How to: Layer up! Easily and effectively

by   |  in Smart Casual

Hey gents,

Right now, in some parts of the world, it’s cold.

Like freezing balls, I-don’t-want-to-leave-this-blanket-much-less-my-house cold.

In other places, it’s just a bit chilly, like here in San Francisco right now.

If you’re not among the (whom I consider) lucky crowd that experiences balmy summer-like weather all year long, you’re probably in the same boat as I am… if not worse.

In the dead of winter, you should prepare thoroughly before you leave the house. Rarely should you walk out with just a shirt and a coat.

One, because you should probably put on pants. But also, two layers for your upper torso simply doesn’t cut it.

Temperatures change from place to place, and you don’t want to leave yourself with only two choices: coat on or coat off. It sucks when temperatures outside are below freezing, but indoors at your destination, it’s REALLY warm because the heater is pumping.

Why’s it so tough?

A few days ago I asked EG readers on Facebook what some of their hang ups were when it came to layering. Here are a few:

Pretty good with colors and “matching.” I have more of a hard time with fabric and styles. – Joshua

The constant heat all year round in miami. – Carlos

Hard to pull off when the layers begin restricting movement under the arms and across the back… – Scott

I understand your concerns, but take solace in the fact that layering is still achievable despite your many worries.

Yes, there’s even a way to layer effectively for those in warmer climes. This article is focusing on cold weather layering, but don’t worry, we’ll get to you in a separate article.

Regardless, you can use some of these morsels of advice and apply them to your situation (using lighter fabrics, of course.)

First off, some benefits to layering

I can’t suggest you do something without first explaining why it’s a good idea, right?

Easy to get warmer or cooler as needed

Effective layering makes it easy to maintain your desired temperature. Too hot? Peel off the topmost layer. Getting cold? Simply start adding your layers back on.

Adds more interest to your outfit

When you have more items on your body, the more you get to experiment with looks as you combine different colors, patterns, and textures.

Take a look at any menswear store’s window displays or dress forms during the fall or winter, and you’ll see some great examples.

It can help you achieve the high / low look

We’ve discussed this idea of high / low before, remember? Doing so will help you make use of all the clothes in your closet, plus it adds visual interest and balance to whatever you’re wearing.

Effective layering helps you with this simply by having more pieces on your body to work with.

The BIG Question: How to layer

Let’s start with some general pointers about layering.

The lighter and thinner the layer, the closer to your body

This might be common sense, but in case it isn’t, the lighter and thinner the layer, the closer it should be to your skin. Doing so will help ease restriction, and it also prevents you from having to take all your clothes off if your innermost layer is super thick and causing you to overheat.

Colors should complement each other

I always refer back to this article because the ladies pictured here have their ish together. You’ll see that they’ve pulled off layering perfectly, but not only that, they understand how to put together colors that complement each other (not match… complement).

This idea of complementing could be an article all its own, but for now, try to get a feel of what looks good together.

vintage RL swatches

For some visualization, check out the web app Kuler. There are plenty of color combos to feast your eyes on, for example, this one.

If you explore further by clicking on the little button that looks like an equalizer, choose a base color, then click on the different rules (Analogous, Triad, Complementary, etc.), you’ll get an idea of how to pair colors.

Stick to one bright pop of color

To add to the color conversation, make sure you choose at most one bright pop of color. You already have a lot going on with individual layers, and you don’t want two, three, or more bold colors. They’ll all end up competing with each other.


You want the items in your ensemble to have a lot of contrast. Pair your lights with your darks. Don’t go all light, or all dark, or all muted, or all washed out. More on this further down… just keep reading.

Patterns: a reader suggestion

Remember to have “deeper” patterns father out. So have a smooth shirt, lightly textured jacket, and then heavily textured overcoat. Simple and it works. –William

I like this idea, and it makes sense. Try it out and see how it works for you.

How to layer: A visual explanation

The best way to explain “how” is through pictures. Our friends at Onassis were gracious enough to let us style and shoot some outfits at their San Francisco location to help illustrate layering.

As we were doing this, I was super excited to see the fit of all these pieces and how well they seem to go together.

Anyway, I digress. On to the examples (click images to view full size):

Layering example #1

outfit 1

Here’s an example of that high / low look in regards to the dressiness of each individual piece. This would be a great choice when going about your day, or even for work (if your office has a casual dress policy).

Starting off with a basic light-colored chino and pencil stripe dress shirt, add a silk tie (dressy), a rugby shirt for warmth (casual), and finish it off with a close-fitting wool top coat (dressy).

outfit 1 frontRegarding pattern: Don’t be afraid to mix stripes. The bold stripe pattern of the rugby works well with the thin pencil stripe of the shirt. The tie has its own subtle pattern as well. Everything else is relatively muted.

Shoe suggestions

(side note: all shoe suggestions are affiliate links. If you happen to purchase one, you’re supporting this site in a very small way, which I appreciate. If you don’t want to use these links, you can easily do a search on Google or Zappos to find the shoes.)

