• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

The Modest Man

  • .
  • Start Here
  • Blog
  • About
  • Outfit Ideas
  • Free Stuff
Home / Blog / Clothing and Style

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

Published on September 11, 2021 by Brock McGoff · Clothing and Style May contain affiliate links (what's this?)

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

Table of Contents

  • Why Wear Layers?
  • The 4 Rules of Layering
  • 3 Layering Essentials
  • 18 Stylish Ways to Wear Layers
  • Questions About Layering

How to wear layers

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.

4 Rules of Layering Infographic

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.

J Crew Factory Walker Vest navy
If you wear a vest under a jacket, it should look good without the jacket on too.

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).

Khoi in NYC wearing smart casual outfit

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.

Topcoat over a vest and shirt
Instagram @ericrnycstyle

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.

Sweaters with Layers
Source: Reddit

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.

Layering Pieces for Men
Layering Pieces for Men

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.

TMM Button Up Shirt
A long sleeve button up shirt is the perfect foundation for layering up.

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.

GATs corduroys sweater 11
Wool sweaters – crew, v-neck or quarter zip – make a great second layer (over a button up shirt).

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.

Leather jackets for short men 1
A medium weight jacket, like a classic leather jacket, will get more wear than any other outerwear item in your closet.

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.

J. Crew Factory Walker Vest navy
A TMM favorite, the J.Crew Factory Walker Vest

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 charcoal quarter-zip layers well on top of the lighter denim button up shirt.

Wear this combo with jeans, chinos or even slacks, and you’re good to go.

Quarter zip with field jacket

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. Here the tucked look says “smart” while the sneakers say “casual”.

GATs corduroys sweater 11

Brown, navy and light blue look great together. You could smarten this look more by swapping the GATs for loafers.

Idea #4: A Henley Shirt with a Field Jacket

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

White sneakers jeans henley

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 leather jacket combination, as seen below, with jeans on bottom.

Flannel Shirt with a Leather Jacket
Flannel Shirt with a Leather Jacket

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.

Flannel shirt over henley

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.

Ash and Erie review 4

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.

Flannel with field jacket

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.

Casual Spring Layers

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

Idea #10: A Button-Down Shirt, A V-Neck Sweater and Quilted Jacket

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

Quilted jacket layers

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.

Cardigan with field jacket
Instagram @ericrnycstyle

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.

Quarter zip with field jacket

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.

Flannel and fleece with vest

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.

Denim shirt with leather jacket
Source: @thegentwithin

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.

Suitsupply 18

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

Idea #16: An Oxford Shirt, Quilted Vest and Overcoat

These last two ideas revolve around a classic wool topcoat (or overcoat).

Rajesh wearing blue shirt, navy jacket and gray pants

Choose a lightweight quilted vest as your middle layer if you’re looking for something more casual than a crew or quarter zip sweater.

Idea #17: Joggers, 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!

Topcoat with hoodie
Source: Pinterest

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 2-3 of them, then layer them from thinnest to heaviest and from lightest to darkest.

The result? Your “dressy” camel 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.

Thanh Pham casual layers
Instagram: @therealthanh

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.

Clothing and Style fall, layering, layers, winter

Related Posts

Outerwear for Short Men: The Ultimate Guide [2023]
Looking-at-watch ft
How to Wear a Flannel Suit (featuring Oliver Wicks)
Cold weather fabrics
The 14 Best Fabrics to Wear in Cold Weather
Lightweight vests
Lightweight Vests: My Favorite Middle Layering Piece

About Brock McGoff

The Modest Man founder, Brock is an aspiring minimalist who enjoys working out, spending time with his family, discovering new brands and creating great content.

Background: Brock McGoff has a bachelor's degree in psychology and a professional background in digital marketing. He believes that men's fashion is just one facet of self-improvement, and he started The Modest Man to help regular guys feel more confident by improving their appearance.

An east coast native, Brock currently lives in Arizona with his wife and daughter. When he's not working, he spends time with family, training BJJ, reading/listening to books and podcasts, and unsuccessfully trying to decide which movie to stream.

