The 19 Essentials That Every Gentleman Needs This Fall

Bomber jackets have that ultimate cool-guy vibe to them, and they are the rare style that has been all over the runway that also fits in your closet.

Get a great bomber jacket here for $570, or a cheaper alternative for $188 here.

We're told that this autumn it's all about boots — Chukkas, Chelseas, and Oxfords (the pair pictured is 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.

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

Although messenger bags have been popular the past 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 for $750 here at OWEN's online shop.

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

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 $275 here, or a cheaper alternative for $65 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 peel 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 $550 here, or stick with a more reasonable $26 version here.

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

You can find a great blazer for $540 here or a cheaper alternative for $75 here.

Bike to work before it's too cold out. Especially if you're someone who works long hours and doesn'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 $265 here.

Switch to darker liquors for the fall. And more specifically, whiskey cocktails.

You can always try the classics, like an Old-fashioned or Manhattan.

Or get a little adventurous. The Tipperary is like a Manhattan with Irish whiskey. Or try an Esquire (made with bourbon, Grand Marnier, orange and lemon juice, and bitters).

If your bar is stocked, try a Lion's Tail:

2 oz. bourbon
1/2 oz. pimento dram
1/2 oz. fresh lime juice
1 tsp. gomme syrup
1 dash Angostura bitters

And if you're totally clueless about where to go, check out BI's list of great speakeasy bars across the United States here.

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

We recommend this great (and pretty cheap) $45 Frank & Oak button-down that you can get here.

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

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

You can get a $15 or $25 set from Harry's here.

Yes, yes, we all know that you want to show off your Dartmouth degree with your seven-year-old, 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 $300 navy sweater here or a cheaper alternative for $90 here.

In the 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 Bluetooth Jambox. 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 $400 here.

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 $229 here.

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 $17.47 here.

Glasses have been "cool" the past 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 customize 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 $195 to $300.

Here's a simple math problem for you. What costs more: the 37 umbrellas you'll buy on a street corner for $5 right as the thunderstorm is starting, or one quality umbrella for $20 that will last for years?

You can get yourself a solid black umbrella for $20 here.

Loud colors and patterns are all over the place this season, but not every 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 rocket ship ones here and astronaut ones here — both for $28. And if that's not enough, you can get some Jay Z-approved socks here.

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 favorite game of both JFK and Kissinger.)

You can get a chess set here for $12, Stratego here for $25, and Diplomacy here for $200.

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