28 Stylish Fall Outfits For Men: How To Dress For Fall 2023
Fall's unpredictable climate can make getting dressed each morning tricky. But with our fall dressing guide you'll be prepared for any occasion, no matter the weather.
Summer is great and all, but there’s only so many shorts and T-shirt combinations you can wear before boredom sets in. Which is why we’re excited for the return of our fall wardrobes. With the cooler weather comes options: layers, texture, big coat energy and the return of denim. There’s more room for creativity with fall outfit combinations.
Your outerwear finally sees the light of day again, giving you the chance to play with silhouettes, while layers of shirts, overshirts, shackets and jackets add plenty of texture and depth. Colour palettes shift too, from the bright tones of summer to the more muted shades that better suit the changing forecast.
There are, of course, puddles and pitfalls to avoid, but with our handy guide to fall dressing, you’ll have it wrapped – figuratively, but literally as well.
How to dress for fall
Keep it tactile
One of the best things about fall fashion is the fabrics. Spring and summer clothes are limited in the texture department, with linen and cotton twill some of only fibres to offer anything tactile or visually interesting.
Fall, however, is much more touchy-feely. There’s corduroy, with its velvety sheen, the drool-worthy softness of cashmere and the mottled comfort of lambswool. Throw in trusty fallbacks like denim and tweed, plus trendy weatherproofing like fleece and waxed cotton, and suddenly, your outfit combos automatically feel more interesting.
Aside from tone and texture, fall dressing is all about lightweight layering. Neither too warm nor too cold, it’s a time of changeable conditions and temperatures – especially noticeable as you transition between interiors and the outdoors.
Dress with a few light layers – a tee, work shirt and raincoat, for example – and you can easily switch one or two of them out, depending on how warm you are.
Ready for rain
Fall weather is largely unpredictable, so it pays to be prepared. A waterproof top layer ensures you’ll keep your pride intact, should the heavens open, but it can also have other practical benefits.
Raincoats have breathable fabrics and handy pockets, plus they pack away easily if the weather breaks. And as a bonus, technical outerwear has never been more on trend.
Embrace a seasonal palette
Whereas summer is more suited to vibrant shades, fall dressing is all about muted, earthy tones. Think burnt oranges, deep burgundy, browns, greens and neutrals; colours that better represent the season and its transitional nature.
A fall colour palette is incredibly easy to wear too. The above tones all combine well with one another, making getting dressed foolproof, but they also work well with navy. Try a dark blue pair of chinos as a starting point, and add in a white tee, a sage green chore jacket and brown leather boots.
Men’s fall outfit inspiration
Smart casual fall layering
Dress it up with leather boots or keep things on the more informal side and finish with canvas high-tops.
For an alternative approach to fall casual dressing, try a sportswear-inspired look complete with technical cargo pants, hooded rain coat and running shoes, finished off with an oversized chore jacket.
Keep things minimal with a tonal palette or go for something more seasonally-appropriate with browns, reds and greys.
The knitted polo
An underrated choice, the knitted polo may be the fall piece you didn’t know you needed. Find one in navy blue and wear it with everything from denim jeans and desert boots to pleated chinos and classic sneakers.
While going tonal might be the easiest way to get dressed, it’s sometimes more interesting to throw a contrasting shade in there. That might be with your top half or, as here, in the form of trousers.
A crisp pair of khaki pants for example perfectly breaks up an otherwise all-green fit, consisting of a complementary varsity jacket, cardigan, beanie and suede moccasins.
Fall might be one of the most exciting times for tailoring. The colder weather means a whole heap of denser, textured and more interesting fabrics become viable options. Give the suit a new lease of life by trying a softly constructed take made from a herringbone or fleck wool, and combine it with a knitted polo and chukka boots.
Minimal fall dressing
Fall dressing doesn’t mean you have to go over the top with layering and colour palettes. Keep things simple and you’ll look just as good.
Stick to the classics
As always, you can’t go wrong when you stick to the classics. Menswear staples like raglan sleeve raincoats, crew neck jumpers, Oxford shirts, pale wash jeans and sneakers are the kind of clothes that never go out of style.
Combine them all together and you’ve got a timeless fall look that’ll look as sharp now as it will in a decade.
Keep it light
Light shades work surprisingly well for fall. You might think off-whites, beiges and neutrals better suited to summer, but pick out these tones in textured fabrics and they’ll look good any time of year.
Go for a check flannel overshirt for example and combine it with a lambswool crew neck and cotton twill pants and you’ll be sorted.
Black and brown
It’s a common misconception that black and brown don’t go together. Combine a dark brown jacket with black trousers and loafers and you’ll see that this ‘common style mistake’ is in fact no mistake at all. It helps if the jacket is a brown suede trucker which, providing it doesn’t rain, is ideal fall wardrobe fodder.
As far as versatile shades go, olive green has to be up there. The shade has plenty of militaristic connotations, but is essentially just a stylish alternative to navy. Wear it in the same way and pair it with grey and black, for a cool, easy casual look.
