How to Layer Up This Winter

By: Peter Nguyen
Last Updated: December 8, 2020

Today’s question comes from Andrew:

“Any tips on layering up in the colder months?”

Two mistakes I see men make when it comes to winter layering:

  1. PACKING ON BULKY LAYERS Which makes for uncomfortable outfits
  2. GOING TOO TECHNICAL Unless your morning meeting is on the side of a snowy mountain, you don’t need a North Face jacket and a thermal beanie.

If you’ve been following my buying guides, you probably have everything you need to set you up for perfect office appropriate winter layering.

But in case you haven’t, here’s a small list of layering essentials:

Winter clothes to layer with for men

The Basics

  • Basic T-shirts (Crew or V-neck)
  • Winter weight button-down shirts (flannel or wool, like this from Uniqlo or this from Bonobos)
  • Knit sweater in merino wool or cashmere (like these from Bonobos or Mr. P)
  • Packable Down Puffer (jacket or vest, my personal favorites are from Uniqlo)
  • Jacket (such as a sportscoat, harrington, or even a leather jacket)
  • Topcoat (wool, cashmere, or a blend, like this one from Bonobos)

Bonus items

These items aren’t necessary for basic outfit layering combos I’ll be sharing, but are nice additions.

You can get pretty far when the basics listed above. Of course, there are the core winter accessories like beanies, gloves, and scarves you can add on at your discretion.

I would also recommend looking into lined pants like Bonobos flannel lined chinos, which gives you built-in insulation.

Just keep in mind lining pants adds to the thickness, so you might need to pick up a different size or cut depending on the fit.

4 formulas for layering outfits in the winter

Many of my private clients get tripped up when it comes to thinking about pieces, colors, combinations. But layering stylish outfits that keep you warm don’t need to be complicated.

My recommendation is to stick to mostly neutrals colors, then focus on the basic layering recipes below.

If you want to mix it up and add a bit of depth, use the swap trick and change the color of ONE item.

You don’t need to overdo it. The layers itself are enough to make your outfits stand out.

When it’s not so bad outside


Winter layering tips for men

If you’ve picked up a proper winter weight button-down and pants, you’re probably not going to need to pile much more on.

Esquire shares this great Ryan Reynolds style hack that I do all the time: wearing a topcoat as a jacket. As the name implies, a topcoat is meant to go over your jacket. But in this case, you’re wearing it in place of a jacket.

The only critique here is that if he decides to take off his coat, it might look a bit odd considering he’s sporting a tie. This is a great case to going tieless and wearing a shirt that’s a bit more casual. 

Alright, it’s pretty cold


How to layer three winter clothing items for men

I often get asked if one should go for a v-neck or crew neck sweater when wearing it over a collared shirt.

I prefer crewnecks, as a v-neck and collared shirt can go into terrible Dracula collar territory. 

When it comes to merino vs. cashmere sweaters, a few things to consider.

First the price difference. Nice merino can be as luxe and cost as much as a decent cashmere, but a nice cashmere can be a considerable investment. What you get in exchange is incredible softness and warmth (in all honesty, cashmere can even be too warm sometimes.)

Second is the itch factor. While some people find merino wools itchy, going for premium merino wool in a finer gauge will usually solve this. 

So which do I prefer? Cashmere all the way. 

Holy shit


How to layer winter clothes for men freezing

Most men wear puffers as standalone jackets, but a good packable puffer shows it’s full potential when used as a layering piece.

Not only does it add an insulating layer to your outfit, but also some surprising depth to your style without tons of bulk. 

You’ll be surprised how insulated this combo is.

Fuck, it’s freezing


When it’s so cold you’re cursing, it’s time to pull out the big guns. 


If you’re new to Heattech, here’s a quick primer:

Developed in conjunction with textile manufacturer Toray, Uniqlo’s Heattech is made from a proprietary blend of acrylic, cupro, nylon, polyester, and spandex that traps heat through their air pockets.

It’s essentially a blended, synthetic alternative to wool that feels more like cotton, making it ideal for thin base layers.

Heattech is the perfect solution to staying warm without adding a lot of bulk. 

I try to go as long as I can before needing to resort to adding a Heattech layer.

Throw on your beanie, scarf, gloves and some proper winter boots, and you’ll be good to go.

Need some clothing recommendations to layer up with?

Be sure to check out my Fall/Winter Capsule Wardrobe Guide

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