Men who do not want to put too much effort or time into their outfits can sometimes have a harder time dressing in the fall, when there are more factors contributing to the outfit. There are more layers to be had, and that can sometimes mean a little bit more complication.
However, dressing for fall can be very chic and flattering for men as long as you understand a few simple principles of layering. Here are some fall looks that are timeless and easy to throw together.
1. Charcoal Overshirt with Black Jeans
The black jeans are definitely one of the top staples I would recommend for men’s wardrobes. They work well in fall and winter as well as being casual. They look somewhat more polished than a lighter wash jean.
I also would say an overshirt like this can almost double as a jacket. This one here is not that thick, but the way that it is worn is almost like outerwear.
A peacoat is definitely a classic. I think we can all admit navy is a great color to invest in. Everyone looks good in navy, and it is one of those colors that is rich and feels timeless, like navy, burgundy, dark sage green, or maybe dark purple.
Navy pairs very well with this teal sweater. Teal brings a bolder pop of color, and if you have a bold piece like this in your closet and need to put an outfit together quickly, a navy peacoat over it is a simple, reliable match.
The simplicity of the timeless piece combined with the bolder piece, and then just classic jeans with a high-quality leather, or in this case suede, shoe, all adds up together to make a great outfit.
3. Camel Coat with a Merlot Turtleneck
Here is another rich color. We have merlot in this high-quality turtleneck. The turtleneck being of a quality wool or cashmere is not a necessity if you do not already own it. However, whenever possible, it is better to have higher quality items and fewer of them, which will make putting together outfits easier.
We have a camel coat. Camel is a great color to use in a more pared-back staple wardrobe. This goes with lighter colored outfits. This goes with darker colored outfits. Camel is a neutral that works well with almost everything. It also has an old money look.
4. Olive Field Jacket with a Denim Shirt
A field jacket is more casual, but it still feels refined. It is casual in a polished way. Here the denim shirt is also reading casual, but the fact that it’s a button-up, or a button-down, however you call it, especially the way that he has tucked it in, feels like he made a little bit of an effort.
Denim looks good on everyone. Field jackets look good on everyone. The fit does not matter as much. The denim shirt you can size up. It’s always better to size up than feel too constrained. The same goes for outerwear. It’s always better to have a little bit of room if you are not sure exactly which size you are.
The blue and the green here are both very natural, very classic colors that pair well. The shoes that he’s wearing are lace-up brown leather shoes. This is also maybe my top recommendation for footwear for men. It’s casual enough to wear every single day in the fall, winter, and spring. If you find a good pair of these shoes, they can last you for years and years. You can end up saving money compared to buying lower quality shoes and replacing them every couple of years.
Again, we have the navy. We have high-quality brown leather shoes. The navy, again, here is paired with a bolder color. The rust color is very much a fall classic. It makes you feel like Thanksgiving is coming, like the leaves are falling.
It feels cozy while still not being too bold. It definitely looks good on everyone. I like that these two colors together do not stand out too much because neither is too light or too bright, but it is still a colorful outfit.
6. Black Denim Jacket with Gray Wool Trousers
The black denim jacket is more of a bold choice because of its color. We often think of denim jackets as a blue denim jacket. In this situation, it looks like he’s wearing it to work, and a blue denim jacket would not be appropriate for work. I like the black denim jacket.
I do like that he is wearing gray wool trousers. Wool trousers are definitely more polished and more upscale than denim is. I think that the most casual piece in this outfit is the black denim jacket. However, the color is what is elevating it.
7. Chocolate Suede Jacket with Green Knitwear
Suede is very inherently fall. There is something that feels a little bit rustic about suede. It feels natural. It feels woodsy almost, even though it’s a higher quality material that requires a little bit more care than maybe a regular leather would.
Then there are the shoes that he’s wearing. Again, these shoes look good on everybody. They are very easy to pair with outfits that are more polished or professional, and then more casual outfits like the ones we’re seeing here. I think they just elevate whatever you are wearing in a not-so-over-the-top way.
