How to Wear a Bomber Jacket | 5 Ways Lookbook

This one is for the guys who want inspiration on how to wear the ever versatile bomber jacket.

How to Wear a Bomber Jacket: 5 Ways Lookbook | GENTLEMAN WITHIN

A few articles ago, I reviewed the Alpha Industries MA-1 Skymaster Flight/Bomber Jacket, and included a lookbook video, but only featured one outfit. And so I want to expand upon the review and show 4 additional ways to style a bomber jacket. In addition to the Alpha Industries bomber, I’ll also be styling a tan, suede bomber jacket which is highly versatile in its own right.

But enough talk, let me show you.

HOW TO WEAR A BOMBER JACKET

Take a look at and get inspired by these 5 different ways to rock a bomber jacket.

LOOK 1: OREO BOMBER


SHOP THIS LOOK—Jacket: Asos (on a budget) | Sweater: Asos (similar) | Boots: Thursday Boots | Jeans: Levi’s

This one gets its name from friend and fellow style blogger, Carl Murawski of New England Style Consulting. It’s brown on the outside with cream in-between, “like an Oreo!” he said.

The ‘Oreo Bomber’ may seem stuffy for Summertime, but it all depends on the weather. I’m in the camp that says ‘yes’ to wearing suede Chelseas all year long. And white is one of my favorite color pants to wear in warm weather. The suede bomber is mid-weight, so it’s perfect for when the weather dips. But what about that sweater? It’s fine as long as it’s a lightweight fabric.

Oreo Bomber 1
SHOP THIS LOOK—Jacket: Asos (on a budget) | Sweater: Asos (similar) | Boots: Thursday Boots | Jeans: Levi’s | Watch: Timex | Watch Strap: Cheapest Nato Straps | Sunglasses: Sunny Rebel via Gentleman’s Box | Bracelet: Taft

WHY IT WORKS:

Brown pairs exceptionally well with a myriad of colors, white and cream included. The color of the jacket and boots are basically identical which helps to create harmony. And the textured sweater adds visual interest to an otherwise very simple outfit.

Oreo Bomber 2
SHOP THIS LOOK—Jacket: Asos (on a budget) | Sweater: Asos (similar) | Jeans: Levi’s | Watch: Timex | Watch Strap: Cheapest Nato Straps

WHEN TO WEAR IT: Spring and Fall seasons 40ºF to 55ºF.

LOOK 2: JETSETTER BOMBER

SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Shirt: Tailor Store | Shoes: J. Crew | Chinos: Uniqlo

This is how I’d rock the bomber jacket to travel. It’s the 3 C’s menswear trifecta—casual, cool and comfortable. The deep purple and gray flannel button up in a gingham pattern complements the bomber jacket’s casual aesthetic. This cool outfit is complete with well-fitting navy chinos and casual sneakers, both versatile styles and colors.

With this smart look, you’ll get all the style points, and be ready to take flight in style.

Jetsetter Bomber 2
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Shirt: Tailor Store | Shoes: J. Crew | Chinos: Uniqlo | Watch: Timex | Watch Strap: Cheapest Nato Straps | Sunglasses: Sunny Rebel via Gentleman’s Box | Bracelet: Taft

WHY IT WORKS:

This color scheme is packed with harmonious and complementary colors. On top of that, chinos and sneakers go well together, especially since they’re navy and white, which goes with virtually any color. The reason I got this bomber jacket in olive/gray is because of the versatility.

Finally, the untucked button up, enhances the bomber jacket’s casual style and appeal. Throw on some summer shades and you’re ready…you Jetsetter, go getter, you.

Jetsetter Bomber 1
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Shirt: Tailor Store | Shoes: J. Crew | Chinos: Uniqlo | Sunglasses: Sunny Rebel via Gentleman’s Box

WHEN TO WEAR IT: Spring and Fall seasons 45ºF to 65ºF.

LOOK 3: REFINED BOMBER

SHOP THIS LOOK—Jacket: Asos (on a budget) | Shirt: GAP (similar) | Jeans: Banana Republic | Shoes: Thursday Boots | Tie Clip: The Tie Bar

This third look I’m calling the ‘Refined Bomber’ because a suede jacket naturally lends itself to being dressed up. And so I threw on a dotted navy, knit tie and tan double monk strap shoes to easily achieve refined status.

Alternatively, I could loosen up the tie and reposition the tie clip so that it’s angled for what I’m going to call the ‘Sprezza Bomber’ aesthetic.

If you don’t know, sprezza is short for sprezzatura (spretsəˈt(y)o͝orə/) which is defined as “a certain nonchalance, so as to conceal all art and make whatever one does or says appear to be without effort and almost without any thought about it”.

