Last week I was standing outside my office building in Chicago watching this group of tourists getting absolutely destroyed by one of those sudden spring storms we get here. You know the type – sunny and 65 degrees one minute, then boom, sideways rain and 45 degrees the next. These poor people were in shorts and t-shirts, huddled under whatever overhang they could find, looking miserable. Meanwhile, I’m standing there completely comfortable because I’d learned something crucial during my style journey: proper layering isn’t just about looking good, it’s about not being that guy who’s freezing or sweating his way through the day.
I actually learned this lesson the hard way during my first real job interview in Chicago three years ago. Showed up in January wearing just a dress shirt under a cheap peacoat because that’s what I thought “professional” looked like. Walked twelve blocks from the train in 20-degree wind, arrived looking like I’d been through a blender, sweating from the walk but also somehow still cold. The receptionist took one look at me and offered me a tissue. Not exactly the impression I was going for. That’s when I realized I needed to figure out this whole layering thing, and fast.
The thing is, layering seems simple until you actually try to do it well. I went through this phase where I thought more layers automatically meant better, so I’d pile on everything I owned and end up looking like the Michelin Man’s younger brother. My girlfriend at the time gently suggested I looked “a bit bulky” which was her polite way of saying I looked ridiculous. She wasn’t wrong – I was wearing a t-shirt, then a button-up, then a sweater, then a hoodie, then a jacket. It was like Russian nesting dolls but way less charming.
The breakthrough came when I started paying attention to how guys who actually looked good were doing it. There’s this older guy at my office – probably in his fifties, always looks put-together – and I started noticing how he never seemed uncomfortable regardless of what the weather was doing. One day I just asked him about it, and he kind of laughed and said his dad had taught him that the secret wasn’t about having more clothes, it was about having the right clothes that worked together.
That conversation changed everything for me. Started researching proper layering like it was my job. Turns out the whole system starts with your base layer, and this is where I’d been screwing up big time. I was wearing cotton t-shirts under everything because they were cheap and I owned a bunch from college. But cotton is terrible when it gets wet – whether from rain or sweat – and it doesn’t regulate temperature at all. Switched to merino wool base layers and suddenly everything else started working better.
I remember my first good merino t-shirt. Cost me like $40 from Uniqlo, which felt insane at the time because I was used to buying five-packs of Hanes for the same price. But man, the difference was immediately obvious. Wore it during a particularly brutal August day moving apartments, and even though I was sweating like crazy, the shirt never felt gross or clingy. My old cotton shirts would have been soaked and disgusting within an hour. The merino just… handled it. Now I’ve got maybe six or seven merino base layers in different weights and colors, and they’re honestly some of the best money I’ve spent on clothes.
The middle layer is where things get interesting, and where you can actually show some personality. This is your temperature regulation zone – the part you’ll be adjusting most often. I went through a phase where I thought this meant heavy sweaters, but that’s not right either. You want something substantial enough to make a difference but light enough that it doesn’t add bulk or make you look like you’re prepared for arctic exploration when you’re just going to Target.
Cardigans became my secret weapon here, even though I initially resisted them because they seemed kind of old-fashioned. But they’re actually perfect for layering – you can unbutton them as needed, take them off easily without messing up your hair, and they’ve usually got pockets for your phone and keys. Found this great one at J.Crew Factory for like $30 on sale, navy blue merino blend, and I’ve probably worn it twice a week for two years. It works under blazers, over button-ups, with t-shirts, whatever. My mom saw me wearing it during Christmas and said I finally looked like I had my life together, which I think was a compliment.
The outer layer is where you can’t mess around. This needs to actually protect you from weather while still looking like you put some thought into it. I learned this lesson during my first Chicago winter when I bought this jacket that looked great but had zero wind resistance. Looked sharp walking to the train, but by the time I got to work I was basically hypothermic. Spent way too much money on a proper wool coat after that, but it’s been worth every penny. Brooks Brothers factory store, 60% off, still cost more than I wanted to spend but it actually keeps me warm AND doesn’t make me look like I raided my dad’s closet.
What nobody tells you about layering is that the transitions between pieces matter just as much as the individual items. You can’t just throw random stuff together and expect it to work. Necklines need to make sense – crew neck over crew neck looks weird and bunches up. Colors need to work together because you’ll inevitably need to take something off during the day. I learned this the hard way when I wore a bright red sweater under a navy cardigan under a gray jacket, then had to take off the cardigan in a meeting and suddenly looked like a walking flag.
My current system is pretty simple but it works. Base layer is always merino wool in either navy, gray, or white depending on what’s going over it. Mid-layer is usually a cardigan, light sweater, or what I call a “shirt jacket” – those heavier button-ups that aren’t quite shirts but aren’t quite jackets either. Got a couple good ones from Taylor Stitch and Universal Works that I basically live in during spring and fall. Outer layer depends on weather but it’s usually either that wool coat for winter or a light jacket for everything else.
The key insight I had was that layering isn’t really about the clothes – it’s about having a system that lets you adapt to whatever the day throws at you. Some mornings I leave the apartment in three layers and come home in one because the weather changed or I spent the day in an overheated office building. The goal is being comfortable and appropriately dressed no matter what happens, not looking like you’re prepared for a polar expedition.
I’ve also learned that quality matters more than quantity. Three well-made pieces that work together beat five cheap ones that don’t. That expensive wool coat was painful to buy but it’s been perfect for three winters now. Those merino base layers cost more upfront but they last longer and work better than anything I used to wear. My friend Dave calls it “cost per wear” – if you use something all the time, spending more money upfront usually works out to be cheaper in the long run.
The other thing is that layering gives you options, which makes getting dressed way less stressful. Instead of having to guess what the weather’s going to do or what temperature some restaurant is going to keep their dining room, I can just adjust throughout the day. Meeting gets moved from the office to outside? Take off the blazer, keep the cardigan. Office air conditioning goes crazy? Add the light sweater I keep in my desk drawer. It’s like having a wardrobe that adapts to your life instead of the other way around.
I still mess it up sometimes. Last month I completely misjudged a day and ended up carrying around a heavy sweater for eight hours because it turned out to be way warmer than expected. But overall, figuring out layering has made such a difference in both how I look and how comfortable I am day-to-day. It’s one of those skills that seems complicated but once you get the basics down, it becomes second nature.
The funny thing is that good layering should look effortless, like you just threw on whatever was handy and happened to nail it. But really it takes practice and attention to detail. You need to understand how different fabrics work together, what colors complement each other, which pieces can be easily removed or added. It’s kind of like learning to cook – the end result should seem simple, but there’s actually a lot of technique underneath.
Now when I see guys struggling with this stuff – showing up to outdoor events in just a t-shirt when it’s clearly going to get cold later, or sweating through heavy sweaters when it’s obviously going to warm up – I want to help them figure it out. Not in a know-it-all way, because I definitely don’t have it all figured out yet, but because I remember how frustrating it was to constantly be uncomfortable because I didn’t understand something that seemed so basic to everyone else. Proper layering really is a game-changer once you get the hang of it.
Jacob’s a Chicago marketing guy still figuring out his look one outfit at a time. His writing is honest, funny, and self-aware—sharing the hits, misses, and lessons learned while building an adult wardrobe that actually feels like him.