The green knitwear is a nicer version of an athletic zip-up. If you were planning to wear a quarter zip in this style, a knitted version is worth the investment. Athletic wear only suits so many places, but knitwear can be worn almost anywhere.
8. Burgundy Harrington Jacket with Khaki Trousers
This is a little bit more of a vintage look. His khaki trousers definitely feel like a statement piece. I like that he even went a step further to tuck it in. He’s not afraid of dressing this up at all. It’s already bold with the blue and the raspberry burgundy Harrington jacket.
The stripe adds just enough pattern. It’s not a ton of pattern, but overall this is a refined, bold, bright outfit.
9. Plum Overcoat with All-Black Basics
The all black basics are timeless. It’s a base that we will see again and again. It’s so easy to use. It’s definitely the number one base that looks good on everyone. This is an easy thing to throw on, and it also looks chic no matter what is going on top.
You don’t even necessarily need a jacket on top, but in this situation he has chosen a more out-there choice of color. This is not a color that we’re seeing all the time, but it still feels very masculine combined with the all black base.
10. Gray Suit with a Mustard Knit
This is a bold color that is very much fall. Rather than being a rust orange, we have this mustard knit. When certain colors are so rich within themselves and so beautiful, they really do look good on everyone.
I think sometimes we pay too much attention to which colors look good on us. Does this wash me out or not? Sometimes a beautiful piece should be added to our wardrobe just for the fact that it is beautiful, and it will look beautiful on you no matter your skin tone. This is a great example.
I like that he paired it with a charcoal rather than maybe a black suit. The gray adds a little bit of lightness, where I think that the black would overpower the beautiful mustard color.
11. Tan Chore Coat with a Black Turtleneck
The chore coat is somewhat like the field coat. It’s ironically casual. It’s meant for chores, where the field coat is meant to be worn in the field. But in this day and age, when you have a collar on and it buttons up, or even zips with a collar, it feels very polished and you can get away with wearing it in more formal situations.
This looks like he is wearing it to work, or maybe in a creative space, and we see that his shoes are high-quality leather. They are lace-up boots. This is the same version of lace-up leather boot that we saw in the brown version. Here is the black version, which is a little bit less common but definitely can be used in the same way.
This outfit is simple on bottom. He added a little bit of interest by going with the gray-green trousers that he has rather than maybe a black trouser. I think that helps us correlate the pant color with the tan chore coat. It has a little bit of a flicker of brightness throughout the outfit rather than going with a completely black base.
12. Deep Purple Sweater with Dark Denim
Again, we have purple. This is a great way to wear purple, with these dark colors. Fall is an easy time to throw on a couple dark-colored elements like the dark denim.
We have a charcoal wool coat. A wool coat is definitely a great piece to have in your repertoire. It’s easy to throw on, and it looks professional even while wearing jeans.
13. Brown Leather Jacket with a Denim Western Shirt
This is a very fitted outfit. Everything is somewhat tailored and fitting him nicely. The jacket is by no means oversized. It has a little collar.
It’s nice to reach for a collared shirt and then throw a collared jacket on top. I think sometimes we can just go for one collar, but both of these together still look very nice.
Starting with the shirt, again we have this orange rust color that is so great in fall. It’s very much a fall color, but you can definitely wear it into the winter and even the spring. I could even see it in the summer, maybe with some neutral-colored shorts for a cooler summer day.
The color blocking here is so great. I would not have thought to add all of these colors into the outfit, but I think with the natural-looking leather boat shoes, it just makes sense. With the rich blue, the dark sage green, and then the orange Henley shirt, these are all very rich coordinating colors that make sense together.
15. Black Blazer with a Cinnamon T-Shirt
This outfit uses fairly casual denim. The jeans are slightly fitted, which makes them look more refined than a baggier cut. His shoes are also on the casual side. The blazer is what pushes the outfit toward something more formal and fashionable.
He is also wearing a t-shirt. This is a great color t-shirt for fall. I appreciate that he tucked in the t-shirt. That is a very simple way to elevate an outfit.