Depending on weather, you can do a loafer, lace-up, or rugged, weather-appropriate boots.

Layering example #2

outfit 2

Another take on high / low. What really dresses this up is the wool sport coat. Everything else is more casual. Good example of how one thing (in this case, a sport coat) can really elevate an outfit.

The quilted vest adds that additional layer of warmth (not to mention visual interest) which could potentially make you leave that coat at home. Of course, if it’s freezing outside, bring the coat anyway.

Regarding colors: Notice the one bright pop of color, the mustard pants. Every other piece grounds that color by remaining neutral, muted. The nice thing is, even up close, you can see subtle textures and shades of color that work well together.

Regarding pattern: Subtle stripe on the jacket, quilted pattern on the vest, plaid shirt. Subtlety is key.

Shoe Suggestions

Layering example #3

This one is pretty straight-forward. Throw on a v-neck under a flannel shirt, add a middle layer (in this case, a shawl collar knit vest, though a cardigan would also work), and a substantial leather jacket. Dark denim on your bottom half.

outfit 3 frontRegarding colors: Again, notice there’s one bright pop of color (the red check flannel).

Regarding fabric thickness: To minimize bulk, you have to make sure each item works well together. The sweater (or vest) should be loose enough to fit a flannel comfortably underneath, but obviously not so large that you could fit a litter of puppies in there.

Shoe Suggestions

Layering example #4

outfit 4

This example utilizes that pop of color well, but this time, it’s in the outerwear. Starting with a light blue striped shirt and brown cords, add a warm V-neck sweater and finish off with the flight jacket and beanie.

Regarding colors: Hopefully you’re seeing the trend here. Notice the one bright pop of color is the jacket, everything else is muted / earth tones. Even the beanie, though it has color, isn’t too bright or attention grabbing.

Regarding contrast: If you focus specifically on the cords and the sweater, you’ll notice that even though they both have brown tones, one is really dark like a cigar wrapper, and one is light like oatmeal. That’s contrast. Do more of that.

And then in the middle of it all, it’s broken up by that subtle injection of color from the blue and white stripes. Browns play really well with light blue. Keep that in mind.

Shoe Suggestions

Some of your concerns

I hear ya. Even after I’ve shown you some visuals, you may still be a bit skeptical that you can pull it off.

Well, I believe in you! (Does that help?)

Here are some concerns you’ve voiced (via Facebook):

“Too damn hot!”

Whoaaa. Take it easy there, Sparky. No need to yell.

You know your body best. If you tend to overheat easily, then wear one less layer. Maybe all your layers need to lighten up a little.

Maybe you can do without a heavy coat if you’re wearing a vest, sweater, and sport shirt. Maybe you need to lose the vest. Maybe that day, you just shouldn’t have layered too much because you’re super worked up and getting extra sweaty.

As with everything new, it’s all trial and error. Figure out what works best for you.

Lack of mobility

randy snowsuit

Are you wearing one too many layers?

Again, it comes down to trusting yourself. If you feel restricted, maybe the particular combo you chose shouldn’t be layered together.

Or maybe you’re simply not used to it.

Give it a chance and as long as you can carry on with your day, it will be something you eventually get used to.

It could be your sweater is too thick, or your shirt isn’t slim enough and is causing excess fabric to gather and feel uncomfortable.

Maybe your uppermost layers aren’t as flexible, large, or forgiving.

Hey, it happens. Try again, my friend.

I live in a place where it’s hot year-round. How can I layer effectively?

To be honest, layering may not always make total sense depending on where you live. If you live in a desert or a tropical country, for example, it’s not always easy to dress comfortably, much less dress stylishly.

But! It can be done. The trick is to use less layers, and to make those layers weather-appropriate.

Let’s say you live in Miami. Tropical climate, relatively hot and humid most of the year.

You’ll obviously use less wools and tweeds as, say, someone in New York in the winter. But you still have plenty of lightweight fabrics to layer with: lightweight cotton, cotton cashmere blends, linen, cotton linen blends, chambray.

You’ll also be using less pieces to layer.

Most people walk around with as little as a t-shirt and shorts in hot weather areas. Do you know how far you can set yourself apart simply by throwing on a linen sportcoat? Or a cotton suit? Or lightweight chinos and a polo shirt?

Assuming you’ve mastered the correct fit for your body, simple changes to your daily outfit will make a huge difference.

Also, if the weather changes at night or if it can be chilly in the early morning, there’s your opportunity to throw on a lightweight sweater as your uppermost layer. Simple, but effective.

In conclusion

I hope this helps in your quest to layer a bit more effectively. It can be done well, no matter where you live.

Thanks again to our friends at Onassis. Look forward to other collaborative pieces with these guys, and in the meantime, check out their goods.

Questions? High fives? Leave em below.