How to Wear Layers During Fall and Winter + 16 Outfit Ideas

Wondering how to wear layers during fall and winter? Look no further. These layering rules and outfit ideas will help.

Ready for another polar vortex? Of course not. No one ever is. When you’re looking for clothes this season, shopping for the heaviest jacket you can find may not be a bad idea.

But a heavy duty parka is often overkill, and simply layering up can offer enough warmth without all the bulk.

This article gives up the secret to staying warm and looking great during fall and winter by wearing layers.

Keep reading to learn everything you need to know about layering up.

Why Wear Layers?

Layers are the secret weapon in every man’s wardrobe because they add variety, depth and texture to outfits.

Also, it’s easy. You can take two or three pieces that are somewhat plain on their own and create a visually interesting ensemble.

Plus, layers are comfortable. It’s easy to add or remove a layer, as needed, to adjust your temperature throughout the day as your environment changes.

The 4 Rules of Layering

Rather than “rules” – which are made to be broken – consider the following shortlist of best practices to consider when putting together a layered outfit.

Bend or disregard them as you see fit, but at least understand the rationale behind them.

Know the rules, then break them 😉

Rule #1: Each Layer Should Work on its Own

This is foundational in building layered outfits from the undershirt out.

You thought you could get away with wearing that weird elf shirt your ex-girlfriend’s mom got you three years ago, didn’t you?

Well, what happens when you dump your coffee right smack in the middle of your nice sweater? Now you’re stuck wearing just that silly shirt for the rest of the party.

Make sure you’re wearing something you’re proud of underneath. Think of Murphy’s Law. Anything that can go wrong, will go wrong.

Rule #2: No More Than Three Layers

Two is good; three is great; four is usually too much (not always).

Too many layers and you risk flaunting a bulky, padded look. Stick to three layers maximum and you’ll be in good shape.

Rule #3: Thin on the Inside, Thick on the Outside

By this point, you’ve chosen three pieces that work well independently and you want to create a layered look.

But before you dress, consider how practical each piece will be when layered together.

For example, if you throw on your favorite heavy cashmere sweater on before a light jacket, you may soon discover that the jacket is overkill. You don’t want to end up carrying it around all day to avoid overheating.

If that’s the case, keep the sweater, but reach for something thinner to layer underneath.

If you wear lighter and thinner fabric closer to your body and heavier pieces further out, you’ll be ready for any kind of weather.

Note: this principle usually happens naturally, so don’t overthink it!

Rule #4: Dark on the Outside, Light on the Inside

There is nothing more classic than starting with a light shirt and going darker with each additional layer.

When in doubt, always go classic with a formula like this one: wear lighter colors closer to your body and wear darker colors as your outer layers.

Easy enough, right?

But all these tips are about how you should layer as opposed to what you should use as layers.

Here is a list of what to look for in each layer to create dynamic, functional and stylish outfits as the weather cools down.

3 Layering Essentials

While it’s fun to get creative with your layers, there are a few best practices to keep in mind.

Let’s look at each layer in more detail, starting close to the body and working our way out.

Layer #1: Shirts

In addition to your fitted dress shirts and t-shirts, consider adding one or more of the following:

• A Flannel Shirt
• An Oxford Shirt
• A Denim Shirt
• A Henley Shirt

Stores like J. Crew will have a great selection of base layers to try out. They make solid clothing and we like them because there’s a good chance you’re within an hour’s drive of a store.

It’s a good place to start, especially if you want to test some of these layering looks before you invest your hard-earned dough.

Layer #2: Vests and Sweaters

You’ll get mileage with any one of the following, but shoot for two or more to avoid getting into a rut.

• A Medium or Dark Color Vest
• A Quarter-Zip
• A Crewneck Sweater
• A V-Neck Sweater
• A Hooded Sweatshirt
• A Cardigan Sweater

Sweaters are easy to pull off. A cotton crew neck or wool v-neck will get plenty of wear during fall and winter.

But, if you haven’t tried one yet, consider a lightweight vest. These make excellent middle and outer layers.

Layer #3: Jackets and Overcoats

Last but not least, your outermost layer. This will be what people see first, so buy the highest quality you can afford (don’t go into credit card debt for a parka).

• A Field Jacket
• A Leather Jacket
• A Blazer/Sportcoat
• A Raincoat
• A Top Coat
• A Parka

I really like casual medium weight jackets like field jackets and leather jackets. Bombers and Harringtons works well too.

Wool topcoats are underrated. These can be worn casually or dressed up, unlike parkas (which are decidedly casual).

18 Stylish Ways to Wear Layers

As we suggested above, two layers are good and three layers are great. Let’s start with looks comprised of two layers and build from there.

Idea #1: A Button-down Shirt with a Vest

It’s simple, and it’s perfect for temperate autumn weather.

Here I’ve paired a simple button up shirt with the J.Crew Walker Vest.

Idea #2: A Button-Down Shirt with a Quarter-Zip

Here, the darker purple quarter-zip layers well on top of the lighter purple button-down shirt.

Wear this combo with dark navy chinos or corduroys and you’re good to go.

You can find killer quarter-zips at J. Crew, Mizzen + Main, and Banana Republic. If you’re a shorter guy, here’s where to buy sweaters for short men.

Idea #3: A Button Down with a Crew Neck Sweater

Dress it up or down by tucking or untucking the shirt.

