Originally published June 2, 2017. Now updated with new looks.
This editorial is for the guys who want styling inspiration on how to wear a bomber jacket.
A little while 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 6 additional ways to style the ever versatile 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 I’m styling the trendy bomber jacket this season.
BOMBER JACKET OUTFIT IDEAS FOR MEN LOOKBOOK
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Take a look at and get inspired on how to wear a bomber jacket, the perfect piece for spring or fall season.
HOW TO WEAR A BOMBER JACKET 7 WAYS
LOOK 1: OREO BOMBER
Looking for how to wear a bomber jacket this spring or fall? This look is perfect for that. The ‘Oreo Bomber’ may seem stuffy for summer or even early fall, 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 when I’m feeling a little rebellious. The suede bomber is mid-weight, so it’s perfect for when the weather dips. I love the texture and patterns on this lightweight sweater. It adds dimension to the look while remaining relatively muted which is the type of style I liking these days.
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.
WHEN TO WEAR IT: Spring and Fall seasons 40ºF to 55ºF.
LOOK 2: JET SETTER BOMBER
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.
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.
WHEN TO WEAR IT: Spring and Fall seasons 45ºF to 65ºF.
LOOK 3: REFINED BOMBER
The third way how to wear a bomber jacket is a little dressy. 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”.
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.
WHEN TO WEAR IT: Spring and Fall seasons 50ºF to 65ºF.
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LOOK 4: RUGGED BOMBER
For this 4th look on how to wear a bomber jacket, I throw in a rugged twist. 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.
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.
WHEN TO WEAR IT: Spring, Fall and Summer seasons 35ºF to 55ºF.
LOOK 5: HYPE STREET BOMBER
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.
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.
WHEN TO WEAR IT: Spring, Fall and Summer seasons 40ºF to 60ºF.
LOOK 6: CASUALLY SUEDED BOMBER
I like this look for two reasons. I always say to focus on the fit first. If you can nail the fit, then even the most simple getups come off as clean and refined. In the case of the casually sueded bomber, it’s got a touch of ruggedness to it as well. A look like this is my bomber jacket outfit go-to if I had to choose one.
WHY IT WORKS:
As with previous looks, the tan suede of the bomber jacket and chelsea boots look great with dark wash jeans. The Timex watch with a clean dial and chestnut leather strap adds a simple detail that’s subdued, and still stylish. As a whole, this is my favorite of all the bomber looks in this editorial.
LOOK 7: CHILL SKYMASTER BOMBER
I’m back at it again with the MA-1 Skymaster bomber jacket from Alpha Industries. This time, instead of the funnel neck sweater, I’ve got an even simpler, cleaner, grey sweatshirt instead of the funnel neck. This one is a classic spring or fall outfit featuring the lightweight bomber jacket.
WHY IT WORKS:
It works for every reason most of the other getups in this article does. The fit is proper, the color palette is versatile, and the pieces are classic.
IN THE END
I hope you enjoyed reading this editorial 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!
All photos are courtesy of Erica Torres, Founder of ETPhotography.
WHICH OF THESE BOMBER JACKET LOOKS IS YOUR FAVORITE?
Leave a comment down below or let’s continue the discussion over in the Gentlemen Within Private Facebook Community.
Looking forward to hearing from you.
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