I was wearing shorts in Minneapolis last February when I realized I fucked up. Packing Shorts was sort of my Louis Sweatshirt of doom. I was standing in my mid-tier hotel staring blankly at my suitcase as if it had just laughed at me.
It was negative seventeen degrees out. Well, minus seventeen without wind chill, which dipped even lower. The news anchor had covered his mouth with obvious glee. “Feels like seventeen degrees below zero!” Happy Independence Day, Minneapolis.
At that moment I looked down at the lone thin hoodie I had packed and internally said “sweet jesus I am going to die.” Emma was doing freelance photos for this heritage bootmaker and had to cover their new factory opening. Last-minute she couldn’t make it and asked if I wanted to swing by and cover it for the site. “You’re from the Northwest,” she said. “You know cold.” Sure buddy, I know PacNW cold.

Forty degree cold with tons of moisture in the air that just feels like cold and rain when you’re used to Southern California summers.
I didn’t know minus f*cking seventeen cold with wind chill temps that made you question your immediate mortality. When I woke up the next morning to go to work I threw on every layer I had with me. Shirt, flannel, hoodie, denim jacket, and this insanely bulky Carhartt coat I bought from some workwear shop across the street from my hotel after my realization from the day before.
I looked like Steve – our Senior Editor – returned every item in his boutique shopping spree and put on an entirely new outfit comprised of donations from his crazy artist friends while blindly walking around Goodwill. The guys working at the boot factory were chill about it, but I could see them stifling laughter as I walked through the door looking like Walter White’s burlier hipster brother. Two months later it happened in reverse on a trip to Austin. Emma and I had gone to cover some design conference thing and I once again neglected to properly check what “spring” was like in Texas versus Portland, Oregon.
Spoiler alert: They’re not the same thing. I was lugging around this black heavyweight hoodie and dark denim combo all day sweating through my shirt and struggling to hold my phone with sweaty fingers. Again, not ideal.
Last year I spent a summer week in Seattle – which should have tipped me off that I had no idea what seasons were like outside the PNW – and got drenched walking from my AirBnB to some sneaker boutique I was profiling. My sneakers absorbed a gallon of water from the sidewalk and my favorite vintage Jane’s Addiction shirt translucent. Owner of boutique shook his head at me when I walked in sagging and dripping on his showroom floor. “First trip to Seattle?” He asked. “Nope,” I laughed. “Just clueless when it comes to weather, apparently.” After YEARS of these disasters across America I finally took notice and started to create a capsule wardrobe that could work in any season while traveling across the country.
The US is a big motherf*cker and the weather ranges wildly from coast to coast, mountain to mountain, and year-over-year at the same location. You can drive from semi-desert heat to full-on arctic assault within a day’s drive if you work in certain industries. I had to come up with a plan because ruining your entire trip because you’re freezing your ass off is no bueno and unprofessional AF.
Lesson Number One: Layer correctly.
What happens if it’s 65 degrees with zero humidity in January in Ohio? You’re fucked because you didn’t pack anything you can layer pieces together to keep warm, and everything you have that’s summer appropriate is white and covers a month of dates on your vacations schedule. “` TLDR: Think about building middle-weight everything. My entire travel wardrobe is built around middle-weight clothing that can perform adequately in multiple temperature ranges rather than being specifically tailored for one kind of weather.
Take this canvas jacket I picked up from this small company in LA. It’s heavy enough that I can wear it over a hoodie if I need some warmth, but won’t trap you in a sweat cage if it decides to warm up unexpectedly. I’ve worn this jacket in Portland, OR in December and Denver, Colorado in October.
This was when it clicked for me. I slowly started re-making my wardrobe around these “middle-weight” pieces. Heavier hoodie than you’d typically find at Uniqlo, but not so heavy that you’d die if you wore it in sixty degree weather in February.
Same thing with shirts. No more thin crap from American Apparel that looks like a chuck tee except $60. My go-to when I’m traveling for work is now heavy oxford shirts from wherever we’re visiting.
They’re more heavy duty than your basic shirt, but won’t completely cook you if it’s an unusually warm spring day. Everything about this build is based around these middle weights that you can use to build both warmer and cooler outfits depending on Mother Nature. “` Of course you’ll still want some items that are specific to seasons. I have this insanely thick wool sweater I picked up from this shop in Maine.
