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How to Wear Layers: 4 Rules and 19 Outfit Ideas for Men

How to Wear Layers: 4 Rules and 19 Outfit Ideas for Men

How to wear layers

How do you wear layers when it's cold outside? Are there any "rules" that you should follow when layering up?

If you've asked yourself these questions, or you just want some example outfit ideas, you're in the right place. This guide will help you layer up in comfort and style as the weather starts to cool down.

Why wear layers?

Just like making sure your clothes fit properly, wearing layers is one of those secret weapons every stylish man has in his arsenal.

Simply put, layers look really cool. They add depth, texture, variety and visual interest to otherwise plain outfits.

Vest on and off

Look at any GQ photoshoot or runway show at New York Fashion Week, and you'll see that most of the models are wearing layers.

Similarly, check out any red carpet event where celebrities have paid big bucks for personal stylists to make sure they look great. Guess what these people are wearing?

You guessed it: layers.

In fact, we'd go so far as to say that wearing layers is one of the easiest ways to improve your personal style (right after wearing clothes that fit well).

But there's a downside to layering up: it can be confusing. And lots of guys are wearing layers the wrong way.

Fear not! The next section will give you all the info you need to become a stylish layering ninja.

4 Layering "Rules" for Guys

Like most things in fashion, there are some guidelines you can follow when it comes to wearing multiple layers. We call these "rules" but you can think of them as best practices (since they can be broken).

Layering rules for men

You don't have to follow these best practices all the time, but it's important to understand them when you're putting together a layered look.

Rule #1: Thin Inside, Thick Outside

In general, you want to wear lighter/thinner fabrics closer to your body, and heavier/thicker fabrics farther out.

For example, you might wear a woven cotton button down shirt under a merino wool sweater, then throw on a thick wool-cashmere topcoat to, well, top off your getup (see what we did there?).

Here's another example:

Henley Shirt > Quilted Vest > Field Jacket

Layering example

The shirt is very lightweight, while the vest is made from thicker, sturdier material. The jacket is the thickest, heaviest garment in this outfit, and it's worn farthest from the body.

This rule is pretty obvious and usually happens naturally. For instance, you'd never wear a thick wool sweater under a cotton dress shirt, right?

Right. Let's move on...

Rule #2: Three Layers Max

When it comes to layering, three is sort of the magic number. Any more than that is usually overkill, and it can create a bulky, overstuffed look.

Plus, if you wear too many layers, you may overheat and lose mobility.

Just remember: 2 is great, 3 is perfect, 4 is overkill.

Rule #3: Light Inside, Dark Outside

Most layered outfits consist of multiple colors. How do you combine different colors for a cool layered look? You can't go wrong with this formula:

Wear lighter colors closer to your body, and wear darker colors farther from your body (outer layers).

Here's an example:

White Dress Shirt > Grey SuitCharcoal Topcoat

Keep in mind, this is a loose guideline and can absolutely be ignored. For example, you can definitely wear lighter colored top layers over darker outfits, such as a camel topcoat over a navy suit.

But, if in doubt, you can't go wrong following this principle, especially if you keep the next rule in mind.

Rule #4: Each Layer Works

Here's the final "rule" of layering: make sure each layer works okay on its own.

Jacket on and off

If you're like us, you probably have a section of your closet reserved for those shirts that you can only wear under sweaters. Maybe the sleeves are too long, or they're just too baggy through the torso.

Most likely, you bought these shirts before you discovered Peter Manning NYC ;)

The problem is, what if you need to take off your sweater? What if you get too hot or someone spills their drink on you?

You should always make sure each layer can be worn on its own. This means it needs to fit well and go with the rest of your outfit.

If you follow this guideline, you'll never be caught off guard.

19 Layering Outfit Ideas

Now that we understand the basic guidelines for putting together a nice layered look, it's time to put this stuff into practice.

Here are some layered outfit ideas you can use for inspiration, or just steal for yourself (no judgement here). In no particular order...

Outfit #1: Henley Shirt and Vest

Here's a simple, casual layered look featuring a henley shirt and lightweight quilted vest.

Vest henley cords

This outfit is perfect for days when it's not quite cold enough for a jacket.

Outfit #2: Add a Jacket

Of course, you can add a jacket to this vest/henley combo for extra warmth.

Field jacket over vest

Something light-medium weight, such as a field jacket, works really well over a quilted vest.

Outfit #3: The Quarter Zip

A classic business casual combo, the quarter zip sweater layers perfectly over a button down shirt.