Sprezza Bomber Outfit 1
SHOP THIS LOOK—Jacket: Asos (on a budget) | Shirt: GAP (similar) | Jeans: Banana Republic | Shoes: Cole Haan | Tie Clip: The Tie Bar | Watch: Timex | Watch Strap: Cheapest Nato Straps | Sunglasses: Sunny Rebel via Gentleman’s Box

WHY IT WORKS:

Just as the suede bomber can be dressed down with a plain white tee, it can be elevated with a button up and tie, tie bar combo. And the tie is no ordinary tie, it’s a dotted knit tie, which gives this refined look an air of casualness.

As for the shoes, the double monkstrap is simply badass. There’s a reason it’s on my list of essential shoes for men. Dub monks are the most stylish shoe that I own. This pair in a cognac/tan/walnut, whatever you want to call it, always gets attention and compliments. On top of that, a crisp pair of slim fit, dark wash denim complements it well.

Sprezza Bomber Outfit 2
SHOP THIS LOOK—Jacket: Asos (on a budget) | Shirt: GAP (similar) | Jeans: Banana Republic | Shoes: Cole Haan | Tie Clip: The Tie Bar | Watch: Timex | Watch Strap: Cheapest Nato Straps | Sunglasses: Sunny Rebel via Gentleman’s Box

WHEN TO WEAR IT: Spring and Fall seasons 50ºF to 65ºF.

LOOK 4: RUGGED BOMBER

SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Hoodie: Asos | Jeans: Levi’s (similar) | Boots: Thorogood | Hat: New Era

I don’t rock fitted caps as much as I used to, but whenever I don’t feel like styling my hair, it’s my hat of choice, up there with the now trendy dad hat. I feel that a hoodie and fitted are a good match. Combine it with the Alpha Industries bomber jacket, distressed Levi’s with a rusted fade and some brown work boots and you’ve got the ‘Rugged Bomber’ on lock.

If you do try this look, make sure the hoodie is thin. Preferably thinner than the one I’m wearing, which is as thick as you’ll want to go.

Hypestreet Bomber 2
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Hoodie: Asos | Shirt: Asos | Jeans: Levi’s (similar) | Boots: Thorogood | Hat: New Era

WHY IT WORKS:

Anytime you’re rocking a hoodie with a jacket, it’s going to be a really casual look. The distressed jeans and work boots add to the rugged aesthetic. This isn’t a look I’d normally wear, but it looks like I belong in this particular environment. In the context of the environment, I’m appropriately dressed, whereas the ‘Refined Bomber’ seems too dressy for this place.

 

Hypestreet Bomber 1
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Hoodie: Asos | Hat: New Era

WHEN TO WEAR IT: Spring, Fall and Summer seasons 35ºF to 55ºF.

LOOK 5: HYPESTREET BOMBER

SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Sweatshirt: Burnside (similar) | Boots: Thursday Boots | Jeans: Levi’s | Bracelet: Armoir Fashion via Gentleman’s Box | Flask: Labara

This one is a play on the hypebeaster movement/culture in menswear. It’s all about contemporary fashion in streetwear, and I emulated that style, but with a twist. Instead of a hoodie, I opt for the funnel neck sweatshirt and instead of distressed jeans, I go for a clean pair of slim fit, dark wash denim and suede chelseas to ground the look.

Alpha Industries MA-1 Skymaster Flight Bomber Jacket Walking Down Steps
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Sweatshirt: Burnside (similar) | Boots: Thursday Boots | Jeans: Levi’s | Watch: Casio 

WHY IT WORKS:

Elements of smart casual are at play here. Up top—the sweatshirt and bomber jacket is casual. Down low—dark wash denim and suede chelseas are smart. It’s A 50/50 split of smart and casual, which almost always works, and is one of my favorite ways to style an outfit.

Alpha Industries MA-1 Skymaster Flight Bomber Jacket In Front of A Bridge
SHOP THIS LOOK—Jacket: Alpha Industries (on a budget) | Sweatshirt: Burnside (similar) | Boots: Thursday Boots | Jeans: Levi’s

WHEN TO WEAR IT: Spring, Fall and Summer seasons 40ºF to 60ºF.

IN THE END

I hope you enjoyed reading this article on how to wear a bomber jacket and are feeling inspired to try one on for size. If you’ve always thought it just wasn’t your thing, you may surprise yourself. After all, finding one’s personal style is a journey. And one way to help us along that path is to take bits and pieces from various sources, get inspired, and ultimately put our your spin on it.

Lastly, if you haven’t already, check out the lookbook video I created as a companion piece to this article.

Cheers to your style!

—K


All photos are courtesy of Erica Torres, Founder of ETPhotography.

WHICH OF THESE LOOKS IS YOUR FAVORITE?

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  • Killer post! Love the first look, especially. Awesome photography too.