Grey, white and light blue look great together. If you’re wearing light wash jeans, try leaving your button up untucked for a more laid back look.

Idea #4: A Henley Shirt with a Field Jacket

A high quality field jacket will be your best friend throughout autumn and early winter.

It looks great dressed down, as in this example, but it can be dressed up for a smart casual look too.

Idea #5: A Flannel Shirt with a Leather Jacket

With winter around the corner, if you choose only two layers, you’ll need each one to be substantial.

Consider an untucked flannel and brown leather jacket combination, as seen below, with slim dark blue jeans on bottom.

All Saints are known to do great work with their leather jackets and the same goes for ASOS on the budget side.

Idea #6: A Flannel with a Raincoat

Functional outerwear is a must in most places, so invest in a great raincoat. Paired with an untucked flannel, this combo looks nice with slim jeans.

Brooks Brothers makes a classic raincoat that has all the hallmarks of great British design but at a more affordable price.

Don’t get us wrong, it’s still an investment, but you’ll need a heavy coat every year, and a good one lasts decades.

Idea #7: A Quarter Zip Over a Button Up

This is a classic look, so if you’re not into somewhat safe, traditional style, it might be too plain for you.

I love this kind of outfit because it would have looked good 50 years ago, and it’ll probably look okay 50 years from now.

Idea #8: A Henley Shirt, a Flannel Shirt and a Field Jacket

Here’s a more rustic look, perfect for a weekend away in the country.

The undone buttons in the shirt add some intrigue to an otherwise straight forward style.

Here we have a J. Crew Factory vest over a Tailor Store flannel.

Idea #9: A Button-Down, and a Cotton Pullover

You could throw a jacket on over this getup, but if it’s not that cold outside, this two-layer look is functional and stylish.

Leaving your bottom layer untucked creates a more casual, laid back vibe (especially when paired with sneakers).

Idea #10: A Button-Down Shirt, A Crew Neck Sweater and a Harrington Jacket

A Harrington Jacket is plenty interesting alone, but it adds a little something extra when combined with a crew neck sweater and a button-down shirt.

Here, you get the visual interest of another layer without all the bulk. Wear this combo with slim chinos to complete the look.

Idea #11: A Button Down, a Cardigan, and a Field Jacket

Cardigans are essentially v-neck sweaters with a little extra personality.

When worn under a khaki field jacket, a cardigan adds a unique classic look that other layers can’t supply.

Idea #12: A Denim Button Down, a Quarter Zip and a Field Jacket

Never underestimate pant color when it comes to assembling an outfit.

Here, the olive chinos complement the top layers to create a modern look.

If you don’t have any olive chinos in your wardrobe, we highly recommend trying some on!

Idea #13: A Flannel, Fleece and Vest

The key here is the contrasting texture of the vest. We featured this outfit a while back when fall was in full swing.

It’s a combo of a Tailor Store flannel, Uniqlo fleece, and J. Crew vest.

Idea #14: A Denim Button Down, a Crew Neck Sweater and a Leather Jacket

Dial this look up or down with the right pant color.

Choose dark wool flannel trousers for something dressier, or choose jeans for a more casual look.

Idea #15: A Three Piece Suit and a Topcoat

You can layer up in formal situations too. In fact, a three piece suit makes layering easy because all you need to do is throw on a coat.

This is one situation in which wearing four layers is totally appropriate (it won’t look too bulky).

Idea #16: An Oxford Shirt, a V-Neck Sweater and a Top Coat

These last two ideas revolve around a classic wool topcoat.

Choose a v-neck as your second layer if you’re looking for something dressier than a crew or quarter zip sweater.

Idea #17: A T-Shirt, a Hoodie and a Top Coat

Most guys think topcoats can only be worn formally, like with a suit and tie. The truth is, you can dress them down too!

Part of this outfit’s success is thanks to the four best practices we outlined above: start with great quality, well-fitted layers, choose only three of them, then layer them from thinnest to heaviest and from lightest to darkest.

The result? Your “dressy” navy topcoat pulls double duty in this fresh, casual getup.

Idea #18: A Hoodie Under a Denim Jacket

Here’s a casual, almost streetwear look that combines two classic casual staples: the hoodie and the denim jacket.

Because the hoodie, t-shirt and denim jacket are neutral colors, you could black, dark or light blue jeans with these top layers, and pretty much any type of sneaker or boot would look good.

Questions About Layering

Here are answers to the most frequently asked questions about wearing layers:

How can I wear layers without looking bulky?

Try to avoid bulky puffer jackets. Opt instead for thinner outerwear, like wool topcoats. Avoid wearing more than three layers. For more tips, reach our guide to outerwear for shorter men.

How do men wear layers?

Men can wear layers by following the layering “rules” in the above guide. Specifically: don’t wear more than three layers, wear darker colors on the outside, wear thinner fabrics on the inside, and make sure each layer looks good on its own.

How many layers should you wear in winter?

You should wear as many layers as it takes to be warm and comfy, but three layers is the sweet spot. Any more than that, and you risk looking too bulky.

How can men wear layers during summer?

Oftentimes, it’s simply too hot to wear layers during summer. But you can wear one outer layer if it’s made from thin, breathable fabric (think linen, hopsack or chambray). A lightweight cardigan, cotton/linen chore jacket or lightweight windbreaker are all good choices.