The Only Men’s Fall Fashion Guide You’ll Need in 2021 to up Your Style

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by  William Barton | Last Updated: 

You’re excited to wear more than just a t-shirt and shorts, but it’s still too warm to throw that overcoat on. So what do you do in the transition period from hot to cold?

Fall is widely touted as the top season for fashionable guys, and when you’re done reading this guide, you’ll know exactly how to boost your style game in autumn.

Whew, I was starting to think summer would never end. 

I live in North Carolina, and it doesn’t really get cool here until November, but the dead heat of summer has passed and I’m busting out the best pieces in my wardrobe for fall. 

If you’re looking to pick up a few staples as the leaves change this year, you’re in the right place. 

I’m going to cover what types of clothes to wear for fall, the colors you should be choosing, and sporting a few outfits to bring some inspiration.

Best Colors to Wear for Fall

Men are generally quite comfortable with fall colors—they’re usually muted and deep. 

But don’t take that as an excuse to wear a black t-shirt and jeans every day. There’s so many other color options in fall, so it’d be a shame to miss out. 

linen chore coat fall colors

If spring is all about bright, punchy colors, fall is just the opposite. Bust out your burgundy sweaters, indigo jeans, grey chinos, and mustard chore coats.

I tend to wear cool colors on bottom (blue jeans are a go-to) and warmer colors on top. If it’s a bit chilly outside, you can wear a warm color over a neutral, like a mustard shirt over a charcoal tee.

denim jacket fall colors

White should stay in spring and summer, and the same goes for bright, saturated colors. 

Consider the image above: yes, I’m wearing yellow, but it’s far from what you’d expect to see on a sunflower petal. 

The key is to combine that pop of color with subdued and deep neutrals. 

denim chore jacket with red fall colors

If you’re not a big fan of color, you can also stay completely in the neutral family, though I recommend picking up one neutral that’s on the warmer end of the spectrum, like a khaki or brown. 

Pair that with as much light grey and charcoal as you want—though I’d stay away from a pure black if your only color is brown. 

linen shirt fall colors

It’s also just as important to consider the texture of your clothing as it is the color. 

For instance, fall is an excellent time to bust out a quilted jacket, suede shoes, waffle-knit henleys, and wool trousers if you have them. 

As you layer your textures, you’ll get a more refined and classy fall look. 

quilted jacket fall colors

Don’t be afraid of color in fall, and don’t fall into the trap of going neutral—there’s plenty of time for that in winter. 

When in doubt, look at the color of the trees around you—they’ll supply you with more than enough color inspiration. All those oranges, reds, and yellows are perfect for picking out the best fall colors. 

Choosing the Right Fall Jackets and Sweaters

There are two phases in fall—or at least that’s true where I live. There’s the warmer end of fall as you transition away from summer, and then there’s the colder end where you wonder if you should swap out the heavy shirt for a jacket. 

This is where having a set of versatile staples is important. 

One of my favorite pieces for when the evenings start to cool off is the Banana Republic Indigo Linen Chore Coat.

Banana Republic 6

It still has remnants of summer (due to the texture of the linen), and it’s indigo coloring is deep and rich, so it’s a perfect transition piece. 

I like layering a lighter shirt underneath the chore coat—especially something with some added texture like the Banana Republic Linen Henley Tee.

Because they’re both linen, the textures naturally match, and the breathability makes this combo a great option for guys who run a bit hot and want something that’s cooler in the day but still offers a break from the briskness of sundown.

Nisolo model wearing javier chelsea boot

As the season progresses, I like adding denim on top with something like the Everlane Denim Chore Coat

Chore coats offer an excellent middle ground for fall as they’re not too heavy, but can easily keep a chill off. 

model wearing grey chinos and black ace marks troy chelsea boots with green shirt

Of course, even heavyweight shirts aren’t going to cut it as you get to the tail end of November, and that’s when it’s time to consider throwing on something like a bomber jacket or a thick hoodie. 

model wearing Grant Stone Brass boot

When it comes to jackets, I usually prefer something with some texture, like a quilted bomber. The added intrigue helps these lighter jackets stand on their own as the center of an outfit. 

As winter sets in, a bomber works well as a layering piece, too. Not all climates require that many layers, so you might be able to get away with just a bomber throughout all winter (I can do that in North Carolina, but New Yorkers won’t feel the same). 

model wearing knit cardigan and dark blue jeans

Fall is also a fantastic opportunity to bust out your sweaters. A lot of guys like the standard crew neck sweater look, and those can be a great chance to add color. I don’t really like the way those look and I usually steer toward something a bit more chunky like a shawl-neck. 

If you want something versatile you can take with you into winter, try a shetland sweater. They’re excellent transition pieces into the cooler part of the year. 

4 Best Shirts to Wear in Fall

I doubt I’m the only one who gets sick of wearing t-shirts by the end of summer. 

I’m usually dying to wear something a little more interesting, and the cooler weather of fall is always welcome.

Linen

Banana Republic model wearing linen chore coat and traveller chino 1

Linen is known as a summer fabric, but for many people, warm weather persists well into October. 

That’s why I like to keep some linen transition pieces. Throughout much of the U.S south and west, temperatures can hover around 70F (20C) degrees throughout the day, but drop to 50F (10C) in the evening.

