How to Layer Men's Clothing

When cold weather arrives, it’s never difficult to distinguish the well-dressed men from the—well, shall we say—not so gifted in the closet department? That’s because the most stylish men among us know how to layer for fall and winter without looking like a linebacker.

Luckily for everyone, layering really isn’t that difficult. All you need to do is get the basics down, equip your wardrobe with a few hardworking pieces, learn a few tricks and boom–you’re officially a master of cold-weather layering.

Sounds simple enough, right? So, grab your hot cocoa, settle down by the fire and put on your manliest-looking snuggie (there’s no shame in the snuggie game). We’re going to teach you how to layer like a pro.

Stock Up on Fall & Winter Essentials

First things first: You should start building your wardrobe with functional and stylish pieces. The right style staples can instantly elevate your business casual attire and make figuring out how to layer clothes a total snap in the morning. 

Needless to say, you want to choose your key players wisely. So, which pieces should you be adding to your all-star lineup? 

Regardless of what Mother Nature has up her sleeve, these are the menswear items you should consider keeping in your heavy rotation:

Inner Layers

Casual Button-Down Shirt: The casual button-down shirt is every man’s secret weapon to looking and feeling good in cold weather. Pair it with your fleece vest for a match made in heaven.

Dress Shirt: Need to impress the C-suite or close a deal? Replace your casual button-down shirt with a crisp button-up dress shirt, its more sophisticated sibling. Add a tie and layer it with a gray crew neck sweater to channel your own boss vibes.

Performance Polo Shirt: Toeing the line between casual and business casual, the performance polo shirt is one of your most versatile players. Pair it with your bomber jacket for a street smart look or wear it with a sport coat for happy hour and beyond.

Sport Shirt: When you want to look good without sacrificing comfort or style, the sport shirt is your go-to piece. True to its name, the sport shirt is always ready for action—despite looking right at home in an office setting.

Mid Layers

Crew Neck Sweater: The classic crew neck sweater is the foundational sweater every man needs in his closet. Stock your wardrobe with a few neutral crew necks (gray, navy, etc.) and one or two bold hues as well.

Quarter-Zip Pullover: Ditch your Mark Zuckerberg-esque hoodie and say hello to the men’s quarter-zip pullover, a comfy mid-layer that looks as good as it feels.

Midweight Vest: Cozy and practical, the midweight vest is a must-have fall and winter essential. Partner it with your favorite plaid flannel shirt and don the look for all your outdoor escapades.

Denim Jacket: The classic denim jacket is a must-have layering piece that’s worth its weight in menswear gold. This versatile jacket can be paired with virtually everything–from cardigans to t-shirts and even a sleek, leather jacket. 

Outer Layers

Sport Coat: Granted, a sport coat isn’t going to stand up that much to Old Man Winter. However, it makes up for this small shortcoming by being an excellent transitional piece in the fall and early spring.

Camel Trench Coat: Sophisticated and refined, the trench coat is one of the few outerwear staples that works flawlessly with a suit. The only downside is that it can give off detective vibes if you’re not careful. Just remember to keep your magnifying glass and deerstalker hat at home and you should be fine. 

Shearling Jacket: When you live in a place where the cold air actually hurts your skin, you need a shearling jacket. Ridiculously warm and boasting timeless style, this wool-lined jacket oozes manliness and rugged style.  

This list focuses on top pieces because, obviously, there isn’t any layering going on with your bottom half other than your pants and boxer shorts. That being said, you should invest in at least a few classic blue jeans (opt for dark wash to keep it business casual) and some khaki pants to complete your cold-weather look.

 Learn the Style “Rules” of Layering Clothes 

To master the game of layering clothes, you first need to learn the rules. We can already feel your inner teenager rebelling against the thought of following arbitrary fashion rules. 

Before you go full fashion anarchy on us, just pretend the following “rules” are just simple guidelines (that you really, really ought to follow):

Go from thin to thick. This rule dictates that you should always wear your thinnest garments closest to your body and layer on top with thicker pieces. Ignore it and you’ll be sweating so much in your business casual attire that your boss might just decide to buy flood insurance on the spot.

