Style editor Aaron Wester of The Modern Otter shows us how to wear the Men’s Sailor Bomber Jacket

Let’s be real, if you’re buying a coat, you want it to last for years, not just a season. That goes for style and for quality. You want to be able to throw it on over whatever you are wearing and be good to go. Right?

Enter the bomber jacket. This style weapon is modeled after “bombardier” pilot jackets from the military in the 1950s, which were prized for their insulation and warmth. Originally the design dates back to brown leather flight jackets in the early 1900s, but the classic design means that these days, their call to fame is how classically stylish they always look. Bomber jackets are your answer to basically all of life’s style questions.

From sweatpants to chinos, this item goes with nearly everything. And it’s a classic! Like denim shirts or oxfords, it will never go out of style.

Denim on Denim


Spring style for men usually centers around blues and grays. They’re fresh, they’re casual, and they’re easy to pair together. To pull off an easy look for chilling with friends or a relaxed date night, go for this monochromatic blue/gray look. I like to embrace varying shades – your denim shirt can be a few shades darker than your jeans. The lighter shade of the Men’s Sailor Bomber Jacket will bring it all together and the navy ribbed jacket cuffs reinforce the navy shade in the denim shirt. I can see myself in this outfit grabbing a few beers on the way home or out to a concert, but it’s still relaxed enough to make the grade for a lazy day wandering the city.


It’s easy throw this jacket on with a pair of sneakers and head out the door. It’s also waterproof, which is a mega plus for when the weather turns south.

Chinos and Boots


To take your look from laid-back sport and into ‘meet the in-laws’ sophisticated, pair your bomber with a pair of chinos and a sweater. It shows you put more thought into your outfit and actually tried today (even though you really didn’t have to with this look).

It was crazy easy to put together this look. A blue bomber jacket goes with nearly every color of chino. I paired it with a striped sweater and grounded it with brown Timberland boots. Before bomber jacket? Just a guy going to work. After the bomber jacket? Stylish, dapper gentleman about town.


Style tip: Take advantage of the zipper that goes in both directions. Zip the jacket down, and then try zipping the bottom zipper up a few inches too. This gives the jacket a little more shape and add an extra style detail to your look. And remember, a cuff in your chino goes a long way, too.

Bombers go with everything and are an essential part of every stylish guy’s wardrobe. Invest in one and you won’t have to worry about your outfits for the rest of the cool-weather season.