If you’re out on the town walking around all day, but plan on hitting a patio bar in the evening, that can lead to either sweating like crazy all day or getting the shivers at night. 

Banana Republic outfit on model 1

But with a linen overshirt like the Banana Republic Indigo Linen Chore Coat, I’m able to stay cool throughout the warmer part of the day and the long sleeves keep the chill away in the evening. 

Flannel

model wearing blanket shirt from outerknown with leather bag

Flannel is a fall classic that looks fantastic both layered and by itself. 

I’ve seen a lot of guys go crazy and stock up on a dozen flannels to the point that it’s all they wear through fall and winter. 

Yes, I love a good flannel, but don’t go overboard. Having a few flannels—maybe one with a unique plaid pattern like the Outerknown Blanket Shirt shown above, and another solid color like the Tom Beckbe Flannel shown below. 

Tom Beckbe 13

Don’t skimp when you’re picking up a flannel. The quality of the fabric makes a huge difference in the finished product. Subtle details like how the collar falls and how the placket holds up can either make you look put together or look more like a slob.

Oxford Cloth Button Down

Frank and Oak oxford shirt tucked into Rhone chinos

Oxford Cloth Button Downs, otherwise known as OCBDs, are a wardrobe staple year-round, but you can really get a ton of mileage out of them in the more temperate seasons. 

They’re not the same as dress shirts—they’re more casual than that. Many guys wear these to the office, which is fine if you have a business casual dress code, but the OCBD doesn’t count as a formal piece. 

In fall, stick with the color palette outlined above for your OCBDs. Stay away from white. If you’re afraid of color, try wearing a colored t-shirt underneath a neutral, unbuttoned OCBD. That’ll still give your outfit a pop of interesting fall color, but you won’t be “all in” on the colored t-shirt. 

Henley

Banana Republic linen cotton chore coat

I love henley’s year round—they’re the t-shirt’s unpredictable little brother. Try sporting a long sleeve henley if the weather permits a single layer. I find long sleeve tees to be boring, but you add three buttons and a placket, and suddenly you have a sharp looking outfit. 

The true benefit of henleys, in my opinion, is in layering them underneath a heavy work shirt or jacket. 

Kodiak Boots rover 2 winter chelsea boot with Vibram arctic grip sole

There’s something undeniably cool about leaving the top few buttons of a henley undone, peaking out at the top of your work shirt. The style gives off Anthony Bourdain vibes like, I can’t be bothered to check the mirror because I already know I look awesome. 

Sneakers vs Boots in Fall

Thursday Boots Logger on model near river

You were wearing sneakers all summer long (when you weren’t wearing flip flops at the beach). It can be tempting to keep the streak alive and continue slipping on your most comfortable sneakers through fall, too.

But you’re missing out on one of the finer aspects of fall fashion: boots. 

Each guy has his own perspective on boots: some want a huge beefy work boot, others like a slimmed down and classy Chelsea boot. Still others prefer the middle ground with a service boot. 

You can’t really go wrong, except if you decide to wear sneakers throughout fall. 

moc toe Grant Stone Brass boot black

That’s not to say there isn’t a place for sneakers. I’ll still bust out a darker pair of sneakers like my black KOIO Capri’s from time to time, but more often than not, you’ll find me wearing a pair of Thursday Captains.

How to Layer for Fall Weather

model checking pockets of suede leather jacket

There are a few key rules to consider when layering. These also apply to your winter outfits, so take these to heart.

  1. Wear lighter colors closer to your body.
  2. Wear thinner fabrics closer to your body.
  3. Don’t mix hot weather and cold weather fabrics (i.e. don’t wear a linen t-shirt with a heavy flannel on top).
  4. Wear patterns closer to your body and solid colors further out (i.e. a checkered shirt with a solid color quilted vest on top).

Those may seem intuitive to you, but if not, take another look through the photos in this article. You’ll notice those rules in place in just about every image (except for a few where I’m wearing a black t-shirt underneath lighter color heavy shirts. But I’m still abiding by rules 2,3, and 4).

My wife really likes it when I wear brighter colors like yellow and orange, but they’re definitely not my go-to. Layering is the perfect way to tone down a shirt you’d normally skip. 

Changing Leaves

All the principles you learned here can be applied to winter and spring, so you’re good for at least another six months. 

Just swap out for new colors and different fabric weights. 

Summer is its own beast. But you’ll find that many of the items you pick up for your fall wardrobe will blend seamlessly into other seasons, too.

When in doubt, find a few Instagram accounts of stylish guys and see what they’re wearing. 

A great place to start is our Instagram.

FAQs

What should I wear in fall?

Start with a long sleeve t-shirt and add a light jacket like a bomber or a denim jacket. On bottom, try chinos or dark jeans and rock a pair of boots.

What are the best colors to wear in fall?

Keep your jackets neutral, like olive, indigo, or charcoal so you can wear them through winter. Add interesting fall colors like burgundy, mustard, deep purple, and burnt orange through long sleeve t-shirts and henleys.

Is plaid still in style?

Yes, plaid is still in style, though don’t wear a plaid shirt every day. It’s better to have one or two plaid shirts you reserve for casual days throughout fall and winter.

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