It might not sound like it, but wearing two shirts together is a surprisingly stylish fall menswear move. You just have to ensure the outer layer is an overshirt, and as such designed to be worn as more of a jacket.
You could keep things minimal and take a leaf out of the Scandinavian style playbook, or go bold with a louder check flannel shirt, depending on where the mood takes you.
Bolder, more vibrant pieces of outerwear are surely the easiest way to jazz up fall looks. Turn to textured designs and check patterns for your own attempts and you’ll find them easier to wear than you might first think.
Try the latter with an otherwise simple hoodie and chino combination and you’ll see what we mean.
Overshirts for the win
What more can we say about the overshirt? A staple layering piece that was practically made for the changeable weather of fall, it’s an item you won’t regret investing in.
Go for one in brown and wear it with virtually anything, from jeans or chinos through to tailored sweatpants and vintage running sneakers.
The wild one
You might think we’ve lost it for recommending a leather jacket for fall. But, providing it stays dry, it’s an underrated option. Invest in a good quality example and you’ll find the leather is surprisingly warm, especially when combined with a merino knit underneath.
You know the rest of the drill. Black jeans and leather boots make this a timeless look.
A staple look year round, double denim comes into its own during fall. The textured weave works best when you vary the tone of the top and bottom half.
A mid-blue denim shirt for example is an excellent pairing for a darker blue pair of jeans, instantly injecting your fall wardrobe with a slice of classic Americana.
Although typically a spring and summer staple, white pants are versatile enough to form the backbone of a stylish fall look. Whereas in the warmer months you might combine them with brighter hues, try pairing yours with neutral, muted shades like beige, grey and brown.
Keep it relaxed
It doesn’t matter the time of year, relaxed-fit garments are usually always the most comfortable. This is especially true of trousers, which can feel restrictive if too slim.
Go for a wider cut pant and you’ll immediately notice the difference. They’re just as easy to style, meaning they work with everything from Oxford shirts, crew neck knits and heavy wool outerwear, as proven here.
Blue and green should be seen
Blue and green works surprisingly well for fall, providing you stick to dark shades. Try a dark blue overshirt with an olive green pair of chinos, and keep the rest neutral with a grey crew neck and suede boots.
When it comes to staple fall pieces, the flannel shirt has to be up there. Made from soft wool and often coming in vibrant checks and varying colour ways, it’s a versatile piece that works as a mid layer or on its own over a crisp tee and chinos, as shown here.
Greys and blues
Grey and blue doesn’t just work with tailoring. The two shades are just as effective with smart casual ‘separates’, too. Think light grey bomber jacket, matching crew neck knit and navy blue tailored trousers, finished with classic white sneakers for a minimal take on fall weekend dressing.
Throwing on a vibrant coloured mid layer can transform an otherwise staid fall look. With the rest of the outfit simple, try a bright red or orange crew neck for a play point of difference.
Keep the whole thing contrasting or pick out the shade subtly elsewhere, in the check of your overcoat perhaps. The choice is yours.
It’s difficult to get navy wrong. The shade might just be the hardest working colour in menswear. From tailoring to the most casual of clothing, navy is classic, easy to style and complements every skin tone.
Try it for yourself with a smart casual look made up of a flight jacket, turtleneck and pleated trousers.
Skip the layers
As previously mentioned, fall weather is unpredictable. There will likely be occasions when outerwear isn’t required – perhaps on a particularly balmy day, or in the office.
For such times, keep it simple with a classic crew-neck sweat, tailored trousers and canvas high-tops, and you’ll be as stylish as you are comfortable.
Tailored casual wear
Some of the best clothes are those that are casual in design yet executed in a more refined, tailored way. Take the overshirt. Rooted in workwear and utilitarian clothing, it’s an inherently laid-back piece, but find one made from a cashmere blend and it instantly elevates it.
Combine it with a merino roll neck and high-waisted trousers and you’ll be both smart and sophisticated.
As the precursor to winter, fall is the ideal time to try out your heavier winter coats. But you’ll want to keep things light underneath so you don’t overheat.
That means pairing classics like a camel, double-breasted overcoat with a simple tee or polo, as well as lightweight chinos and sneakers.
A more obvious fall menswear move might be to combine knitwear with a lightweight jacket like a Harrington or bomber. But, for something more unconventional but no less stylish, why not double up?
A roll neck base layer works effortlessly with a smart knitted cardigan, especially if they both feature contrasting textures. Try a roll neck in merino wool and the cardigan in a ribbed cashmere blend and finish with tailored trousers and leather derbies.
If in doubt, go for a check overshirt. A fall essential, they can be dressed up with tailored trousers and loafers, or down with pale jeans and your favourite pair of sneakers.
When you’re struggling for outfit inspiration, it never hurts to turn to classic American style. Combine pieces like a varsity jacket with a letterman sweater, chinos, hoodie and retro running shoes and you’ve instantly got a cool, stylish fall look.