Last week I was waiting outside of my Chicago office building and witnessed a gang of tourists get obliterated by one of our notorious spring storms. You know the ones I’m talking about, when it’s sunny and sixty-five degrees one minute, and then all of sudden it’s raining sideways and forty-five degrees the next. They were soaking wet since they were wearing shorts and t-shirts and trying to huddle under any dry overhang they could find.
I felt bad for them, but not because I’ve ever been that oblivious to weather. No, I sympathized with them because, over time and through trial and error on my style journey, I had learned how to properly layer in a way that allowed me to not look like that dumbass. Learning how to properly layer was one of those skills that I learned the hard way.
Back when I was interviewing for my first real post-college job in Chicago three years ago, I went to my first interview wearing just a dress shirt under a thin “professional” style peacoat that I bought from Target. I remember sweating through my shirt twelve blocks from the train station to my interview in twenty-degree weather because my jacket wasn’t actually windproof.
When I finally arrived ten minutes late the receptionist pointed me to a chair and handed me a tissue as if I just ran a marathon.
Needless to say, it was not the impression I wanted to give during an interview. I walked away knowing that I needed to learn how to layer, like, yesterday. Like anything new though, learning how to layer wasn’t as easy as it looked.
I spent weeks wearing what I thought was proper layering. At first I thought more layers = better. Wrong.
Wearing too many layers made me look like Chunk from the Princess Bride. My girlfriend (now wife) even told me once that I looked “a little bulky”. Nice.
But she was right. I didn’t need four-ten layers of clothing on top of me, I just needed to figure out how to make them work together. The biggest revelation came when I started studying how my favourite dudes dressed and noticed they all had one thing in common – they were never overdressed or underdressed.
Ever. No matter how hot or cold it was outside, they were always comfortable. I always admired that about older guys.
Then one day, when feeling particularly inadequate about my outfit rolling around in my head, I asked my boss (a nice older gentleman in his fifties) how he always “nailed it” with his outfits. He laughed nervously and said his dad taught him when he was younger that it wasn’t about how many shirts you own, it was about having the right ones. That sentence has stuck with me ever since.
I began studying how to properly layer so I could achieve the same style as my idols. It all starts with your base layer. Unfortunately this was where I was doing most of my mistakes.
I always started with a cotton t-shirt as my base layer because that’s what was comfortable and I had dozens of them from college that didn’t cost me anything. Cotton t-shirts aren’t great because they retain moisture when you sweat or if it rains outside. They also don’t insulate very well which is key to staying warm when it’s cold outside.
Solution? Merino wool base layers. Merino wool is a miracle fabric.
It allows you to build outfits from the ground up without worrying about being overdressed or underdressed later. My first ever merino base layer changed my life. I purchased it at Uniqlo for I think $40 andremember thinking to myself how crazy I was spending that much on “just a shirt”.
I compared it to my other cotton tees I had that were only $5 for a five-pack at H&M. But this shirt was different. It fit snug but not too tight.
The fabric wicks away moisture so no matter how hot I got it never felt sticky or uncomfortable. I wore it on one of the hottest days in August when I was moving and had to carry boxes all over the city. I was soaked in sweat at the end of the day but my shirt smelled good and never once felt heavy or damp.
If only my other shirts could’ve done that. It was the first step towards kicking my caffeine addiction… to cotton. Now I have 6-7 different merino wool base layers in different weights that I live in.
Building off your base layer is where you can start to have some fun with your wardrobe. Middle layers are your temperature regulating layers. These are the pieces you’ll likely be adding or taking off throughout the day depending on the office temperature or if you’re moving between indoors and outdoors.
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My roommate convinced me to pick up some lighter jumpers but once I found cardigans I never looked back. I hated the look of cardigans for the longest time because I thought they looked too old-fashioned. However, they’re actually great for layering.
You can easily open them up when it gets too warm, but also throw them off your shoulder or take them off completely without messing up your hair. They usually have pockets too which is great for keeping your phone and keys. I found this beautiful one at J.
Crew Factory for $30 on sale and it’s 100% merino wool and navy blue. I wear this thing at least twice a week and haven’t grown tired of it in two years. It goes with literally anything and matches almost all of my blazers, look great over button ups, and pairs nicely with plain t-shirts.
Lastly, you need an outer layer that actually works. No more “wow that jacket looks great but couldn’t keep me warm if my life depended on it” type of pieces. I learned this lesson early when I bought a cheap linen-blend blazer for $80 my first winter in Chicago.
I looked great trolling around downtown in it but the second I stepped outside for the twenty minute walk to work I instantly froze. From that day on I vowed to never underestimate wind chill again. So I broke the bank on a sturdy wool coat from Brooks Brothers factory store for around 60% off.
It was still more than I wanted to spend for a jacket but three winters in and she’s still going strong. Plus, it actually fits in my car during the winter instead of taking up half of my trunk like my old black denim jacket. There’s one more thing about layering that most guys don’t realise.
How each layer interacts with the next is just as important as picking the right layers. You can’t just randomly throw on a bunch of clothes and hope it works. Things like necklines have to somewhat match or it just looks stupid (crew neck over a v-neck isn’t flattering) and your colour combinations need to be cohesive because chances are you’ll need to take your middle layer off at some point during the day.
I learned that lesson the hard way when I wore a bright red jumper under a navy blue cardigan under a light grey blazer for work. Long story short, I had to take my cardigan off during a meeting and suddenly felt like I was representing the American flag. These days my layering game is on-point.
My typical uniform is something along the lines of: Merino wool base layer – tank or t-shirt. Stick to navy, grey, and white so they match under everything. Middle layer – cardigan, light jumper, or “shirt jacket”.
Love the thicker button-ups from Taylor Stitch and Universal Works that aren’t heavy like actual shirts, but thicker than most button-ups. Great for those in-between days where you’re not sure if it’s cold out or not. Outer layer – winter = wool coat.
Every other season = lightweight jacket. The beauty of layering is that you have options. Some days I leave the house feeling like it’s winter outside and come home with half my layers off because it’s hotter than I thought or I was stuck in an office building with the heat cranked up.
Layering is about being prepared for anything. One of my favourite parts about getting dressed each day is knowing that I can adjust my outfit to my environment. Plans change and suddenly you’re going from a meeting in the office to lunch outside.
No problem, just ditch the blazer and keep the cardigan. Office AC gets blasted and you’re freezing.
Easy fix, grab your jumper from your desk drawer and add that on.
Layering allows you to adjust on the fly and never be overly dressed or underdressed for any occasion. Moral of the story? Invest in good pieces that you know will last.
Spend a little extra on that wool coat knowing that you’ll be able to wear it for the next five winters. Don’t be cheap when it comes to your merino wool base layers. $40 might sound like a lot for “just a shirt”, but if you’re wearing that shirt as your base layer 5+ days a week you’ll quickly realise that it costs less per wear than your $5 IKEA shirts. My friend Dave likes to call that “cost per wear”.
Anyway, next time you see a dude ruining his outfit because he’s sweating through his undershirt and will inevitably be cold later because he didn’t bring a jacket, give him a little tip. Don’t do it in a creepy “HEY DUDE YOUR COMING DOWN WITH THE BIG THREE” kinda way, but just point out that maybe he should’ve brought a jacket. I know I would’ve appreciated that when I was younger.
Hell, I’d still appreciate it now if someone said “Hey man, maybe wear a freaking jacket next time”. Layering is one of those game-changing skills that once you know, you know.