Quarter zip sweater

Wear this with jeans, chinos, dress pants or in this case, slim fit corduroys.

Outfit #4: Add a Blazer

You can also wear the quarter zip sweater under a navy blazer for a slightly dressier look.

Business casual layers

This outfit transitions from the office to date night with ease.

Outfit #5: Henley Shirt and Field Jacket

For those early fall days, you might just need one extra layer, such as our Tribeca Field Jacket.

Field jacket over henley

Field jackets are really versatile, and they look especially nice with more casual tops (in this case, a long sleeve henley shirt).

Outfit #6: Leather Jacket Layers

This outfit is a tasteful blend of rugged and refined. The lambskin leather jacket wears nicely over a wool crew neck sweater and button up shirt.

Fall layers

Dress things down by wearing jeans instead of chinos or dress pants.

Outfit #7: Leather and Flannel

Speaking of leather jackets, they also go perfectly with flannel shirts.

Leather jacket with button up shirt

This brown leather jacket looks great with an untucked flannel button up and slim fit indigo jeans.

Outfit #8: Field Jacket Layers

Here's a different take on the field jacket. This navy version is worn over a quarter zip wool sweater and denim shirt.

Navy field jacket

The olive chinos add a bit of refinement to this getup, and the dress work boots anchor everything down in a rugged, modern way.

Outfit #9: The V-Neck Sweater

V-neck wool sweaters tend to be more dressy than cotton quarter zips, and they look great worn over Oxford shirts.

Topcoat layers

The black topcoat and black slim fit jeans look great together. Don't be afraid to wear your topcoats with more casual pants!

Outfit #10: Casual Layered Topcoat

Speaking of wearing topcoats casually, this navy topcoat looks amazing worn over a light grey hoodie and white t-shirt.

Topcoat over hoodie

The light wash jeans add to this outfit's casual vibe, which makes the topcoat a really cool choice.

Outfit #11: Field Jacket and Vest

Olive is one of the best colors for field jackets. It works really well with pretty much any shade of blue.

Field jacket over vest

Again, the lightweight vest adds a bit of warmth, texture, color and visual interest to this simple outfit.

Outfit #12: Crew Neck and Oxford

Your wool sweaters can be worn casually too, especially the crew neck variety.

Casual fall layers

This is a comfy, low contrast outfit that's perfect for casual Fridays at the office and lazy Sunday afternoons at home.

Feel free to leave it untucked for a more casual look.

Outfit #13: Harrington Layers

While it looks stylish worn on its own, the Harrington jacket is also great for layering.

Harrington layers

Here, it's worn over a crew neck sweater and white button down with slim fit khaki chinos - a timeless combo that will never go out of style.

Outfit #14: Raincoat and Flannel

Similarly, the raincoat is also a nice layering piece that can be dressed up or down.

Raincoat over work shirt

Wear it over a flannel shirt and henley for a casual look that's ready for cool temps and unpredictable weather.

Outfit #15: Lightweight Vest and Sweater

When you need to layer up for warmth but don't want to carry around a jacket all day (or night), wear a light vest as your outermost layer.

Quilted vest over sweater

Our Flatiron Vest looks right at home over a crew neck sweater and white button down shirt, paired with slim fit dark wash jeans on bottom.

Outfit #16: Vest, Flannel and Henley

For a more casual look, you can keep the vest but swap the sweater and button up for a flannel shirt and henley.

Flannel shirt layers


Finish this layered look off with a baseball cap and your favorite sneakers, and you're ready the weekend.

Outfit #17: The Cotton Pullover

For something more casual than a wool sweater, try a cotton pullover worn over a crew neck t-shirt (when in doubt, go with solid white).

Field jacket over brown pullover

This brown pullover looks great with a navy field jacket and khaki chinos.

Outfit #18: Field Jacket and Cardigan

The cardigan is a stylish alternative to the v-neck sweater, as it adds a little bit of dressy flair to your look.

Field jacket over cardigan


Here, the blue microcheck shirt goes perfectly with the dark green wool cardigan, setting the foundation for the tan field jacket to pop.

Outfit #19: Leather and Denim

If you're more of a leather jacket guy, try wearing one over a denim shirt and cotton pullover.

Leather jacket layers


It's a smart casual combo that's perfect for a variety of situations, and you can totally change the vibe just by changing the pants and shoes.

How do you layer?

We hope this post gave you some new ideas for layering up this fall and winter. If you need some great layering pieces to add to your wardrobe, check out some of our favorites:

Flatiron Vest | Wool Crew Neck Sweater | Wool V-Neck Sweater

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