Skip to main content
  1. Home
  2. Fashion & Style
  3. Evergreens

Layering clothes: Men’s fashion essentials to transition to cool-weather style

How to layer clothes with essentials every man should have

Man in henley and cardigan
Sherman Yang / Unsplash

Fall weather can change by the hour. You can head out for a morning jog bundled up. Then, you head to work in a sweater and slacks, only to wind up wishing you wore something lighter by the time lunch hour rolls around. At that point, it’s so warm you can eat outside. Head home from work as the sun sets (beautiful but depressing), and suddenly, you’re freezing.

Figuring out what to wear can be more complicated than your workday. Layering clothes can have you ready for everything Mother Nature throws your way. Certain pieces give you the freedom to wear them when needed and shed them when not. It can seem challenging — another item to match your outfit. However, five classic pieces make layering outfits a cinch. Here’s how to layer clothes for cold weather.

Recommended Videos

Laying clothes: The essential pieces you need

Pullover crewneck sweater

a man in a crewneck sweater speaking with a woman in a blazer
Image used with permission by copyright holder

Crewneck sweaters never seem to go out of style, making them a staple worth stocking up on for cooler months. Not only are they classic, but they also layer well over T-shirts, polos, and button-downs. You can also throw blazers or leather jackets over them, depending on what the occasion and weather call for.

Play with different styles and textures. Rib-knit cuffs allow you to roll up your sleeves and allow other layers, such as button-downs, to shine through, too. Or, opt for three-quarter sleeves for an even more layered effect. Cable knit crew necks ooze cozy vibes. It’s worth opting for one in several colors, so you can mix and match as you become a pro in how to layer clothes for cold weather.

Light, waterproof jacket

April has a reputation for being the rainy month, thanks to the old line, “April showers bring May flowers.” Fall isn’t immune to rain, though. It’s hurricane season, and even areas not typically in the eye of storms can catch remnants of them. A light, waterproof jacket is easy to layer during chilly mornings or evenings, rain or shine, and pairs perfectly with boots.

Opt for a classic yellow slicker to stand out. Tan,  black, or gray ones offer a more muted look. A longer trench coat looks more formal and will keep legs dry, while a shorter raincoat gives off more casual vibes and may make going from workout to work a breeze.

Cardigan blazer

You likely have plenty of blazers and cardigans. However, a hybrid of the two is worth trying on for size (and style). It’s what it sounds like — a sweater with lapels, a la a blazer. The piece adds a unique layer of style and presents a happy medium between the formality of a blazer and the cozy, casual feel of a cardigan. The cardigan blazer works with any under-layer, from a crisp button-down shirt to a light V-neck.

Vest

Man looking in the mirror with a vest and tie
Pexels

Vests add a little extra warmth but won’t leave you sweating on a breezy 60-degree day. There are plenty of styles to choose from. Solid wool, cable knit, and argyle are work-wear classics. Pull them over collared button-downs and even ties for a timeless look.

Puffer vests are versatile outerwear pieces that can be used to layer clothes while commuting, running errands, and skiing. A red vest will make you stand out in the store or on the slopes. However, more subtle colors, like forest green, black, and navy, are available at major retailers, from Macy’s to Amazon.

Long-sleeved T-shirt

Like the crewneck sweater, a long-sleeved T-shirt is an essential piece for layering clothes, and you’ll want several for your rotation. They make for comfortable undershirts and can prevent a cable knit sweater from feeling itchy. However, you can also showcase them while looking effortlessly stylish when paired with a vest or underneath a cardigan blazer. Opt to have a variety of colors in your wardrobe, from bright greens and blues that pop to basics like white, black, and navy.

Knowing how to layer clothes for cold weather is a clutch skill during the fall months when Mother Nature’s plans are anyone’s guess (including your local meteorologist’s). Rain, sun, clouds, heat, cold, and even snow are all potential forecasts in certain parts of the country. Layering clothes doesn’t have to be complicated, though. Investing in key pieces like vests, long-sleeved T-shirts, and crewneck sweaters will give you the necessary building blocks.

