I was standing in a hotel room in Minneapolis last February, staring at my open suitcase like it had personally betrayed me. Outside, it was negative seventeen degrees. The wind chill made it feel like negative thirty-something, according to the cheerful local news anchor who seemed oddly proud of this fact. And there I was, with exactly one pathetic merino sweater that suddenly felt about as substantial as tissue paper.
“You’re from Chicago,” my editor had said when assigning me to cover a heritage bootmaker’s factory opening. “You know cold.” Yeah, I know cold. I also know there’s cold, and then there’s Minnesota in February cold, which is a whole different universe of frigid. The pitiful “winter wardrobe” I’d packed was perfect for New York’s relatively mild winter but laughably inadequate for the Upper Midwest. The next morning, I ended up wearing literally every upper body garment I’d brought simultaneously — t-shirt, button-down, sweater, blazer — topped with a massive Carhartt coat I panic-bought at a local workwear shop. I looked like a fashion editor having an existential crisis, which wasn’t far from the truth.
Two months later, I was sweating through my go-to navy tropical wool suit in Austin, wondering why I hadn’t considered that “spring conference” means something very different in Texas than it does in New York. By May, I was getting rained on in Seattle with leather dress shoes that were absolutely not up to the task.
After a year of these climate miscalculations, I finally got smart and developed an approach to packing and wardrobe building that could handle the wild regional variations of American weather. Because let’s face it — in a country where you can experience everything from desert heat to arctic blasts, mountain snow to tropical humidity, often within the same month of travel, you need a system.
Here’s what I’ve learned, the hard way, about building a wardrobe that works whether you’re in Portland or Portland (Maine, that is).
My first revelation was blindingly obvious in retrospect: layers are everything. Not exactly groundbreaking advice, I know. But it’s the execution that matters. The key is creating a collection of pieces that can play nicely together in different combinations while maintaining some kind of coherent style. This isn’t about having specialized gear for every possible weather scenario — it’s about versatility.
I’ve gradually replaced most of my wardrobe with what I call “transition weight” fabrics. Take my favorite sport coat — an unconstructed number in a mid-weight hopsack wool from a small maker in Boston. In New York’s fall, I can wear it with just a shirt. In Chicago’s winter, it works over a thin sweater. In San Francisco’s temperamental microclimate situation, it’s perfect for those weird days that somehow feature both summer and winter temperatures within the same afternoon.
The sweet spot, I’ve found, is in the 8-12 oz fabric range for most garments. Heavy enough to provide some warmth, light enough to not cook you alive if temperatures suddenly rise (I’m looking at you, Denver, with your 40-degree temperature swings). My go-to trousers now are all in this middle weight — tropical wool is too flimsy for real weather, and flannel is a furnace in anything above 60 degrees.
Of course, you need true seasonally appropriate pieces too. But I’ve found I need fewer of them than I originally thought. Two genuinely heavy sweaters, one serious winter coat, and proper boots will get you through most American winter situations when layered strategically with your mid-weight stuff. Likewise, a couple of truly lightweight shirts, one pair of breathable trousers, and appropriate shoes will handle most hellishly hot scenarios.
Color coordination becomes crucial in this system. When everything potentially needs to work with everything else, you can’t have a bunch of wildcard pieces throwing off your combinations. I’ve narrowed my travel wardrobe to a tight palette of navy, gray, olive, and burgundy, with white and blue shirts as the constants. Boring? Maybe. But I’d rather be boring than be the guy sweating through an outfit that’s completely wrong for where I am.
I’ve also become fanatical about researching the actual, practical weather conditions of where I’m going — not just the forecast, but how it really feels. Weather apps are notoriously bad at conveying the lived experience of a place. Seattle’s 55 degrees and drizzly feels completely different than Boston’s 55 degrees and windy. Austin’s 80 degrees has a different quality than New York’s 80 degrees. I now check multiple sources, including texting locals when possible with the very specific question: “What are people actually wearing there right now?”
