5 Best Jackets To Keep You Looking Stylish (How to Wear & Where to Buy)9 min read

There are many types of jackets for sartorial minded gents to experiment with, and (in my opinion) these are the best jackets for men that you’ll definitely want to know about in 2021.

5 Best Jacket Styles For Men | GENTLEMAN WITHIN

I’ve written extensively about various types of men’s jackets, namely two classic styles, the denim jacket and the bomber jacket.

In this article I break down the 5 best fall and winter jackets for men, how to wear them (style guide) and where you can buy them at different price points.


10 BEST JACKETS for Stylish Guys | Men's Style & Fashion Inspiration

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These casual jackets are my top 5 men’s jacket styles that I feel are equal parts seasonally appropriate, versatile and stylish.

Let’s get to it.

1. The Bomber Jacket

Tan Suede Bomber Jacket Outfit at Penns Landing

MA-1 Bomber Jacket History
B-52 Crew 644th BS, 410th Bombardment Wing, 1966

The bomber jacket dates back to the 1950s and has its roots firmly imprinted in the European and United States military.

There are many varieties of the bomber jacket, from the ‘letterman’ jacket, popular among high-school teenagers to the baseball varsity bomber jacket. Then there’s of course the iconic Alpha Industries bomber. These jackets are typically distinguished by a ribbed collar, waistband and cuffs.

Today the bomber jacket is one of the most iconic fashion pieces in pop culture, worn by celebrities, athletes and regular civilians.

Where To Buy A Bomber Jacket

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Budget Options (Under $100)

Mid-Level Options ($100-$500)

Grail Options ($900+)

How To Wear A Bomber Jacket

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The bomber jacket is one of the more popular men’s jackets and is best suited for the spring and fall seasons when it’s not too hot or cold.

In my opinion a bomber jacket shouldn’t be too loose or baggy. Sure you can layer a piece or two (t-shirt and sweatshirt or hoodie) underneath, but anything more than that adds too much bulk.

Additionally, a suede or wool bomber jacket can work with monochrome athleisure looks. Or a slightly more dressy look, for example, over top of a button down and crew neck sweater.

And finally, bomber jacket outfits lean on the casual side and look great with trim and tailored dark wash jeans. Check out this review of the great lightweight Everlane bomber jacket.

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5 ESSENTIAL JACKETS this Fall & Winter for Short Men (Best Jacket Styles to Wear Now)

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2. The Leather Jacket

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Leather Jacket Outfit at the Sydney Opera House

A leather jacket is the grail piece of all the jackets on this list. The motorcycle (or biker) leather jacket particularly, is a rakish as it gets.

It’s one of those types of jackets that when confidently pulled off, will surely channel those James Dean bad boy vibes with or without the bike.

ASOS Barneys Leather Jacket Review (Best Leather Jacket Series) | GENTLEMAN WITHINRelated Article: You might like this ASOS Barneys Leather Jacket Review.

In addition to the motorcycle jacket, there’s also the racer, and bomber jacket variety as well. And if it’s thick enough, it can serve as a warm winter jacket.

James Dean Triumph Motorcycle Leather Jacket
James Dean riding his Triumph motorcycle, 1955

Leather Jacket Brands To Look At

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Budget Options (Under $300)

Mid-Level/Grail Options ($300+)

How To Wear A Leather Jacket

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Should Guys Wear Leather Jackets?

The beauty of leather jackets are how many different varieties there are. More than likely you’ll be able to pick a style that resonates with your aesthetic.

Motorcycle jackets typically found in black can be found in brown as well. With a black biker jacket, you’ll want to keep the rest of your look dark. An all black outfit, top to bottom keeps things casual and streamlined.

AllSaints Milo Biker Jacket Review (Best Leather Jacket Series) | GENTLEMAN WITHINRelated Article: You might like this AllSaints Leather Jacket Review.

Meanwhile a brown leather jacket is prime to be dressed up with button up and necktie. Even still, these are rakish looks with a touch of refinement and complete masculinity. The answer is definitely, yes.

Related Video:

TOP 5 BEST JACKETS All Guys Need In Their Wardrobe & How To Style Them

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3. The Denim Jacket

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Elevated Denim Jacket Outfit At Hotel

Robert Redford Denim Jacket
Robert Redford, riding with Lauren Hutton in the movie Little Fauss and Big Halsy, 1970

The denim jacket, also called a jean jacket and trucker jacket (popularized by Levi’s) is a classic style that’s been around since the late 19th century.

This vintage staple has since become an iconic piece in American fashion. If anyone tells you that denim jackets aren’t in style, they’re wrong because the denim jacket is a timeless jacket style.

