Hey Gents,

Effective layering is ridiculously important, especially as we get deeper and deeper into winter.

Ideally, you’d have a heavy-duty parka for the coldest temperatures and wind chills, but even if you’re just getting by with what you have, you can still stay relatively warm and dry.

Here are some clothes I grabbed from my closet. This is pretty typical of what I’d wear on a casual day in late autumn / early winter when running errands, meeting up with friends, or just hanging out.

layering example
(click to enlarge)

Thanks to a Lean Wardrobe, Layering Pieces Are Easily Swappable

The photo above is just a sampling of what I picked from my closet that day. You may not have these exact items, and even if you did, you may not be in the mood to wear them, or feel inclined to combine them in the way I did.

The good thing is, you can swap out lots of items for similar things in your wardrobe.

  • OCBD ↔ flannel
  • vest ↔ denim jacket ↔ sweater ↔ cardigan
  • leather boots ↔ bean boots ↔ lace-ups
  • beanie ↔ trapper ↔ wool fedora
  • cotton gloves ↔ leather gloves ↔ fur-lined gloves
  • M-65 field jacket ↔ wool pea coat ↔ puffer coat ↔ parka

If sweaters are more your thing than quilted vests, go with that. Raining outside, and you don’t want to ruin your new leather boots? Swap them out for Bean Boots instead. Prefer a more formal look? Go with a wool fedora over a beanie.

You get the idea.

A Few Basic Layering Tips


Start with the thinnest layers at the bottom, and wear the thickest layers furthest away from your skin.

So of course your underoos would be first, then a T-shirt or undershirt (if you wear those), followed by your button-up shirt (a thick cotton twill plaid, in my case) and denim, then any mid layers (quilted vest, as you can see above), accessories (such as scarf, glove, hat), then finally, your shoes and outerwear.

Easy on, easy off: Layers are great because you can peel them off one by one as you get warm, or add them as needed when the temperatures drop. Contrast that with wearing just a T-shirt + your heavy coat. I’ve been in situations where temperatures suddenly change and keeping a coat on would make me overheat, but a single layer wouldn’t be warm enough, either. Layers are key.

Bulkiness: Going from thinner to thicker layers helps to keep bulkiness down to a minimum. If you have too many bulky items (or thinner items over bulky items), it’s not easy to just peel off the layers you need to keep your temperature regulated.

Ease / Range of movement: Layering in this way helps with range of movement. Generally, your thick coat is tougher to maneuver in than your heavy cable-knit cardigan, which is tougher to maneuver in than your shirt, etc.

Insulation: Consider investing in long underwear or other garments that keep you insulated. For workouts, I use these Nike compression leggings which keep you warm, and if the need arises this winter, I won’t hesitate to wear these under my denim. Uniqlo has a line of undershirts and leggings called Heattech that I also plan on trying out, though I’m not much of an undershirt guy.

Know thyself. In the end, you know yourself best. I get warm fairly quickly, especially if I’m walking a lot (which you tend to do in NYC), so I may not wear as many layers as, say, my wife, who gets cold easily.

If you are always cold (and stay that way, despite the activities you’re participating in), then add the layers you need to stay comfortable. It may take some trial and error, and of course, will depend on the weather, but you’ll figure it out in no time.

Just remember, it’s better to over-layer; you can always take off a couple things if you start to overheat.

Got any layering tips?

I grew up in California and it never snows there, so this year, I’m experiencing my first real winter season as an adult.

Some of you may be more experienced than me in layering, especially for the extremely cold days when wind chills bring temperatures below 0 degrees. I’d love to hear from you guys in the comments!

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18 Responses

  1. Nordlund63 on

    You’re going to have to grab something heavier than a field jacket once it starts getting really cold. Probably a parka or a pea coat.

    • Barron on

      Yeah, I do have a pea coat which is my cold weather default, but based on my experience so far, thinking about investing in a snorkel parka or something else that will help cover the head / neck /face better.

  2. Carl on

    Great article. For many years I worked in the outdoors in New England, I found that socks are key to staying warm over several hours. If your feet are cold it is very difficult to warm them up, so a good pair of wool socks is possibly the single best thing you can wear to combat the low temperature. Wool still insulates when wet where cotton will chill you to the bone.

