A Guy’s Guide to Fall Outfits: 3 Layering Tips From a Stylist

A Guy’s Guide to Fall Outfits: 3 Layering Tips From a Stylist

With 18 outfit ideas to wear right now
men's fall style tips

By Caroline Reilly | Last Updated: Oct 10 2023 | 10 min read

sponsored content created in partnership with Huckberry

Temperatures are dropping and if you’re anything like me—you’re rejoicing. Not only does it mean we all get to stop sweating through every piece of clothing we own, it also means fall outfit season is upon us.

Plaid shirts! Corduroy pants! Turtlenecks! Oh my!

Truly, the possibilities for staying cozy while looking cool in the fall (and winter!) are absolutely endless.

But just as dressing in the summer poses its own challengeslike facing the eternal question: How short is too short when it comes to shorts?!—I know that putting together stylish fall outfits for men can be tricky, too. 

Maybe you’re thinking: How do I stay warm without looking bulky? How can an outfit go from braving the elements outside to looking effortlessly sophisticated indoors?

The bottom line? You want to know how to look and feel your best in fall.

I’ve got one word for you: layering.

men's fall style tips

I know, that sounds simple. Suspiciously simple, even.

After all, everyone layers their clothes when the weather cools down.

Maybe you throw a sweatshirt over a t-shirt, so if you get too toasty you can take it off later. Or you add a quilted vest under your coat when raking the leaves.

But you’re here because you want to dress with more intentionality than just, “This plus this will keep me warm.”

You want your fall outfits to be both functional and stylish.

Which is great! Making an effort with your style without letting it take over your life is what I’m here to help with.

Today, that means showing you how to wear layers with style.

And we’re doing it all with some help from our friends at Huckberry!

Below, 3 tips for layering and 18 (!!) fall outfit ideas:

how to wear layers in the fall

1. The best colors for fall outfits come from fall foliage

One way to amp up any look is by adding more color to your outfit. But mixing and matching can feel overwhelmingmaybe less than mixing patterns (Does this paisley go with plaid??) but still.

You want to look cool, not like a Crayola box. I get it!

Thankfully, there’s an easy way to nail fall color combinations in your outfits. Just look to the trees.

men's fall outfit idea

henley | plaid shirt | pants | boots | hat | watch

Think about it. You’ve never seen a tree in September or October and thought to yourself, Yikes, that looks hideous!

From green to yellow to orange to red to brown, trees are a sight to behold when the leaves start turning colors in fall.

So, to achieve a look that’s both effortless and luxe, simply incorporate any and all fall tree leaf colors into your outfit!

how to wear layers in a fall men's outfit

jacket | sweater | pants | boots | beanie | socks

In general, warm colors like burgundy and burnt orange are great for fall.

What’s more, they pair super easily with neutrals like navy and tans, which makes them really easy to pair back to denim or chinos. They also layer great with tan sweaters or brown jackets. 

Olive green and red is another absolutely lush fall color combination.

Mix in soft neutrals like a camel-colored overcoat, and you’re good to go.

2. Work from thin to thick with your outfit layers

men's fall outfit idea with sweater and shacket

t-shirt | sweater | wool overshirt | pants | sneakers | sunglasses

This sounds pretty straightforward, right? Thinnest layers go closest to your body, then work outwards.

In this case, a t-shirt goes under a sweater, which goes under a wool shacket. Wearing your lightest layer closest to your body means that you don’t create unnecessary bulk as you build out an outfit.

This also means that the tried and true fall staple of many men’s youtha short sleeve shirt layered over a long-sleeve shirtno longer flies. Sorry not sorry!

men's fall outfits 2023

henley | blazer | jeans | boots | watch

For your thickest top layers, think: chunky fisherman knit sweaters, fuzzy tweeds, sturdy waxed barn jackets…

Really, anything Robert Redford would wear in a movie set in New England.

From there, just make sure each layer stands on its own in terms of thickness. If you’ve got a heavy fisherman’s sweater on, that should be your only layer of that weight and texture. So don’t layer, for instance, a half zip knit under a knit sweater. Or a wool chore coat under a wool peacoat. 

Instead, think: t-shirt then sweater. Or chambray shirt then cardigan. And on and on.

3. When in doubt, go for one hero textured piece.

Here at Style Girlfriend, we’re in the business of making getting dressed easier. One way that’s basically fool-proof? Build your outfit around one statement piece that makes you feel like a million bucks.

In the fall, maybe it’s a luxurious cashmere cardigan, or your favorite corduroy pants. Or a great pair of wear-everywhere boots.

monochrome men's fall outfit

sweater | short-sleeve shirt | jeans | sneakers | hat | sunglasses

In the outfit above, that cotton sweater is a total star! So why not build an outfit around it?

And if you’ve worked with me as a client, then you’ve heard me praise the wonders of monochromatic dressing.

Wearing different shades of one neutral color creates a look that is simple and refined.

It is one of my favorite and one of the most surefire ways to elevate an outfit.

In this case, the luxe, off-white sweater sets the tone for the whole outfit. You go from looking casual to looking tailored and slightly more formal without appearing like you’re trying too hard. 

This outfit formula is super simple because it allows you to build an outfit around pieces you already have.

men's fall outfit with trucker jacket

jacket | denim shirt | pants | boots | beanie

This jacket makes such a statement. It looks and feels super-sturdy, and you can surprisingly dress it down or up easily.

Depending on the temperature, you could layer it over a button-down shirt like in the outfit above, a sweater, or a flannel shirt. Even a t-shirt or henley.

On the bottom, this jacket goes with jeans, twill or corduroy pants, or chinos. Feel free to mix it up and not just wear this jacket one way!

More men’s fall outfit inspo
men's layered outfit for fall

Throw a wool shirt jacket over a deep red striped flannel shirt for an easy, stylish outfit.

how to wear layers men's outfit

Layer a denim shirt under an oatmeal-colored sweater. Finish the look with a “have it forever” jacket in leather or suede.

how to wear layers for fall

The ’90s are back, which means it’s time to pull that rollneck sweater you’ve had since Dawson’s Creek went off the air out of your closet.

men's layered outfit for fall and winter

More monochrome!

how to wear layers outfits for men

I never met a barn jacket I didn’t like. It’s the perfect top layer to any fall outfit.

men's layered fall outfit

There’s (almost) never a wrong time for plaid in the fall.

layered fall outfit

Pull out your dark denim to easily complement any fall outfit.

men's layer outfit with jacket

Fall style doesn’t have to be complicated.

monochromatic layered outfit for men

Stay in the blue and black family for a sophisticated, easy fall outfit.

mens layered outfit for fall and winter
how to wear layers outfit

Ready to warm things up, literally and figuratively? Add a puffer vest, which really only makes sense for a few weeks each year. This is that time!

how to wear layers men's fall outfit

If you looked up “how to wear layers” in the dictionary, there would be a picture of this outfit.


We’re teaming up with Huckberry this fall to help guys upgrade their cool weather wardrobe. Thanks for supporting the brands that make Style Girlfriend possible!