Whether it’s dark wash, mid or light wash with vintage fades, the denim jacket remains a timeless staple not just in American fashion, but around the world.

Where To Buy A Denim Jacket

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Budget Options (Under $100)

Mid-Level Options ($100-$300)

How To Wear A Denim Jacket

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The denim jacket is a fall favorite because it’s inherently casual and looks great with dressed down, relaxed outfits, but also looks great dressed up with a turtleneck or a necktie for example. It’s also one of my favorite summer jackets because of the wide variety of shades from dark to light.

Denim on denim of course is a bold move, but it can be done. Ensure there’s enough contrast between the shades of denim to avoid a Brokeback mountain vibe or if you’re going to match denim shades, stick with darker wash and a slim fit as it’s more of an elevated aesthetic. I feel like light wash denim on denim looks really tacky.

Another great denim jacket look is to pair it with a hoodie and distressed jeans for a more youthful, devil-may-care attitude.

Finally, denim jackets work great as a mid-layer in the winter time, worn under outerwear like a parka or coat that’s roomy enough for it to fit comfortably underneath.

Quick note: If you’re enjoying this article on the 5 best jackets for men, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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4. The Harrington Jacket

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Smart Casual Harrington Jacket Outfit At Bryn Mawr College

The harrington jacket also known as blouson, and originally called the Baracuta G9, was popularized by Elvis Presley in the late 1950s.

It’s a lightweight, waist-length jacket made of cotton, polyester, wool blend or suede. A distinguishing feature of the Harrington jacket is its slanted flap pockets and tartan/checkerboard-patterned lining.

Olive and especially navy, are my two favorite colorways for the harrington jacket.

Elvis Presley Baracuta G9 Jacket
Elvis Presley wore the Baracuta G9 jacket in the movie King Creole in 1954

Where To Buy A Harrington Jacket

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Budget Options (Under $100)

Mid-Level/Grail Options ($100-$300+)

How To Wear A Harrington Jacket

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This underrated menswear staple is perhaps my favorite of the 5 jacket types in this article. I love it so much because it’s casual, lightweight and just ultra-stylish.

Feel free to wear a harrington jacket with everything from casual sneakers to rugged boots. Layer it over top of a button down shirt, polo or sweater. It’s just as appropriate when paired with a tie.

You simply can’t go wrong with a harrington jacket in the spring and autumn, even into winter season.

Related Video

THE 6 BEST SPRING & SUMMER JACKETS Every Guy Needs | Spring Style Lookbook | Men's Fashion 2019

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5. The Field Jacket

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Autumn Americana Field Jacket Outfit at Tyler State Park

The M-65 field jacket is standard issue military gear, evolved from the M-51. It sports multi-pockets, an olive-green color and was designed for war. It’s been worn by American soldiers in Vietnam to Arnold Schwarzenegger on the big screen.

This iconic military jacket gets major functional points, heritage points and of course style points. With a timeless, vintage design, the field jacket is every bit as American as blue jeans.

Field Jacket History
The field jacket spans pop culture and military history to the silver screen | HiConsumption

Where To Buy A Field Jacket

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Budget Options (Under $200)

Mid-Level/Grail Options ($200+)

How To Wear A Field Jacket

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Last, but not least, the field jacket is the only jacket style on this list that drapes a little bit longer. All of the other jacket types are cropped pretty short for a casual and modern aesthetic, whereas the field jacket, while still casual is markedly a rugged jacket.

The field jacket’s casual, loose and free-flowing aesthetic calls for endless layering combinations. Wear it over a thicker hoodie or cardigan sweater. Or dress it up with a button-down, necktie combo.

Additionally you can pile on the layers by throwing on a solid scarf or make the unexpected style move of wrapping your shirt around your waist. The field jacket’s never looked so civilian.


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I hope this editorial helped explain why these 5 jacket styles are essential for all men. And that you got styling inspiration from all the curated looks. I purposely omitted certain styles like the double breasted pea coat because I see it more as a winter coat.

But feel free to reach out if you have any jacket recommendations to add to the lists.

Editor’s Note: This post was originally published on November 21, 2018. Updated for accuracy, comprehensiveness and the addition of a buying guide.


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  1. Matthew C. Kirk says

    This article is so amazing. These days leather jackets is so popular in world wide. I like Denim and Cafe Racer Jackets.

  2. Rishabh limestays says

    Great article.Thanks for sharing the blog because in today’s time leather jackets are in trend and its necessary use for everyone in many different varieties and patterns.Keep up the good work.

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