Expertise: Brock has built a men's lifestyle YouTube channel with over 400k subscribers. He's also worked as the creative marketing manager in a men's apparel startup. Brock has been quoted in, mentioned by or featured in publications like Esquire, Huff Post, Men's Health, WWD and Forbes.

More Articles by This Author

Facebook Twitter Instagram YouTube LinkedIn

Join the Club

Never miss a post, plus grab this free guide (instant download). No spam. Ever.

Subscribe Now

Reader Interactions

Comments

    Ask Me Anything Cancel reply

    Got questions? Want to share your opinion? Comment below!

  1. Philip says

    September 15, 2021 at 12:11 pm

    Too bad Peter Manning got rid of their solid color 1/4 zip sweaters.

    Reply
    • Brock says

      September 15, 2021 at 12:21 pm

      Yeah, I’d much prefer solid colors on that type of garment. Horizontal stripes aren’t the best choice for shorter guys, but I think if they were more subtle and closer together, they’d work a little better.

      Reply
  2. gegjr says

    January 17, 2020 at 1:04 pm

    Hi again,
    How about making your blog articles printable?

    Reply
  3. gegjr says

    January 17, 2020 at 12:57 pm

    Hi Brock, Good post. I often struggle with layers. Great tip that the lighter (color) goes under the darker. You mentioned 4 layers as being too much. I often wear a t-shirt under a shirt or a sweater (always in the winter but almost never in summer, I live in Indianapolis and we can have brutal winters) then top with a vest (Gilet or suit vest) then my outer jacket or coat. Sometimes the t-shirt shows under the shirt or sweater but I don’t count the t-shirt as one of the layers so is that ok?

    Reply
    • William Barton says

      January 17, 2020 at 1:58 pm

      Hey there! Glad you enjoyed the article! I think a good road could be picking up a v-neck shirt.

      T-shirts don’t add bulk, so really the 3-layer limit is a suggestion rather than a hard rule. If you’re cold, then for sure add more layers!

      But yeah, a simple v-neck would keep that extra warmth, but it wouldn’t pop through your other layers.

      Reply
      • George E Givens Jr says

        January 19, 2020 at 2:50 am

        That’s why you make the big bucks. 🙂

        Reply

Primary Sidebar

Join the Club

Never miss a post, plus grab this free guide (instant download).

No spam. Ever.

Subscribe Now

Top 5 Favorites for Fall & Winter 2022

  1. Thursday Boots Captain – still the best Goodyear-welted boot under $200 (full review here) 🥾
  2. Matte for Men SPF Lotion – because you should be using moisturizer with SPF
  3. Darn Tough Wool Socks – possibly the best boot socks you can buy 🧦
  4. Hamilton Khaki Mechanical – perfect everyday mechanical watch under $500 (Amazon/Jomashop)
  5. Flint & Tinder Waxed Jacket – great fit, perfect weight for fall 👍🏼

Trending Articles

Men over 40 style

How to Dress Well In Your 40s and 50s (and Beyond)

Fashion brands for short men

Where to Buy Clothes for Short Men (2022 Guide)

Seiko 5 SNK805

31 Great Watches For Small Wrists (Updated for 2023)

Best Business Casual Shoes for Men

Top 8 Best Business Casual Shoes for Men (2023 Guide)

Business casual outfits

The Complete Guide to Business Casual Style for Men

Topics

  • Clothing & Style
  • Outfit Ideas
  • Fitness
  • Product Reviews
  • Dating & Confidence
  • Grooming
  • Men of Modest Height
  • Income Reports

Footer

The Modest Man logo

  • Facebook
  • Instagram
  • Twitter
  • YouTube

Home • Blog • Resources • Contact • Advertise

 

Privacy Policy & Affiliate Disclosure • Terms & Conditions

 

As an Amazon Associate I earn from qualifying purchases.

 

Copyright © 2023 The Modest Man (Registered Trademark)