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!

Got a question? Hit me up!

Comments are old school, though. Why not tweet at me or DM me on Instagram?