When layering clothes, playing with texture can add an element of style. A crisp button-down shirt with a cable knit sweater or sweater vest will have you looking timeless without boring. You can also freshen up looks by rolling the sleeves of your top layers at the cuff, which shows off the bottom one, too. Have fun with it, and opt for pieces and colors that suit you.

Some basic tips for layering clothes for fall

Trendy handsome man posing in autumn park alone
Shutterstock

Now that you have the essentials for layering your fall outfits, let’s give you some simple tips for layering that will help you put together the best outfit for fall.

Match your colors

When layering your outfit, you want to make sure the colors of all the pieces work well together. You don’t have to be monochromatic (unless you want to be); just make sure the colors look good together. The best advice for fall outfit colors is to choose warm colors. Think of the colors of fall leaves like green, red, yellow, orange, and brown, and you’ll look great.

Start thin and move to thick

When it comes to layering, you want to have the thinnest layer closest to your body and then add the thicker layers on top. Start with a T-shirt and work your way outward with a sweater, vest, etc.

Hockerty wants color to stand out this summer with new Color Edit
Stand out with new summer colors from Hockerty
Blazer, Clothing, Coat

The summer is in full swing. That means you are likely dealing with the rising temperatures to the point that you are sitting back and missing the blizzards of January. I remember standing on the corner of a street in New York and watching the snowflakes fall, thinking, "I can't wait for summer and baseball." Now, I am looking back and thinking about those temperatures, and I am wishing I had enjoyed them more. As I bake like a chicken on the streets of New York, I think about how to dress for the office while dying of heat stroke. The answer? Hockerty's new Summer Edit brings light and breathable fabrics while also adding in the kinds of colors that will take your wardrobe from stylish to functional without leaving the style behind.

More than suits

Read more
Luminox’s new Adventure Watch trades tactical black for a weathered, vintage look
The Swiss brand's latest field watch wears a pre-aged "IP Antique" finish and leather straps, priced at $795.
Wristwatch, Arm, Body Part

Luminox usually builds watches that look ready for a covert night operation — but its newest one looks ready for a 1950s expedition instead.

The Pfäffikon, Switzerland–based brand just dropped the Adventure Watch, a field watch styled after the timepieces of the early exploration days but built to Luminox's modern military-grade standards.

Read more
What sailors in the Race to Mackinac, America’s oldest freshwater race, wear on their wrists
The race from Chicago to Mackinac Island is a days-long battle against the Great Lakes. In that kind of contest, you need a watch as tough as the job.
Boat, Sailboat, Transportation

The Race to Mackinac has been run since 1898, when five boats set out from Chicago. Today it covers 333 statute miles up Lake Michigan, crosses into Lake Huron at the Straits of Mackinac, and finishes off Mackinac Island — and it is not an easy voyage. It is also not a gentle one. Sustained gales flattened big chunks of the fleet in 1911, 1937, and 1970, and after a deadly storm in 2011, the Mac's reputation for danger stopped being theoretical. The fastest boats finish absurdly quickly now, with an all-time record of 18 hours and 50 minutes set back in 1998, but most crews are out there for two or three nights. The sailors alternate, sleeping in shifts of four hours each, until they (hopefully) make land.

It might seem tough to imagine doing that once — now, try doing it two dozen more. For those who make the journey at least 25 times, the prize is entry into the Island Goats Sailing Society, founded in 1959 and now several hundred strong. Rack up 25 Chicago Macs and 25 from Port Huron, and you become a Double Goat. The nickname, as the story goes, comes from the aroma a crew carries after days at sea with no shower. All things considered, this is a tough, electric, occasionally dangerous race. The Chicago Yacht Club hosts the race annually in mid-July, and that's exactly where I went to look at watches.

Read more