Together, the base is made up of very casual pieces: a t-shirt, worn denim, and then almost slipper-looking loafers. This turns from casual to sophisticated with the straight black blazer that he threw on top.
16. Green Bomber Jacket with Black Chinos
This is almost the opposite of the above outfit. We have a little bit more of a casual look on top. The bomber jacket is not necessarily athletic wear, but it’s more casual and outdoorsy, in an urban way, for outerwear. He’s wearing jeans, and it looks like a crewneck athletic wear top.
I like that he has a clean, not-too-worn white sneaker underneath. If he were to be wearing a more worn or maybe casual shoe with this, it wouldn’t necessarily feel polished. Together, with everything being clean and crisp despite being athletic or leisurely, it looks like a nice casual outfit to throw on when you’re running errands.
17. Maroon Corduroy Jacket with Blue Oxford Shirt
This is a lighter blue than we’ve been seeing. I appreciate the maroon. This is a color that looks good on everyone. It’s a nice, rich, old money color, especially paired with the oxford shirt.
We may think to reach for a white button-up shirt, but the light blue here actually makes the outfit have a lot more depth than if we were to have just a plain white or maybe a plain black shirt. It’s a little bit more interesting. The colorfulness of the top half is well balanced with the black and the brown of the bottom half.
18. Charcoal Topcoat with a Red Scarf
A bright red pop of color with an otherwise dark base. He has well-fitting dark denim here. His shoes are more formal than the pants.
Often the shoes are what is elevating the outfit. A sneaker here would make the outfit more casual, but because he is wearing a nice professional shoe, the look stays professional even with denim.
19. Denim Jacket with Brown Wool Pants
Rather than having the denim jacket be paired with jeans, he has chosen a wool pant here. Having something that is not a jean while wearing a denim jacket is usually a good choice. You can definitely decide to go with the full Canadian tuxedo with denim on denim. However, that is more of a statement and definitely slightly more casual.
A denim jacket itself definitely reads more casual, so if you want to play it up a little bit, go with a wool trouser or maybe a plain black trouser. I like the lighter-than-black base he has here. It’s a brown, and almost a khaki green on top. It feels casual and fall colored in a way that a black base would not.
20. Slate Quilted Jacket with Burgundy Chinos
Burgundy chinos are a little bit more unexpected. They are definitely more of a statement, however still a classic color.
The quilted jacket here is in a slate gray. It’s almost like a charcoal. It matches well with the rich colors that we often see in capsule wardrobes and old money wardrobes, like the navy and the burgundy.
21. Mustard Beanie with a Denim Overshirt
Here we have the perfect fall color palette. It’s mustard and then maybe a burnt orange, burnt red underneath, which we have in the hat and then the sweater that he’s wearing. Corduroy and denim are great fall materials, and you will get a lot of use out of each of these in your wardrobe.
The corduroys here are almost a utility cargo corduroy, which definitely serves a purpose. They are not the classic corduroy that we often find. They feel a little bit more hardworking and outdoorsy because of the extra pocket on the side and the utility loop that he has. We have the classic lace-up leather boots, which definitely will be versatile in many situations.
The base of the outfit here again is not denim, even though it is casual, because it’s a corduroy, but the denim shirt is offset by the darker, warmer colors throughout the rest of the outfit.
22. Cobalt Sweater with Gray Jeans
Cobalt is a little bit brighter than we often see in capsule wardrobes or in men’s wardrobes that are a little bit pared back, but this is an example of how to use a bright color without making the whole outfit feel too bold.
He has a gray base with the shoes and the jeans. The shoes here could easily be a white shoe. Even a brown leather shoe would look good. The light gray or medium gray jeans match well with blue.
Lighter gray and blue generally go well together, whether that be cobalt as we see here, or a baby blue, or a navy blue. Those all look good with various shades of gray, as we see on top with the darker gray jacket.
