What to Wear in The Fall? (Men Wardrobe Must Haves)

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What to Wear in The Fall?

Here’s my list of men’s must have items that will keep you both looking fashionable and comfortable this fall.

Let’s begin with the most significant menswear components.


Typically, I recommend wearing a pair of sleek, fashionable, fitted trousers.

But if you want to mix things up in fall, I’d suggest choosing a pair of relaxed-fitting wool trousers.

We typically associate wool with being warm and itchy, but I can promise you that relaxed wool clothing is actually breathable.

Actually, the elastic waistband on my current favorites makes them even more comfortable.

The most versatile shades are black and navy, so I’d recommend getting a pair in either color, or maybe one of each.

The trick to pulling off this type of pant when it comes to fit is to achieve a balance between relaxed and fitted.

Making sure that the clothing you’re wearing on your upper body, such as a t-shirt or sweater, fits your torso properly will help you achieve this. A slimmer fit will help balance out the relaxed fit of the pants.

Corduroy Pants

Corduroy pants, formerly the sole domain of your grandfather and hippies, have experienced a significant resurgence in recent years, and in my opinion, are the ideal fall pant.

Along with being quite comfortable, the fabric also looks great when matched with more straightforward items on your upper half, like a tour jacket and t-shirt.

If it’s your first pair, stick to colors that are more associated with fall, such as brown, burgundy, dark green, or even mustard if you want something a little more vibrant.


Next up we have a pair of pants that looks just as fantastic in the fall as it did throughout the summer months – chinos.

The most functional pair of pants a man can own. They are a stylish neutral between smart and casual that flatters all body types.

As we enter the fall, some retailers may offer thicker chinos for an added bit of warmth. You can also spice up your wardrobe by adding colors like gray, brown, dark green, and burgundy to go with the season.

Otherwise, sand and navy are undoubtedly the most versatile colors that you should choose if you haven’t already.

Dark Wash Jeans

Let’s talk about the pair of pants that you almost likely saw coming, dark wash jeans.

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You’ll need these in the fall, just as you would in the spring, summer, and winter.

You should absolutely choose a pair of dark wash or indigo jeans without any contrasting stitching as we are moving away from brighter colors.

This will provide a neat, fashionable, and professional look that will go with whatever you pair them with.

Black and gray are your other color options, and they also look great in the fall and winter, providing your wardrobe is already stocked with dark wash jeans.

Crewneck Sweater

Next, we have the crewneck sweater, another classic piece of menswear. When the weather starts to turn a little cooler, it’s the ideal transitional piece.

The crewneck sweater is an incredibly fashionable and functional layering piece.

Make sure you understand the fundamentals when it comes to color. I’m referring to dark hues like navy, charcoal, and black.

Once you have those, you can definitely go out to other fall colors like brown, tan, camel, dark green, and burgundy.

However, some of these colors can be a little challenging to wear, so be sure to pick one that matches your skin tone.

With some wool trousers and dress shoes, your sweater can be simply dressed up. Alternately, opt for a more casual look by wearing items like jeans, chinos, and sneakers.

Sweaters undoubtedly look great when draped over a basic t-shirt, but if you’re a lover of wearing collared shirts, then I’d recommend going for a v-neck sweater instead.

Button-down Shirt

Speaking of collared shirts, a casual button-down shirt is a fall must-have that will quickly update your go-to t-shirt and jeans look.

This is a great go-to for your everyday uniform, whether you choose the traditional Oxford in white or light blue or even more casual shades like dark green, navy, or burgundy.

When it comes to the kind of fabric for your button-down shirt, you have a variety of choices.

You can choose from cotton, flannel, or basic Oxford cloth. You can choose between patterns and solid colors based on your personal preference.

The appeal of the casual button-down is that it goes well with any of the pants I previously suggested for a laid-back but polished appearance.

You can also try rolling up the sleeves and doing a partial tuck by tucking the front of the shirt into the front of your pants. You now have a look that is quite stylish as well as being extremely comfortable.

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And when it starts to get a little chilly, add a jacket for a stylish ensemble that is smartly layered.


Speaking of jackets, the overshirt, also known as a shirt jacket or a shacket, is a heavier version of the casual button-down that you should consider wearing.

This fashionable piece is ideal for fall and can be worn unbuttoned or with a t-shirt for a more casual but polished appearance.

You can choose from selections in both solid and flannel-style plaid colors.

I strongly recommend avoiding neutral colors and opting instead for the more earthy fall suited tones like dark greens, camel, burgundy, mustard, and gray because these casual shirts are considerably more suitable than a jacket.

Bomber Jacket

While we’re talking about jackets, the bomber jacket has to be the one new piece of apparel you add to your wardrobe this fall.

Why are bomber jackets so appealing to me?

It basically comes down to the fact that they complement everything and just look great on every man, regardless of his age or body type.

In addition to this, bombers have the ability to keep everything looking proportional by breaking up your body in a manner that is really attractive.

I’d recommend updating your current wardrobe for the fall by including a bomber jacket in wool or suede.

Winter and fall are the seasons of textures, so if you want to go all out for fall, stick to burgundy, olive greens, and neutral shades of gray and brown.

Trucker Jacket

The trucker jacket, which is the next item on my list, is a great choice if you’re looking for something a little more rugged.

This traditional garment has a masculine style, but if you believe you have to stick with denim, think differently.

I would recommend investing on a soft and buttery suede version if you have the money.

The fit on truckers is designed to be tighter than on bombers.

I must tell you that this particular type of jacket will not flatter you if you are a bigger guy who also happens to be on the shorter side.

In most cases, if you have to choose a larger size, the length and the sleeves will be too lengthy to fit your torso and arms’ width and length.

Yes, you could get alterations done, but they would be expensive and, to be honest, not worth it, especially because there are alternative jacket types that will look fabulous on you, like the bomber jacket or the next pick on my list.

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Chore Jacket

This jacket is the ideal compromise if you find sports coats to be a little too formal and conservative. It will give your outfits a more casual feel while still boosting your entire look.

The best thing about chore jackets is that they can be worn during the day as well as at night. They also make great layering pieces for people who are overweight in the upper body.

This is because the chore jacket aids in breaking up your body vertically, which has a great slimming effect.

However, keep in mind that if you are one of those bigger men, you should refrain from zipping or buttoning any jacket. This will simply make you look larger and prevent us from seeing any of your fall-inspired layering.


Fall marks the beginning of boot season, which is one of my favorite aspects of the season.

A pair of Chukkas or lace-up boots, especially made of leather or suede, should undoubtedly be your preferred footwear choices.

If you wear boots frequently, you probably already know to go for a dark brown, tan, or black tone because these are the shades that will blend with the rest of your outfits the easiest.

However, if this is your first pair, a medium brown pair is the best option.

Since you don’t want to see the damage that water might cause to these things after you’ve paid for them, suede should only be taken into consideration if you live somewhere with little to no rain.


I usually would recommend a pair of white leather lace-up low-top sneakers when talking about footwear for your fall wardrobe.

However, I’ll presume you already own a pair of those.

My suggestion is to switch up your sneaker collection by choosing some low tops made of leather in either black or brown.

Choose black if you typically wear more black clothing. But if not, then definitely go for the ever trustworthy brown.

If you’re having trouble deciding, I suggest treating yourself to the essential piece of any man’s wardrobe and purchasing both to update your shoe collection with these incredibly adaptable colors.

men's fall wardrobe must haves

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