Mix up your proportions. Ideally, all your pieces should be different sizes, with the first layer being the shortest. So, say that you have a button-down shirt as your base layer and you’re layering with a sweater. The hemline of your sweater should extend past the hemline of your button-down.

Every piece should have a function. Speaking of shirts that peek out, any visible layer in your attire should be something you can wear on its own. Don’t wear a button-down shirt with a tomato stain on the front just because your sweater will cover it. If you find yourself sweating at the office, you don’t want to be trapped in a layer that can’t be removed thanks to last week’s Lasagna Mishap of 2019.

Keep patterns and lighter colors closer to your body. While you can definitely bend this rule, it’s worth following for a failsafe layered look. To give you an example, you might wear a light blue gingham shirt and a dark blue crew neck—as opposed to a dark blue button-down and a striped crew neck. Likewise, a striped polo shirt would pair well with a dark sport coat.

Add Interest with Color, Pattern, and Texture 

Cold weather essentials? Check. Knowledge of layering principles? Check. Now, it’s time to take layering for men to a new level by incorporating various colors, patterns, and textures into your outfit—because you’re not a boring guy, right? We didn’t think so.

If you’re ready to venture out of your style comfort zone, here are the color, pattern and texture tips you need to ace your cold-weather layering:

Learn the art of color mixing. Not to freak you out, but color mixing might be one of the trickiest things to learn. Don’t let that stop you from learning a thing or two about color theory, which is basically a cheat sheet for knowing which colors look good together. Once you learn the basic principles of color theory, you can begin to understand how Ryan Gosling can step out in a navy suit and a yellow vest (a sweater vest, no less) without looking like he got dressed in the dark.

Incorporate contrasting layers. Once you know which colors pair well together, you can start playing with contrasting colors. These are colors that are opposite each other on the color wheel. Contrasting colors look best when you alternate them in your layering. So, let’s say you start with a light blue dress shirt with a striped yellow and navy tie. You might add a solid yellow cardigan and complete the look with a dark navy overcoat.

Mix up solids and patterns. Similar to how you would alternate contrasting colors, mixing up your patterns and solid colors is important to layering with finesse. So, if you’re going to rock a plaid suit (a bold move, but we’re into it), start with a solid colored dress shirt and a textured tie to avoid too much distraction in your outfit.

Don’t be afraid to go tonal. Enough about contrasting colors—why not try tonal layering instead? Although part of you might be shying away from wearing an all-gray outfit for fear of being too boring, it’s a style move that will earn you some admiring looks. The secret to pulling off the look is to switch up your fabric textures and patterns. For instance, you could pair a gray wool cardigan with a sleek gray dress shirt and a patterned gray tie.  

How to Layer Shirts, Jackets, Sweaters and More

Are you still with us, guys? Then, congratulations! You’ve learned the basics of layering clothes and get an A+ for making it this far. 

Unfortunately, we don’t have anything you can stick on your fridge to show off your newfound style knowledge. We know, we know: How else is your girlfriend going to know that she’s in the presence of a true layering genius?

You can always impress everyone with your layering skills by putting what you’ve learned into practice. Before we send you off into the wild, here are a few of our favorite ways to layer all of your essential cold-weather pieces:

Layering Shirts

• Polo Shirt with a V-Neck Sweater: Remember your style lesson about adding color to your layers? Good, because this polo shirt and V-neck sweater combo will put your skills to the test. Start with a polo shirt in a bold hue (think salmon or deep purple) and layer with a V-neck sweater in another vibrant—yet complementary—shade. The interesting color combo will help kick those winter blues away and energize your entire workweek.

• Long Sleeve T-Shirt and a Vest: For the guy who orders his coffee straight black, the long sleeve t-shirt and vest combo is the simple, no-fuss look that gets the job done. Though it’s not necessarily appropriate for your 9-5 grind, this hassle-free combo is more than ready to take on weekend errands and family outings with confidence.  

