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 that 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 what if you want to look good during your morning slog through the slush?

This article gives up the secret to staying warm and looking great all season long.

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.

Four Most Important Tips for Wearing Layers

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.

#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.

#2: No More Than Three

Two is good; three is great; four is too much.

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

#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.

#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 outfits.

The 3 Layering Essentials

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

Item #1: The 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.

Item #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

Brock tried on a huge selection of Uniqlo items and really liked the sweaters.

These are fairly slim, so while they work for us shorter guys, the sweaters only really work if you’re on the skinnier side.

Item #3: Jackets and Overcoats

Last, but not least – your outermost layer.

This will be what people see first, so buy quality, whatever you choose.

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

You’ll see Brock wearing casual medium weight jackets (like field jackets and leather jackets) all the time.

These are great three season choices for everyday outerwear, and they’re perfect for layering.

16 Great Ways to Layer Your Outfits

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

Two-Layer Looks

Sticking with two layers is minimal, stylish and perfect for mild temperatures.

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

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

Here we’ve paired a simple oxford 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.

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

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

Uniqlo does a great job nailing this preppy style.

Idea #4: A Henley Shirt with a Field Jacket

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

It looks great dressed down, as in this example, but it can be dressed up, 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 above, and wear with indigo skinny jeans.

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 pairs well 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 Brooks Brothers only make quality.

Three Layer Looks

Ready for the big leagues?

Just one additional layer creates tons of new opportunities, many of which work even in temperate autumn weather.

Idea #7: A Crew Neck Sweater, Vest, and Leather Jacket

Feel free to go with a pop of color for the sweater underneath – a pattern would also be great.

This look works because of the textured layering. No two textures are the same.

Having a go-to leather jacket like this really broadens what you can do with your fall and winter wardrobe.

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

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, A Cotton Pullover, and a Leather Jacket

It’s hard not to feel like The Terminator when wearing a leather jacket. That’s precisely why you need one.

You can soften the look with a merino crew neck sweater, as seen above.

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 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 last year 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 a dark chino for something dressier, or choose jeans for a more casual look.

Idea #15: A Button Down, a Cardigan, and a Leather Jacket

We included this one to showcase the versatility of a great leather jacket.

Switch the denim button down for a textured shirt and the cotton crew neck sweater for a wool cardigan. Now you’re layering multiple colors, weights, and textures. This is advanced stuff.

Bonus points if you choose shades of the same color for all your layers.

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

These last two ideas revolve around great quality, dark top-coat.

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

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

This bonus look demonstrates how a look that you might not have thought about can really work.

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.

Conclusion

Now you’re ready to start layering looks and looking great while staying warm through fall and winter.

Bust out the sweaters and vests.

It’s that time of year when we burn our mouth with boiling hot chocolate. It’s layering time.