23. Dark Green Suit with a Brown Turtleneck
The suit being green is a very bold choice. It’s fun to choose different colors in formal wear, and it feels very fashionable for men. Dark green in this situation is pulled back with the brown turtleneck.
I feel like I would have expected him to be wearing a black turtleneck or maybe a lighter turtleneck, but the brown here makes the color palette fairly simple, matching his brown leather shoes and the brown pocket square that is popping out.
24. Black Parka with Copper Knitwear
The burnt orange, burnt yellow color palette is here again with the copper knit sweater that he’s wearing. The rest of his outfit is definitely casual. It’s more athletic in the parka, which serves a purpose here because it is raining.
The shoes that he’s wearing stand up well in the rain. A well-treated leather does not have to be avoided during harsher weather as long as it’s well taken care of, like the boots that we see here.
25. Heather Gray Hoodie with a Long Wool Coat
A hoodie underneath a collar is a very timeless yet unexpected combination that looks good on everyone. Here it’s a hoodie, but it can also be a zip-up hoodie or maybe a quarter zip with any sort of collared jacket.
The long wool coat definitely feels more polished, especially since he has a cargo pant on. If he had any other jacket on, it would feel more casual, but the long wool jacket is pulling everything together.
This outfit also uses navy and gray, which pair well. The green adds a more autumnal, outdoorsy note. The black leather sneakers look polished. A white sneaker would also work, but the black grounds the outfit alongside the navy.
26. Burnt Sienna Shirt Jacket with Black Trousers
Burnt sienna is a great fall color. It feels warm and cozy. The shirt as a jacket is a nice addition when it’s not too cold but also not very warm outside. This can be in a warm wool. It could also be in a cotton, something that’s cozy but a little bit structured.
Black trousers are what is making this appropriate for work. He has dress shoes on, black trousers, and then this is a gray turtleneck. It could also be a black turtleneck, or maybe even a cream turtleneck would work here.
The rich colors are doing all of the work here. This outfit definitely feels casual. He almost intentionally tucks in half of the shirt. I believe that’s called the French tuck, where just one portion of the shirt is popping out. It feels a little bit intentional and a little bit more fashionable because he did that.
It’s showing off the belt, which is completing the grayish blue base that he has on bottom. We have a lighter navy rain jacket that is coordinating with the green and blue plaid shirt.
Green and blue, then the dark green, dark blue, and the dark red knit cap: we’ve been seeing these colors throughout this whole wardrobe. I think it goes without saying that investing in these colors, even just a few, is worthwhile, because they can mix and match so easily with each other.
28. Espresso Blazer with Sage Knitwear
This is a lighter version of the green we’ve been seeing, but the same navy that matches well with the green. It’s not matchy in that sense, but it matches in that it coordinates well.
For brown accessories here, we have the brown blazer, which is completing the more formal look, and then a casual but still upscale suede leather loafer, which is not completely matching the brown leather belt. But overall, this is a smart, chic look, which is easy to put together for a more formal dinner, maybe at someone’s house.
Many of these outfits rely on wool sweaters and coats. Woolmark’s washing guide recommends washing wool knits inside out on a wool or delicates cycle and drying them flat, and its storage guide suggests storing them folded with cedar blocks at the end of the season.
The Building Blocks
Two basics that work under and around most of these outfits.
- Men’s Regular Fit Oxford Shirt. The blue Oxford from #17, which also layers under most of the sweaters on this list.
- Men’s Genuine Leather Belt. A plain brown belt for the chinos and trousers in #5, #8 and #19.
About the Author
Allena Rissa
Founder & Editor
Allena Rissa is the founder and editor of The Better Fit. She has been writing about clothes since she was twenty-two, and for nine years she has been the one dressing her husband, her kids, and herself for family photos, fall weddings, work conferences, and Christmas cards that had to land. On the site she covers five pillars: Her Style, His Style, Together, Occasions, and Foundation, the bras and fit mechanics that started it all. Her advice has been featured in Cosmopolitan, Better Homes & Gardens, Insider, and NBC.