Look, I’ve made every climate-related wardrobe mistake possible. I’ve been the idiot shivering in a “winter coat” that was laughably inadequate for the actual winter I encountered. I’ve been the sweaty mess in too many layers because I packed for last year’s abnormally cool spring rather than this year’s heat wave. I’ve ruined good shoes in unexpected downpours and found myself desperately shopping for a sweater in a strange city because nighttime temperatures dropped more than predicted.
The worst was probably the week I spent in Colorado a couple years back, working on a feature about American-made outdoor gear. The manufacturer’s PR person had told me we’d be “mostly indoors with maybe a short hike for photos.” That “short hike” turned into a four-hour mountain trail excursion, which I attempted in leather dress boots and chinos because I’d packed for a factory tour, not wilderness expedition. My feet had blisters for two weeks. The photographer got some amazing shots of me trying to maintain dignity while clearly being completely out of my element. One of them ran with the article — my editor thought it was hilarious.
After enough of these misadventures, I’ve developed some specific strategies. I’m now devoted to what I call the “core competence” approach. Rather than trying to pack perfectly for every scenario, I make sure my wardrobe can handle 80% of situations very well, and I don’t stress if I’m slightly under or overdressed for the remaining 20%. Having one outfit that’s perfect for unexpected heat and another for unexpected cold is better than having four outfits that all fall apart if conditions aren’t exactly as predicted.
Materials have become my obsession. Merino wool is basically a miracle fabric — it regulates temperature, doesn’t hold odors, and can be worn multiple days without washing, which is crucial for travel. I’ve slowly replaced most of my basic layers with merino versions. Yes, it’s more expensive, but I’ve worn my favorite merino cardigan everywhere from Montana in October to Mexico City in December, making it worth every penny on a cost-per-wear basis.
For shirts, I’ve become a zealot for high-quality oxford cloth. Not the flimsy stuff that passes for “oxford” at most mainstream retailers, but the substantial, gets-better-with-age kind from makers who understand that a proper OCBD is an investment, not a disposable item. A well-made oxford cloth shirt works across so many temperature ranges it’s almost ridiculous — especially if you get the weight right. Mine go from New York summers (sleeves rolled up, top button open) to Chicago winters (layered under a sweater) without missing a beat.
Footwear might be the trickiest part of the multi-climate equation. I’ve given up on the idea of the perfect travel shoe and instead focus on bringing the right 2-3 options that cover the likely scenarios. My current system revolves around three pairs: suede chukkas (desert boots, essentially) that handle most moderate conditions, proper weatherproof boots for serious cold/wet situations, and loafers for warm weather. All three are Goodyear welted because I’m both practical and slightly obsessive about these things.
Outerwear is where I’ve made the biggest investment upgrades. After one too many instances of inadequate protection, I bit the bullet and spent serious money on a technically advanced coat that doesn’t scream “I’m dressed for Everest.” It’s waterproof, windproof, insulated yet breathable, and — crucially — doesn’t make me look like I got lost on the way to a ski slope. The key was finding technical performance disguised as traditional menswear, a niche that more American manufacturers are finally addressing.
What I’ve ultimately learned is that adaptability beats specialization when dealing with America’s wildly variable climate zones. I’d rather have five really thoughtful pieces that work together in different combinations than fifteen single-purpose garments. My suitcase is lighter, my morning decisions are simpler, and I spend a lot less time panicking in hotel rooms wondering how I’m going to avoid freezing/sweating/getting soaked.
Yes, my friends tease me about my weather obsession before trips. “Jack’s checking the hourly forecast again,” they’ll groan when I’m glued to weather apps the week before traveling. But you know who’s not shivering through dinner or sweating through meetings? This guy. And in my line of work, nothing undermines your credibility quite like visibly losing the battle with local conditions while trying to write authoritatively about style.
Building a nationally functional wardrobe 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 that master tailor or assessing that new collection when all you can think about is how badly your feet hurt or how much you’re sweating. Been there, wrote that article, never want to do it again.
