• David Connolly

Cool Jackets For Men That Will Never Go Out Of Style

Updated: May 29

The right jacket will make or break an outfit. It is a stamp of your signature style regardless of what you’re wearing underneath. Jackets are also one of the most versatile parts of your wardrobe. Unlike ‘seasonal’ purchases, middleweight jackets are layering essentials that are guaranteed to get tons of wear. The best part? These classic jacket styles have been around for forever—exuding effortless cool factor but timeless elegance. Whether you're investing in a bomber, a raincoat, or a leather jacket, these toppers will be fashionable year round, for years to come.

Cool Jackets That Will Never Go Out Of Style

Cotton Bomber Jacket $87.50 USD


Bomber jackets have become a menswear staple. This option has an effortless, minimal aesthetic and is made with the highest quality sustainable fabrics. Your search for the perfect bomber jacket ends here.

Cow Irish Cropped Leather Jacket - $313.25 USD

The Kooples -

Nothing adds a little edge like a motorcycle jacket. It’s the ultimate day-to-night menswear piece. It looks just as great with a dress shirt and trousers as it does with a t-shirt and jeans. This one from The Kooples is accented with hardware, but the cropped waist and sharp tailoring keep things refined.

Reversible Harrington Jacket - $124.00 USD

Scotch & Soda -

Imagine the classic Harrington jacket. Now, literally, turn it inside-out. Scotch & Soda’s take on a Harrington jacket looks like the classic—a roomy silhouette, light camel color, and ribbed hem and cuffs—the only difference being that it’s reversible. The inverse jacket has a checked pattern, striped cuffs and a logo patch. Classic or cool? Depends on your mood.

Color Block Tricot Jacket - $89.00 USD

Ben Sherman -

A track jacket is the quintessential casual layering piece for warm weather. This variation from Ben Sherman is a slightly elevated, more tailored cousin of the track jacket you’d wear to the gym. It is perfect for weekends, running errands or anytime athleisure calls.

Maldini Corduroy Overshirt - $195.00 USD

Reiss -

Corduroy is having a moment. We hope everyone else is as thrilled about that as we are. A corduroy shirt-jacket is the perfect answer to those pesky not-too-warm but not-too-cool spring and fall days. An unexpected color like oatmeal gives this retro overshirt a delightfully modern twist.

Trucker Jacket - $98 USD

Levi's -

There are few jackets as iconic as Levi’s denim trucker. If you own a jean jacket, it was probably inspired by this one. Sometimes, there’s nothing quite like the original.

Synchilla Snap-T Pullover - $98.00 USD

Patagonia -

Let’s be honest: fleece jackets are not the most exciting. Let’s be honest again: we all have one (or many) anyway because they’re so darn comfortable. Patagonia's signature pullovers give this casual favorite a cool twist with bold patterns.

Stockholm Raincoat

Stutterheim -

This Swedish raincoat is the ultimate marriage of form and function. Stutterheim coats are made by hand using rubberized cotton, snap closures and cotton drawstrings, and come in a wide variety of striking colors and patterns. Never before has a raincoat worked so hard to keep you dry, yet looked so good doing it.

Author: Heath Owens

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