• T-Shirt, Sweater and a Jacket: When temperatures haven’t yet dropped to omg-I-can’t-feel-my-face levels of cold, skip your outer layer and just wear a shacket (t-shirt + jacket) over a t-shirt and a crew neck sweater.

Layering Casual Button Down Shirts 

• Button Down Shirt, Quarter Zip Pullover and a Sport Coat: Nothing screams business casual more than this style trifecta. To nail this look, start with an Oxford sport shirt in a checkered pattern and follow its color scheme with the rest of your layers. For example, if your sport shirt is brown and blue, choose a blue pullover and top off the look with a brown sport coat. Boom—cold-weather style at its best, gentlemen.

• Plaid Button-Down Shirt with a Casual Vest: Is there a more authentically outdoorsy pairing than the plaid button-down shirt and casual vest? This look is a slight step up from the long sleeve t-shirt and vest combo while still being super casual. Word to the style-wise: If you want to rock a puffy vest with your button-down shirt, let them be your only two layers. Otherwise, you’ll look like you went way too hard with the eggnog and pumpkin pie this holiday season.

• Shacket with a Denim Button-Down Shirt: For a little button-down shirt inception, try wearing a shacket on top of a denim button-down shirt. The denim layer adds interest to your look and pairs perfectly with a navy shacket. Just make sure that your shacket is made of a heavier fabric than your denim button-down shirt; otherwise, it will throw the entire look off. 

Sweater Layering 

• Dress Shirt, Cardigan, and an Overcoat: When cold weather threatens your polished and professional style, bring out these three heavy hitters for a refined, work-ready look. Start by choosing a polka-dot tie that will peek out from your dress shirt and cardigan. If you want to mix patterns, layer with a striped dress shirt and choose a solid-color cardigan. Finally, top off your ensemble with a camel overcoat. If there’s a chest pocket, opt for a pocket square to add a bit of flair to your cold-weather attire.  

• Crew Neck Sweater and a Suit: Sure, the cardigan sweater may be the suit’s true partner-in-crime. But a casual crew neck sans tie and dress shirt will give your suit a sportier, more relaxed vibe. Finish the look with a clean pair of kicks for a bold fashion move that only the most stylish of men can pull off with swagger. 

• Chunky Knit Sweater with Flannel Button-Down: Pair your hardest-working flannel with a chunky knit sweater for a cozy-casual look. Whether you’re chopping wood, relaxing by the fire or hailing down a taxi in the slush, this winning combination has you covered on all (cold) fronts.
  
  

How to Layer Jackets 

• Jean Jacket and a Shearling Jacket: All we’re saying is that if Bruce Springsteen can layer a jacket on a jacket, then why can’t you? Take a tip from the music legend’s style playbook by rocking not one, but TWO classics: a denim jacket and a shearling jacket. Both jackets promise to keep you warm yet wicked cool all winter long.

• A Maritime Jacket, Pullover and Casual Button-Down Shirt: From seaside adventurer to weekend warrior, wearing a maritime jacket will give you a laid-back look that speaks to your effortless sense of style. Pair it with a pullover and add a bit of pattern with a checkered button-down shirt for a practical outfit that is sure to keep you warm and dry. 

• A Topcoat and a Vest: For a tonal look, combine a tan topcoat (which is essentially a lightweight overcoat, in case you’re wondering) with a tan vest. Create contrast underneath with a solid color, light blue shirt, and a dark navy tie. Finally, round off your look with navy colored pants and a classic pair of brown Oxfords. Honestly, if this outfit doesn’t land you business deals or a hot date, then we’re not sure what will.
  
  

From Style Zero to Cold Weather Hero

When the weather turns ugly, you don’t need to follow suit with a boring, shapeless outfit. With the right layering techniques, you can winterize your wardrobe the right way and take your layering to next-level greatness. At the very least, you can finally stop sweating in your cubicle every time that one coworker jacks up the thermostat in your office building. And for that, you’re welcome.