5 Stylish Sweaters So You Can Layer Up And Look Great In Chilly Weather

best men's sweaters Fall 2019 and Winter 2020

Millions of Americans are getting hit with a blast of polar air this week and that means it’s time to layer up. Elsewhere, you can still get away with just wearing a sweater and you don’t need to toss in a jacket just yet.

I wanted to put some of the best Fall 2019 and Winter 2020 sweaters on your radar so you bros can upgrade your sweater game as we wade knee-deep into Layering SZN. Some of these are pretty straight forward styles made with premium materials and others are a little funky (in a good way). You can purchase all of them or pick and choose your favorites by following any of the links below.

First up, we see the Schott Button Henley Sweater. This is your classic, no-nonsense sweater made from a nylon and wool blend that fit’s great and won’t ever clash with your winter outfits because it fits with everything. The thermal waffle weave is designed to keep you warm and the classic henley silhouette will frame your body well.

best men's sweaters Fall 2019 and Winter 2020

The second sweater comes from the same brand (Schott) that’s infamous as the creator of the modern American leather jacket. The Schott Men’s Pullover Sweater has a smooth and comfortable pullover silhouette with a cozy shawl collar. This is my preferred collar style through most of Winter because it tends to frame your face and shirt collar really well. You can pull it off with a t-shirt underneath or an oxford shirt. This sweater has a wooden hook-and-loop style closure on the neckline, ribbed cuffs + waistline, thick cable knitting, and it’s made from a very comfortable blend of wool and nylon.

I’ll be honest, my favorite sweater in this roundup is the Peregrine Funky Jumper. The contrasting Navy + Olive sleeves work so well together. You can pop your collar underneath this sweater (or not) and it will look great. The Funky Jumper is made from 100% British wool sheared from Yorkshire-raised sheep in the UK. I’m a big fan of the vertical rib-knit construction for clean lines that fall in line and frame your body well while always retaining its shape.

best men's sweaters Fall 2019 and Winter 2020

The Flint and Tinder Shaggy Scottish Sweater is another interesting look with a Navy body and Forest sleeves + shoulders. This remarkably comfortable sweater is made from 100% brushed wool that comes together in a classic Fisherman’s crewneck design that never goes out of style. The cuffs, hem, and neckline are all rib-knit and this sweater is made in Scotland by folks who know a thing or two about needing to stay warm year-round.

The last sweater in this roundup is the brainchild of two heavyweights in the cold weather apparel game. The Smartwool x CHUP Hansker Half Zip Sweater is made from a super soft Merino wool blend. If you’re not familiar with Merino wool, it’s probably one of the best fabrics on the planet. It’s antimicrobial, temperature regulating, sustainably-sourced, and odor-reducing. You can wear this sweater A LOT longer than your others before cleaning. The stylish half-zip design should be a staple of every man’scold weather wardrobe so definitely consider this as an excellent option.

Let’s check out all of those sweaters one more time. You can purchase any of the sweaters by following the product links underneath the image below.

best men's sweaters Fall 2019 and Winter 2020

[1] Schott Button Henley Sweater [$80]

[2] Schott Men’s Pullover Sweater [$105]

[3] Peregrine Funky Jumper (Navy/Olive) [$145]

[4] Flint and Tinder Shaggy Scottish Sweater [$168]

[5] Smartwool CHUP Hansker Half Zip Sweater [$180]

best men's sweaters Fall 2019 and Winter 2020

Looking for more Fall Fashion options? Check out this roundup of the best ‘Functional Pants for Fall‘. Here are 5 stylish shoes perfect for Fall. Are you looking for other styles of boots? Peruse this selection of the Best Chukka Boots For Men. You can check out this collection of the 14 Best Hiking Boots For Men. You can also check out this list of 5 gifts under $50 if hou’re looking for something random.

By the way, if you know of a product that should be featured here you can hit me up on email at cass@brobible.com, or find me on Twitter at @casspa. Or if you’ve got an idea for a daily theme I should touch on then hit me up!


The BroBible team writes about gear that we think you want. Occasionally, we write about items that are a part of one of our affiliate partnerships and we will get a percentage of the revenue from sales.