  3. Patrick on

    Uniqlo’s HeatTech is great, not only because it holds in heat (which it does…just not all that much, but still better than none at all), but because it doesn’t absorb moisture and get cold. This is the main reason why I wear them. The HeatTech socks are a cheaper, still-dress-clothes appropriate alternative to heavier weight wool dress socks. The Airism stuff is nice too.
    Also, if this is about layering to keep warm, there is a real lack of wool on here. Cotton is nice and all, but it’s a poor insulator when dry. Throw some moisture in the mix and it’s beyond useless…it will make you colder.

    • Barron on

      Yeah good point. Certainly keeping away from cotton as a base layer, and you’re right, should’ve highlighted the awesomeness of wool more (sweaters, pea coat, socks, etc.)

  4. Bo on

    Found this article extremely timely, as I had to layer up today in NYC! For work, I’m wearing a dark denim shirt, grey v-neck sweater, tan chinos, brown suede chukkas and a charcoal blazer, but for the commute, I switched layers up — I have a lightweight military jacket that I threw on under my Uniqlo wool blend blazer (the blazer’s just long enough to cover the jacket), along with a scarf under the military jacket. I also have a waxed cotton chore coat from Gustin that I’m planning to wear over a denim jacket this weekend — all based on suggestions above!

  5. Oldnag on

    Long underwear, or long johns as we call them here in SK. You can’t see them under your pants so they don’t have to be pretty. We always focus on layering our upper bodies and forget that we’re just putting one layer on our poor legs. I am guilty of this too. If we can keep our bodies from exhausting energy trying to keep our legs warm it will be able to focus those energies elsewhere.

    • Barron on

      Heh, I’ve experienced that recently (only having one layer to cover legs) and it’s no fun. Definitely investing in a pair of long johns!

  6. Bobby Donohue on

    I am usually guilty of the coat over a t-shirt thing. Thanks for writing this, sometimes the most “obvious” solutions elude me. I have a vest, and a jacket, but I hadn’t thought to layer them like this. I would just wear my heavier, bulkier coat, which I don’t really like as much. Now I can wear my stylish (less warm and bulky) coat with the vest under it, and be warm. Thanks!

  7. Adam on

    Wool socks are a better choice when temperatures really plunge. They let your feet breathe more and hold in the heat better. I have a great old pair of thick wool socks that I will wear under my Blundstones or work boots when dealing with chilly Winnipeg winters.
    Also, avoid cotton as a base layer, especially if you are expecting to work up a sweat.

  8. Khishaan Navaretna on

    I love my Uniqlo heat tech. It is thin, retains warmth and yet not too hot when you are indoors where you have no control of the heating. With them, I am sufficiently warm (I could stay out with just them and a dress shirt on top), and yet not too warm that it is uncomfortable indoors. Works perfect to smooth out those extra flabs too 😉 Speaking of Uniqlo, they also have wind proof jeans, which negates the need for long johns. Although I personally have not used them and prefer thicker but breathable pants instead.

  9. -B on

    A bit weird seeing so much winter fashion advice when I’m trying to cope with the hot Australian sun this time of year! Some great info here regardless, love your work man.

    Just a quick question while I’m here.
    I’m wanting to splash out a bit on my first quality blazer for New Years this year. It seems most fashionistos (real word?), including yourself, seem to have the consensus that a navy blazer is the most splurgeworthy of the coats and jackets.

    Seeing it’s pretty toasty here at the moment… and I already have a dark navy pair of slacks and jeans – I was thinking of getting a blazer in baby blue or white & navy striped seersucker. My question is: would I be better off getting the navy blazer “staple” down before I throw a few hundy at something I apparently might not get as much utility from?

    • Barron on

      I actually have a navy and white striped cotton blazer that I love wearing in the summer. It gets a lot of use (at least in my wardrobe). Since it’s summer where you are, wouldn’t hurt to get one in seersucker if you know you’ll use it now and in the future.

      I also have an unlined, unstructured cotton / linen sport coat in navy which I use more than my navy / white stripe, so there’s always that option as well.