The Five Essential Men’s Jackets for Fall

In a range of styles and price points

By The Editors

The Five Essential Men’s Jackets for Fall
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26 September 2016

According to our calendar, the time is precisely fall, and that means one thing:

It’s officially jacket season.

So, before the nip in the air gets noticeably more … well, nippy, let’s get you kitted out proper.

From denim jackets to bomber jackets, here are the five essential pieces of outerwear every Chicagoan should consider adding to his arsenal — each in a range of style and price points, and ready for the uncertain climes ahead.


Photo: Taylor Stitch
The Denim Jacket
It’s a jacket that simply never goes out of style. Mostly because it goes with everything. Light wash denim is having a moment, and you’ll never go wrong with a classic Levi’s Trucker jacket. Or better yet, go raw denim with the Long Haul Jacket from Taylor Stitch and do the work yourself.

GET IT HERE: Levi’s ($90); Taylor Stitch ($188); Steven Alan ($265)


Photo: Independence
The  Blazer
Used to be we reached for more structured jackets in the fall, but these days the casual soft-shoulder blazer is a go-to look that can be acceptably worn all year round. Do, however, keep in mind texture. You still want something seasonal: wool, tweed and corduroy all prove to be adequate for fall when unexpected dips in the weather are all too common.

GET IT HERE: Kit & Ace ($298); Engineered Garments ($495); Billy Reid ($690)


Photo: Alpha Industries
The Bomber
Google says you should own one, and we agree. Plus: is there anything more masculine than a bomber? No, sir. There is not. If you wanna go classic with all Army-Navy fixins, look for anything that says “MA-1,” the official specification number most brands have adopted. Otherwise, keep it minimal.

GET IT HERE: Alpha Industries ($150); Adidas x Wings + Horns ($355); Tim Coppens ($695)


Photo: Reigning Champ
The Coach Jacket
There’s something about a coach’s jacket that agrees with these parts. Maybe because it’s inherently sporty, and Chicago is a sports town. Or perhaps it’s because it’s possibly the easiest jacket to pull off, no matter the wearer’s style. Either way, it’s the perfect no-fuss jacket that’ll up your style in any situation.

GET IT HERE: Saint Alfred ($68); Reigning Champ  ($230 CAD); Bleu De Paname ($185)


Photo: Schott NYC
The Leather Jacket
A nice leather jacket is an investment. Sure, it’s something you won’t necessarily wear every day, but it’s something you’ll wear for days when you need an edge. It doesn’t get more iconic than Schott’s Perfecto motorcycle jacket. We love it not only because it’s tough, but because it can be dressed up or down, and can be worn by anyone, no matter the age or style.

GET IT HERE: Schott NYC ($750); Sandro ($1,195); RRL ($1,800)

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