. I’ve sweat through meetings because I packed for last year’s weirdly cool spring instead of checking if this year was going to be different. I’ve destroyed good sneakers in unexpected rain and found myself desperately buying overpriced basics at airport shops because nighttime temperatures dropped forty degrees from the daytime high.

The absolute worst was probably this trip to Colorado a couple years ago when I was documenting some outdoor gear company. The PR person said we’d be “mostly indoors with maybe a quick photo op outside.” That “quick photo op” turned into a four-hour hike up some mountain trail that I attempted in leather boots and jeans because I’d packed for conference rooms, not wilderness expedition. My feet were destroyed for weeks. The photographer got some amazing shots of me clearly dying while trying to maintain some dignity, and my editor actually used one in the article because he thought my suffering was hilarious.

After enough of these disasters, I developed what I call the “good enough” strategy. Instead of trying to pack the perfect outfit for every possible scenario, I make sure my stuff can handle eighty percent of situations really well, and I don’t stress about the remaining twenty percent. Having one combination that works for unexpected heat and another for unexpected cold is way better than having multiple outfits that all fall apart if conditions aren’t exactly as predicted.

Materials became my new obsession. Merino wool is basically magic – it regulates temperature, doesn’t smell even when you’ve worn it for days, and works across crazy temperature ranges. I’ve slowly replaced most of my base layers with merino versions. Yeah, it’s expensive, but I’ve worn my favorite merino hoodie from Montana in October to Mexico City in December, so the cost-per-wear math definitely works out.

For shirts, I’m completely devoted to good oxford cloth now. Not the thin garbage that most brands call “oxford,” but the substantial, gets-better-with-age kind from companies that actually understand what they’re making. A well-made oxford cloth shirt works in so many different conditions it’s almost ridiculous – rolled sleeves in summer, layered under sweaters in winter, perfectly comfortable everywhere in between.

Footwear might be the trickiest part of this whole system. I gave up on finding one perfect travel shoe and instead focus on bringing the right two or three pairs that cover likely scenarios. Usually some kind of leather boot that can handle moderate weather, actual waterproof boots for serious conditions, and minimal sneakers for warm weather. All resoleable because I’m practical and slightly obsessive about buying things that last.

Outerwear is where I finally bit the bullet and spent real money. After too many instances of inadequate protection, I invested in a technically advanced jacket that doesn’t look like I’m headed to base camp. It’s waterproof, windproof, insulated but breathable, and – most importantly – doesn’t make me look like I got lost on the way to REI. The key was finding performance features hidden inside normal-looking menswear, which more American brands are finally figuring out how to do.

What I’ve learned is that adaptability beats specialization when you’re dealing with America’s completely insane climate variations. I’d rather have five thoughtful pieces that work together in different combinations than fifteen single-purpose items. My bag is lighter, my decisions are simpler, and I spend way less time panicking in hotel rooms wondering how I’m going to survive the local weather.

Yeah, Emma makes fun of me for obsessing over weather forecasts before trips. “Keith’s doing his weather research again,” she’ll say when she catches me checking multiple apps and reading local forums about what people are actually wearing. But you know who’s not freezing through dinner or sweating through meetings? This guy. And when you’re trying to document style and culture professionally, nothing kills your credibility quite like visibly losing the battle with basic environmental conditions.

Building a wardrobe that works nationally isn’t just about comfort – it’s about being present enough to do your job properly. Because trust me, you can’t focus on interviewing some craftsperson or documenting some brand’s story when all you can think about is how much your feet hurt or how badly you’re overheating. Been there, written those articles, never want to repeat that experience.