It’s probably warm enough to handle actual winter conditions. And I always bring a quality pair of waterproof boots now. But because I have so many middleweights that I can *layer* under these specialized pieces, I don’t need a ton of them.
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Two really warm layers, a heavy coat, and waterproof boots will get you through any severe winter with proper layering. You can apply that same mentality to summer. Pack a couple lightweight t-shirts, a pair of summer shorts that aren’t athleisure, and minimal shoes that can handle high temps and you’re good to go in combination with your regular wardrobe.
Color palette also became incredibly important when I started focusing on everything having to work with everything else. Sure you can pack one funky shirt that only matches with that one specific hoodie, but now you can’t wear thatsts when you have to suddenly change how you layered due to weather changes. I stick to navy, gray, olive, and black as staples now with white and chambray shirts as constants.
Looks boring as hell when laid out, but trust me when I say you’ll look like a dipshit if you don’t follow this rule. Research weather where you’re going, not where you’re departing from. And I don’t mean look at the forecast night before you leave.
Don’t trust these weather apps, they’re garbage. Seventy-five degrees in Seattle and fifty-five degrees in Boston both hit you different because of humidity and wind. 90 degrees in Phoenix does not feel the same as 90 degrees in Miami.
Look at reviews of where you’re going, look at forums on Reddit to see what people are *actually* wearing that week/year. I’ve done it all. Went to a gallery opening in Brooklyn once wearing jeans and a sweater because my winter coat was really just a bulky light jacket.
Once I showed up to Atlanta in April sweating through my shirt because I “packed for last years weird warm spring” and forgot to Google weather trends for 2017. Ruined a good pair of sneakers hiking in the rain because I didn’t pack any waterproof shoes. Had to buy $80 button-ups at Hudson Station because overnight temps dropped forty degrees from the day’s high.
Once I legit bought a new hoodie in Iceland because I ran underdressed during a tour. Worst was when I was down in Colorado a few years ago checking out an outdoor gear company. PR told us it would be “predominantly indoors with maybe an outside photo opportunity.” We ended up hiking/horse-back riding for four hours straight up some mountain. I did the whole thing in leather boots and jeans because my outfit was “business casual, w/optional outdoor activities.” Lost shoes by the end.
Soaked through my clothes. Hose couldn’t even touch my feet for the amount of blisters I was rocking. Photoshop killed me. My editor used the picture of me squatting while holding my ripped feet for the article because he thought it was hilarious.
The goal is now “good enough.” Packing one awesome outfit that’s 100% summer and another that’s 100% winter means you’re screwed if it warms up in the middle of January or it’s unseasonably cold during Summer clothes.” Opt instead for pieces that can do 80% of the job really well. Hope for the best, pack slightly less than you think you need, and only stress about the weather when you see the forecast above 60 degrees. “` I also started really nerding out over materials. Wool, specifically Merino wool, is a miracle fiber.
It regulates your temp, it hardly smells after days of wearing, and it performs across SO many different temperatures. Slowly replaced just about all of my base layers with Merino versions. Yes, they’re expensive as shit.
But I’ve worn that big Merino hoodie from Maison Margiela knockoffs in Montana in October to Mexico City in December. Cost per wear, son. Shirts became all about heavyweight oxford cloth.
Not that thin-ass underwear material blouse Quicksilver thinks is oxford. I’m talking heavy-duty menswear oxford shirts that only certain brands really understand how to make.

An oxford cloth button up can be your winter layer, rolled up for summer, and is infinitely comfortable year-round.
Shoes are honestly the worst and I still haven’t quite perfected my formula. Gone are the days of me trying to find “the one” sandal/shoe/tommy-hawk-heel that I can wear everywhere. Now I just try to pack the two or three shoes that will cover most scenarios.
Leather shoe that can handle cool weather. Waterproof shoe for rain. And minimal shoe for hot weather.
Oh, and they all have to be resoleable because I’m not stupid. “` If you’re anything like me you’ll spend more money on an outer shell than any other article of clothing. I finally broke down and purchased a high end/down jacket a few years ago after countless trips where my outer layer wasn’t quite enough. It’s technically perfect – waterproof, windproof, insulated yet breathable – and doesn’t scream upward facing hummus pouch like every other “travel jacket” on the market seems to these days.
The hard part was finding one that had all the travel/performance features hidden inside of a nerf jacket. Most American brands have finally caught on to that concept and are offering more options than ever for men.



