The 19 Essentials That Every Gentleman Needs This Fall

When you were a child fall meant new school gear to start the season off fresh.

It’s a little different for adults — no Trapper Keepers or freshly sharpened pencils — but freshness is still absolutely required.

To help you get set for the season, Business Insider put together a list of items that will put you in the right mind (and body) set to start anew.

We want you to look, feel, and think sharp, so this isn’t just about the clothes, people.

It’s about the gentleman.

Bomber jacket

Bomber jackets have that ultimate cool guy vibe to them, and they're one of those rare styles that's been all over the run way that also fits in your closet.

Get a great bomber jacket here for $US570, or a cheaper alternative for $US188 here.

Some dressed-up fall footwear

Paul Evan's Chukka in cognac, $US449

We're told that this autumn it's all about boots -- Chukkas, Chelseas and Oxfords (the pair pictured are from Paul Evans).

And as it gets colder (but not too cold and snowy) it's a good time to pick up some suede shoes. You can even design your own pair at Awl & Sundry

Read more about fall shoe trends here.

A leather portfolio

Unless you want to lose everything, definitely invest in a work bag.

Although messenger bags have been popular the last few years, we recommend you get a portfolio instead. Messenger straps can crinkle your shirt and suit -- and no one wants to look disheveled at a meeting.

You can get yourself a black leather portfolio from 3.1 Philip $US750 here at OWEN's online shop.

But if you must get a messenger bag, here's a cheaper option for $188.

Rain gear (jacket)

An umbrella alone is pretty useless. Stock up with some solid rain gear to protect all the other great stuff you own from the rain.

Get a high-end Patagonia for $US275 here, or a cheaper alternative for $US65 here.


If you live in Los Angeles, you can skip this one. But for those living in colder regions, unless you want the wind to peal your skin off, we recommend investing in a good scarf.

Stick with the classics, and get yourself a nice basic navy, grey, or even forest green one.

You can find a cashmere scarf for $US550 here, or stick with a more reasonable $US26 version here.

A navy blazer

The navy blazer dresses up any outfit and can act like as a jacket before it gets to cold. Take it with you everywhere.

You can find a great blazer for $US540 here or a cheaper alternative for $US75 here.


Bike to work before it's too cold out. Especially if you're someone who works long hours and don't have the time for a daily gym session. Plus, in the long run, you'll save money on commuting.

Get a solid bike for $US265 here.

A checkered shirt

Upgrade the spring and summer gingham shirt fad for some fall appropriate colours.

We recommend this great (and pretty cheap) $US45 Frank & Oak button down that you can get here.

Harry's shaving set

When it gets cold you may want to grow out your facial hair a little bit, but know that that means maintenance.

Invest in some quality shaving tools and your whiskers will look grown up, the way they should look.

You can get a $US15 or $US25 set from Harry's here.

The perfect navy sweater.

Yes, yes, we all know that you want to show off your Dartmouth degree with your seven-year-old, completely-falling-apart sweatshirt. But honestly, if you really want to impress people, try something a little more grown up.

It's impossible to look bad in a plain navy sweater. And it will keep you warm.

You can get a high-end $US300 navy sweater here or a cheaper alternative for $US90 here.


In that fall you'll want your eyewear to take on a more serious tone.

If you're not sure what will look good on you, try out something on the safer side like these $395 Barton Perreira sunglasses.

And if you're a bit more adventurous, check out these $425 ones.


Summer picnics are over, so it's socially unacceptable to play your blue tooth jam box. It's time to keep your music to yourself.

Check out this wireless pair from Bowers Wilkins. You can fold them up so that they're easier to carry around.

Pick them up for $US400 here.

A watch with a brown leather straps

The new hotness in menswear watch trends happens to be the brown leather strap. Think chocolate.

And bonus points, this kind of watch will look good even when brown is no longer 'trendy.'

We recommend picking up the Classic Bristol Daniel Wellington for $US229 watch here.

An serious book

Take a break from fantasy novels and pick up this gripping and smart nonfiction read for the fall.

The Bully Pulpit by Doris Kearns Goodwin chronicles the first decade of the progressive era -- a turbulent time, full of reform and change -- via the friendship of Theodore Roosevelt and William Howard Taft.

You can purchase a copy for $US17.47 here.


Glasses have been 'cool' the last few years, and the trend doesn't seem to be stopping anytime soon.

You could go with what these days seems like a mainstay, Warby Parker, or you could try Archibald Optics.

Archibald Optics lets you customise the glasses to your preference, without having to pay for the outrageous prices charged by other luxury glasses companies.

You can get a pair here for $US195 to $US300.

A good umbrella.

Here's a simple maths problem for you. What costs more: the 37 umbrellas you'll buy on a street corner for $US5 right as the thunderstorm is starting, or one quality umbrella for $US20 that will last for years?

You can get yourself a solid black umbrella for $US20 here.

Fun socks to add a pop of colour

Loud colours and patters are all over the place this season, but not ever guy is fashion forward enough to wear the trend everywhere.

Instead we suggest adding some flare to your look on your feet, with a cool pair of socks.

You can get the rocket ship ones here and the astronaut ones here -- both for $US28. And that's not enough, you can get some Jay Z approved socks here.

Chess set

There's more to great (read: gentlemanly) style than just a well-fitted button down.

Skip the candy crush, and learn how to play chess in your spare time. If that's not your thing, maybe give Stratego or Diplomacy a whirl. (The latter was the favourite game of both JFK and Kissinger.)

You can get a chess set here for $US12, Stratego here for $US25, and Diplomacy here for $US200.

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