A Guide to Layering 10 Types of Outerwear

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It's best if you keep it simple with your waxed-cotton jacket. If you own something from Barbour, you just need to throw on an oxford shirt and a merino wool sweater and be about your business. You'll be warm, dry, and possess a look that won't get you any crap from your stylish friends. Waxed-cotton jackets and sweaters are playing it safe, but it's better to not be soaked than to take a futuristic style risk that doesn't pan out.

It's too cold most days this time of year to wear a denim jacket with just a T-shirt, but you should view this piece of outerwear as something to be thrown in the mix with other pieces of outerwear. Sure, you can layer underneath and dress like a rancher, but you can also use the denim jacket as a heavier version of a denim shirt. You can also wear your denim jacket with a blazer or any other buttoned-jacket that's made from cotton or wool. The denim jacket is as versatile as Sriracha, and, like the sauce, should be applied generously to your daily goods.

A bomber jacket can come in a variety of fabrics and constructions, but they're ideal for someone who doesn't want to deal with a jacket that's too heavy or complicated. We've seen people get as extreme as wearing a double-breasted jacket underneath a bomber, but the jacket's cropped design will allow you to get next level with your layering possibilities. This is the perfect time to throw on a super-long T-shirt underneath and pile cozy layers on top.

You shouldn't think of a trench coat as just a boring piece to put over a blazer. While that's the standard way of doing it, you can also rock unexpected pieces underneath. Kaney's long tee with a zip-up hoodie under a full trench makes for a surprisingly dope look. This is opposed to what most dudes/flashers rock under their trenches, which is hardly ever surprising, and never ever dope.

Don't assume that a blazer has to be worn with a shirt and tie. Don't get us wrong, you can roll with that look, but for the sake of keeping toasty, you'll want to layer up. Try a quilted vest underneath your blazer to kick around in on the weekends. Or grab a light, technical jacket and wear it over your blazer. A denim jacket is also fair game and will be best if it's washed or actually vintage. If you really want to blow minds, unzip a bomber jacket and wear it under your blazer. This advanced move works best with unstructured blazers made of tweeds or other less formal materials.

Every guy should own a solid parka jacket. If not for the jacket's stylish benefits, then cop for its functionality and performance in the elements. Parkas are normally roomy jackets, which means you can layer a bunch underneath them, but they're usually warm enough that they don't need too much work. Essentially, whatever you want to wear that day—sweatshirt, baseball jersey, longsleeve T-shirt, button-up shirt, whatever—will all fit under your parka and you'll still be warm. 

Common logic would dictate that a windbreaker should be left back in the spring, but they're a perfect top layer for wearing heavy knits in the fall. What they lack in warmth, they make up for in being steezy and—like their name suggests—blocking the wind. Chunky sweaters will make you feel warm and toasty and can be worn deep into fall just a windbreaker over them. You can even place a fleece jacket underneath a windbreaker and have enough room to breathe. Plus, when windbreakers are zipped up, they do a decent job of retaining your body heat.

Leather and biker jackets are surprisingly breatheable in warmer months but will always find their true home in the fall. There's the temptation to wear a leather jacket undone with a graphic or plain white T-shirt underneath, but wearing them with a crewneck sweatshirt and an oxford shrit is just as classic. You'll have on three different fabrics that all stand out in their own way and work together to produce enough heat to make it through the end of the year.

Fleece jackets are one of the most comfortable and versatile pieces of outerwear out there. You can easily wear a fleece jacket with a longsleeve or button-up shirt underneath, but they can also be used as a layering base. If you're the outdoors type, the go-to look is with a down vest over top, but a fleece jacket can also be placed underneath a lightweight parka or shell for when it gets colder to give you the right amount of warmth.

The best thing about vests is they can be worn almost year round, and can be integrated into outfits depending on how much or how little warmth you need. It's easy just to throw on a vest over a button-up shirt and call it a day, but you can also get advanced with this sleeveless garment.

Depending on what the vest is made of, it can be layered under virtually any other piece of outerwear. Vests made of denim, fleece, or are quilted can be easily worn with almost every type of outerwear, and you'll be set for whatever the thermometers read. But if you want to keep it simple and rock a vest and a hoodie, go for it.